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Top Experiences in Millennium Park

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Bobby's Bike Hike - Chicago

Chicago Family Food and Bike Tour with Top Attractions

USD 79.99

This tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is easy in Chicago because of it's miles of bike trails, flat terrain and easy connections between attractions. We’ll be sampling from each of Chicago’s well known and unique foods -- deep dish pizza, a true Chicago hot dog, and a dessert for good measure. You’ll learn the history behind the foods and also get a taste for some of Chicago’s most popular downtown districts as we cruise through the Gold Coast, Chicago Riverwalk, Millennium Park, Buckingham Fountain, Museum Campus, Navy Pier and along the Lakefront. Whether day or night, you'll get fantastic views of the skyline and feel the city's vibrant energy. Veggie options available.
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Babylon Tours Chicago

Downtown Art of a City Chicago Semi-Private Guided Walking Tour

USD 73.14

What do the artists Picasso, Chagall, Miro, and Kapoor all have in
common? Incredible public art hiding in plain sight amidst world
famous architecture. This 2.5 hour semi-private (8 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art!

Highlights Include:
Edward Kemeys’s “Lions”
Juame Plensa’s “Crown Fountain”
Anish Kapoor’s “Cloud Gate” (The Bean)
Eduardo Kobra’s “Muddy Waters”
Pablo Picasso’s “Untitled”
Joan Miro’s “Chicago”
Alexander Calder’s “Flamingo”
Marc Chagall’s “Four Seasons”
Louis Comfort Tiffany Art Glass Creation
Augustus St. Gaudens “Abraham Lincoln”
Marcel Francois Loyau “Clarence Buckingham Fountain”
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Babylon Tours Chicago

Art of a City Downtown Chicago - Exclusive Guided Walking Tour

USD 73.14

What do the artists Picasso, Chagall, Miro, and Kapoor all have in
common? Incredible public art hiding in plain sight amidst world
famous architecture. Tour Chicago in a small group perfect for busy
sidewalks and get up close to monumental art! Join one of our expert guides on this unique and exclusive 2.5 hour guided walking tour of Downtown Chicago.

Highlights Include:
Edward Kemeys’s “Lions”
Juame Plensa’s “Crown Fountain”
Anish Kapoor’s “Cloud Gate” (The Bean)
Eduardo Kobra’s “Muddy Waters”
Pablo Picasso’s “Untitled”
Joan Miro’s “Chicago”
Alexander Calder’s “Flamingo”
Marc Chagall’s “Four Seasons”
Louis Comfort Tiffany Art Glass Creation
Augustus St. Gaudens “Abraham Lincoln”
Marcel Francois Loyau “Clarence Buckingham Fountain”
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Jupiter Legend Corporation

5 Day Tour On Lakes Superior Huron and Michigan

USD 1128

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron.
Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste.
Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world.

Room Details
All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers.

One Room Selection
If you are a party of more than four guests or desire to have separate rooms, please create separate bookings.

Avoid traveling in a different bus?
If you have more than one booking, please provide all confirmation numbers once your bookings are complete.
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Walk with Action

Self-Guided Chicago Walking Tours

USD 50

Experience Chicago's charm with the Self-Guided Chicago Walking Tours. Dive into the stunning Millennium Park, pose by the iconic Cloud Gate sculpture, and escape urban chaos in this celebrated green space. Transition to a serene stroll along the Riverwalk, where unique architecture lines the water's edge, each building telling a story. This combo tour is your ticket to explore, understand, and fall in love with the intricate beauty of the Windy City at your own pace.

After booking, you can check your email before downloading the Tour Guide App by Action, enter your unique password, and access your tour. The preceding steps require good internet/wifi access. Follow the audio instructions and the route from there.

This is not an entrance ticket to attractions along the route. Check opening hours before your visit.

New, extra validity — now, it’s yours for an entire year! Use multiple times over multiple trips!
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WeVenture

Chicago Food and Sightseeing Small-Group Walking Tour

USD 174

Join a local guide on this exploration of Chicago’s amazing food scene! Navigate through the downtown streets straight to the vendors and restaurants We love most!

As we pass by places like the Chicago Riverwalk and take in the city’s awe-some architecture, you’ll get to grips with the evolution of the city as immigrants brought their culinary influence to The Windy City. We’ll get to know generations-owned shops and the origins behind Chicago’s most beloved street eats, all the while appreciating fresh ingredients sourced locally from midwestern farms.

Among the tastings that will add up to a full meal, you will get a taste of a local street food staple, perhaps the famous Chicago-style hot dog or Italian Beef, or another local favorite. A food tour of Chicago is not complete without a bite of the iconic deep dish pizza, and we will top it off with a sweet treat with a meaningful connection to Chicago. By the end, you'll have had the full Chicago foodie experience!

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Friendly Local Guides

Chicago Food Tour with The Magnificent Mile and Millennium Park

USD 155

Wander through Chicago downtown exploring and gaining new food experience on this walking trip. Dive into the hospitable and authentic atmosphere of the city encountering interesting sights and visiting the principal city landmarks.
Be welcomed by the unique culinary tastes of the Windy City and fall in love with iconic treats, listening to the interesting historical and cultural facts from your guide.

On this walking tour of Chicago, revel in the incredible climate while visiting the most important landmarks of the city following your guide. You will also dive into the diversity of tastes exploring some typical Chicago food and drinks and enjoy a pleasant walk in good company, choosing your path depending on the weather.
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Chicago Tours

Private Custom City Tour in Chicago

USD 880

Let us put the Custom in Chicago Custom Tours. What are your must-see venues? What would personalize your excursion? We’ll plan your tour and make it happen, and also provide suggestions based on your interests.
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Opatrip.com USA

Love is in the Windy City - Chicago Walking Tour

USD 315.9

How about an unforgettable time in Chicago with your beloved? If you're looking to have the most romantic time while visiting famous attractions of Chicago, then you can't miss this walking tour! Why is Chicago called "The Windy City"? Did you know that Chicagoans call The Cloud Gate "The Bean"? Do you know why? Together with the professional tour guide you will discover so many different facts about Chicago and you will hear the most romantic stories as you walk along the beautiful and historical streets of Chicago. Fill your hearts and memories with the most beautiful views and photos of The Windy City!
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Chicago Insta Walk - Digital & Polaroid photoshoot

Chicago Small-Group Digital and Polaroid Photo Shoot

USD 129

Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and friendly walk will open Chicago for you from a new perspective!

Throughout the tour, I'll use iPhone and Polaroid cameras to capture your perfect shot. You'll receive approximately 100 digital photos, 10 of which will be color-corrected to make them truly pop. And for a unique and timeless souvenir, I'll also give you 5 Polaroid prints that you can treasure forever.
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Let's Roam

Private 2-Hour Scavenger Hunt Activity in Chicago

USD 13.08

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.
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Jupiter Legend Corporation

Chicago Essentials Full-Day Coach Tour

USD 126.9

Welcome to the amazing city of Chicago.
Check out the classical landmarks in Chicago while getting amazed by its post-modern architectures.
Discover the stories behind the city’s most significant buildings such as Cloud Gate and Chicago Theatre.
Take an in-depth tour of the city of Chicago and visit 360 Chicago for a full 360-degree panoramic view of Chicago from above.
Explore Millenium Park and Grant Park.
Itinerary:

Millennium Park & Cloud Gate (20 mins) → Grant Park (10 mins) → The Art Institute of Chicago (Optional, 120 mins) → Chicago Water Tower (10 mins) → Michigan Avenue (pass by) → Chicago Cruise (Optional, 75 mins, seasonal) → 360 Chicago (Optional, 75 mins)

We will pass by Navy Pier, Clarence Buckingham Memorial Fountain, Marina City, Trump International Hotel and Tower and Willis Tower Observation Deck.

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Bobby's Bike Hike - Chicago

Chicago Highlights Bike Tour with Classic Foods and Craft Beer

USD 89.99

Taste all of Chicago’s classic eats on this 4-hr guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which recently ranked Top 20 in the World by TripAdvisor. The journey is 14 miles (at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and a few samples of local craft beer! On the daytime version of the tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the nighttime version, you'll ride through the party districts of downtown and see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of our town, even if you only came for the beer.
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Tripshepherd USA

Private Half-Day Tour of Chicago

USD 1129

Book a fully guided and narrated private tour of Chicago - The Windy City with See Sight Tours, Chicago ’s best small-group tours (maximum 7 guests). Enjoy the efficiency and exclusive benefit of having your very own private local expert & guide to share unique stories, local insights & highlights as well as offering you personalized recommendations tailored to your groups interest in Chicago .
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WeVenture

Private Chicago TV and Movie Locations 3 Hour Walking Tour

USD 320

Whether you’re a movie fanatic or simply want to take a Chicago sightseeing tour that hits iconic landmarks, this walking tour is for you!

We’ll start our tour in the Chicago Loop, a lively neighborhood filled with incredible architecture and attractions. We’ll pass buildings that were seen in movies like Wayne’s World and The Negotiator, cross the Chicago River and salute the Marina Towers from The Hunter, then stop inside Union Station. You might recognize this historic hub from The Untouchables or Public Enemies.

While touring the Loop, we may also see filming scenes from The Blues Brothers as well as Ferris Bueller’s Day Off. Your tour guide will point out iconic Chicago buildings including the Willis Tower and – if it’s on your wish list – the famous Bean sculpture in Millennium Park.

With the help of the ‘L’, we can ride north to see filming locations for My Best Friend’s Wedding, The Dark Knight, and Planes, Trains and Automobiles. Truly a unique way to explore Chicago!
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eATLAS

Chicago Scav Hunt

USD 8

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk.
Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before!
Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later).
Some objectives have prizes so do your best to complete as many objectives correctly.
Once complete, you can view the Leaderboard to see how you did against others.
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Opatrip.com USA

Downtown Chicago Cultural Highlights Private Walking Tour

USD 315.9

Dive into "Chicago's Artsy Cultural Landmarks – Walking Tour," a vibrant exploration of the city's iconic artistic and architectural gems. Start at the Chicago Cultural Center, home to the world's largest Tiffany stained-glass dome. Stroll through Millennium Park to admire "The Bean," Gehry's Pritzker Pavilion, and Plensa's Crown Fountain. Experience the grandeur of the Palmer House Hilton lobby, a palace of French-inspired elegance. Marvel at Calder's unique sculpture in the Mies Van der Rohe Federal Plaza, a modernist masterpiece. Discover the Tiffany mosaic murals in the Marquette Building, celebrating Jacques Marquette's adventures. Conclude with Picasso's mysterious sculpture at Daley Plaza, an artwork that invites endless interpretation. This tour is your gateway to the heart of Chicago's cultural and artistic splendor.
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Deen Ajeigbe

Chicago Private Sightseeing Tour

USD 300

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.
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Bobby's Bike Hike - Chicago

Chicago Highlights: The Loop Small-Group Cycling Tour

USD 54.99

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime!
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Tour Travel & More

Chicago Private Half-Day Highlights Driving Tour

USD 481.52

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago.

Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations.

Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking.

This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide.

During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue.

Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop.

This private tour will finish off at your hotel in Chicago.
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Questo App City Exploration Game

Chicago Outdoor Escape Game: The Heist

USD 8.22

Play a city game where you will follow clues to discover amazing places and local stories in Chicago.

You’ll tour Chicago’s famous Millenium Park and learn about the iconic works of art that populate the area on your way to riches beyond your imagination.

Are you up for an adventure in Chicago?

Highlights:
Explore Chicago’s beloved Millenium Park and surrounding campuses
Enjoy breathtaking views of the city skyline and Lake Michigan
Learn about the artwork and architecture that marked Chicago’s journey from the 20th to the 21st century
Try a new type of experience, the perfect mix between a tour, an outdoor escape game, and a treasure hunt.

The city game will take you about 1.5 hours to complete, but there’s no time limit that will allow you to go at your own pace. You won't need a guide, just download the app, go to the starting point, and begin the adventure.
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carla carrasco ocampo

1 Hour Photoshoot in Chicago

USD 179

In this photoshoot you will have most iconic and important places in downtown Chicago, places where you need to have a photo with , and in a unique way with your own personal photographer.
We will have the most photogenic and beautiful places in millenium park like the pavilion, the cloud gate, also known like “the bean”, one of the bridges with skylines view, as well as the famous chicago sign, in Chicago theater, and we will ended in the vibrant river walk.
I will make you feel like a super model, and realy confident in front of the camera and you will take home amazing edited memories of your trip (50+ edited photos )
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Urban Adventure Quest

Chicago Scavenger Hunt Adventure

USD 20.52

Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walking tour. Guided from any smart phone, teams make their way among well known and overlooked gems of the city, solving clues and completing challenges while learning local history.
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Secret Food Tours & Secret Tours

Chicago: The Loop Small-Group or Private Food and Walking Tour

USD 89

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city.

You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!
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Action Day Trips

100+ Self Guided Driving & Walking Tours by Action

USD 99.99

Take a grand tour of “America the Beautiful” with this ultimate bundle of 100+ tours across the USA! Explore everything from sea to shining sea. Relive the intensity of the Battle of Gettysburg. Witness nature’s raw power and beauty at Yellowstone National Park. Unwind by the ocean along the Pacific Coast Highway. Explore the hottest streets in Manhattan and Brooklyn. And much, much more!

This bundle contains self-guided driving and walking tours of everything from historic battlefields to national parks to buzzing cities. If you want to explore all the beauty, wonder, and history this nation offers, this bundle’s for you.

The bundle is valid for 1 year from purchase.

After booking, you can check your email before downloading the Tour Guide App by Action, enter your unique password, and access your tour. The preceding steps require good internet/wifi access. Simply follow the audio instructions and the route from there.
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Chicago Tours

Private Chicago Architecture Tour

USD 880

Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern skyscraper. Chicago is so renowned for architecture that it’s the most vertical metropolis from here to Hong Kong.

On our Chicago Architecture Tour, we’ll stop at and discuss:
• Sears “Willis” Tower
• The John Hancock Building
• Gothic gems
• Magnificent Mile notable locations
• Historic brownstones
• The Frank Lloyd Wright homes of Oak Park

We offer a uniquely added value opportunity to view not only the outside, but also explore the inside of many of these infamous buildings. Our tour will satisfy the architecture style and structural tastes of the most discerning traveling.
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Chicago Tours

Private Al Capone Gangster Tour in Chicago

USD 880

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons. 

Visit the old stomping grounds of:
• Al Capone
• John Dillinger
• The Untouchables

View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre.

We bring Chicago’s true crime past to life before your very eyes.
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Shoreline Sightseeing

Chicago: Lake Michigan Skyline Sightseeing Boat Cruise

USD 37.58

Admire all of Chicago's fabulous lakefront sights and attractions on this Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing cruise.
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Chicago Tours

Chicago: Gangsters and Ghosts Tour Walking Tour

USD 35

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago!

You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.
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Yachti Charters & Tender

Chicago Waterfront Small-Group High-Speed Boat Tour

USD 90

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way!

Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!
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Chicago Travel & Tours

Private Chicago Highlights Driving Tour

USD 190

See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly from your Chicago accommodation, after which you’ll be whisked away to see the sights. From the storied Magnificent Mile to the glamour of the Gold Coast, you’ll encounter the best of the Windy City. This private tour is available in Portuguese, English, or Spanish, and kicks off promptly at 9am.
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Flytographer

Private Vacation Photography Session with Local Photographer in Chicago

USD 299

Flytographer Private Vacation Photo Shoot

Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Chicago, including where to eat & what to see from your vacation photographer. Return from your trip with beautiful, high-quality vacation photos — the best souvenir ever.

We specialize in:
- honeymoons
- family trips
- engagements
- anniversaries
- romantic getaways
- multi-generational trips
- babymoons
- solo travellers
- and just because!

With over 10,000 5-star reviews, Flytographer is the global leader in vacation photography and has captured over 3 million memories for travellers across six continents. We’ve been featured across A-list media, including Conde Nast Traveler, Oprah, Forbes, Travel + Leisure, New York Times, BRIDES, Martha Stewart Weddings, InStyle Magazine, Elle, Buzzfeed, Refinery29, Huffington Post, & many more.
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Bobby's Bike Hike - Chicago

Chicago Half-Day Walking Food Tour with Free Bike or Kayak Rental

USD 99

Ready for the ultimate day out in Chicago? We’ll embark on an unforgettable Chicago journey, where iconic flavors like Chicago Pizza, Hot Dogs, Italian Beef, Chicago-mix Popcorn, and the original Brownie await. Opt for the VIP Craft Beer package for a heightened experience. Beyond bites, our expert-guided tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more. Enjoy a 5-hour walking tour and receive a bonus 2-hour FREE bike or kayak rental, adding value to your experience. Maximize your day by biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Leave the planning to the local experts. Bobby’s Bike Hike was awarded the following three awards just this year: “Top 10 Food Tours in America” by USA Today, “Top 20 Food Tours in the World” by TripAdvisor, and “Top 15 Vacation Ideas in USA” by Entrepreneur Magazine. Seize the opportunity for the ultimate Chicago fusion of flavors and sights in a single, unforgettable day!
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Bobby's Bike Hike - Chicago

Chicago Holiday Stroll and Food Walking Tour with Samples

USD 79.99

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deep dish pizza, Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Upon arrival, you can add a VIP holiday craft beer package for $19.99/person. Our entertaining guides will get your holiday spirit primed with plenty of food and knowledge. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays!
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Bobby's Bike Hike - Chicago

Chicago Christmas and Holiday Walking Tour

USD 34.99

There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This tour is brought to you, internationally recognized tour company headquartered right here in Chicago. Our entertaining guides will get your holiday spirit primed with plenty of fun facts, general knowledge, and the best of Chicago holiday decor. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the fabulous Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. This tour is a walking tour only. No food/drinks on this particular tour.
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WeVenture

Chicago Architecture and Highlights Small-Group Walking Tour

USD 245

Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighborhoods, top attractions, and the Chicago ‘L’!

We’ll start by exploring the Chicago Loop, home to an array of mind-blowing architecture. See the Willis Tower, Union Station just across the river, and admire the Beaux-Arts beauty of the Art Institute of Chicago. No downtown Chicago experience is complete without a stop at Millennium Park’s Cloud Gate, AKA The Bean.

We’ll then head north to stroll along the Chicago Riverwalk before exploring the River North neighborhood, home of the iconic Wrigley Building.

Over in the Magnificent Mile district, grab post-tour tickets for the Museum of Contemporary Art or brave the 94 floors up to 360 CHICAGO observation deck. End your tour here or nearby in the attraction- and entertainment-filled Navy Pier.

During your tour, your guide will treat you to a local snack as well as a $5 train pass so we can really maximize our time sightseeing in Chicago!
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Bobby's Bike Hike - Chicago

Chicago Highlights Walking Tour with Free Bike or Kayak Rental

USD 44.99

The perfect tour for first timers to Chicago or those who want to explore Chicago's top attractions and highlights. Stroll through the beautiful streets of downtown Chicago and learn about the City’s rich history, colorful characters, and get insider tips. Enjoy a 2hr walking tour & receive a bonus FREE 2hr bike or kayak rental, adding value to your experience. Enjoy biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Bobby's Bike Hike walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Magazine. Explore the amazing sites that Chicago made famous; Millennium Park, Chicago Riverwalk, amazing Architecture of the Wrigley Building and Chicago Theater, & Michigan Avenue dubbed ‘the Magnificent Mile’ for it’s world-renowned shopping. Bobby’s local expert guides lead you through downtown Chicago’s most iconic landmarks and share their knowledge about the City along the way. The tour covers 1.5 miles(2.25km) on easy, flat terrain.
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VoiceMap

The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour

USD 11.99

Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour.

• Take in Chicago’s concrete giants and hear fascinating stories about quirky artworks, local tragedy, and the city’s journey to revitalisation
• Hear from producer Phil Biedron, an actor and tour guide whose passion for storytelling lead him to create this VoiceMap tour
• Do it all in two hours or linger at stops along the way with complete control over when you start and finish
• Get unlimited use before your booking date and after it
• Use the virtual tour option at home

Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code.

The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.
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History with Action

Chicago Millennium Park Self-Guided Walking Tour

USD 14.99

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you like; pausing to explore further on your own. Take in the sights of the public art—including the famous "Cloud Gate," otherwise known to locals as "The Bean"—and hear the stories behind their creation. The GPS-enabled guide will stop and start the professional commentary automatically as you explore the area.

After booking, you can check your email before downloading the Tour Guide App by Action, enter your unique password, and access your tour. The preceding steps require good internet/wifi access. Simply follow the audio instructions and the route from there.

This is not an entrance ticket. Check opening hours before your visit.

New, extra validity — now, it’s yours for an entire year! Use multiple times over multiple trips!
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Bike and Roll Chicago

Chicago Sunset Segway Tour

USD 75

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views as well as views of Chicago's world-famous skyline and graceful lakefront. This segway tour departs near Millennium Park as dusk arrives and passes sights like Buckingham Fountain, Chicago’s majestic lakefront, and the Museum Campus.
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Big Bus Tours - USA

Chicago Hop-On Hop-Off Big Bus Tour

USD 49.5

Discover Chicago's best on our Big Bus tour. Board our open-top, double-decker bus and see the city's iconic landmarks, from the Magnificent Mile to Millennium Park. Utilize our convenient stops to explore vibrant neighborhoods and attractions, including Willis Tower, the Chicago Riverwalk, and more.

Spend your day shopping on Magnificent Mile, enjoying Navy Pier's Ferris Wheel, or tasting authentic Chicago Deep Dish Pizza. Our flexible tour lets you create your own itinerary, with a free app to track bus arrivals.

Listen to digital commentary in multiple languages, offering expert insight into Chicago's history and culture, while recommending the best places to eat, drink, and shop. Offering comfortable seating and panoramic views, our Hop-On Hop-Off Sightseeing Tour is an ideal way to explore the city. Hop off as often as you like within your ticket's validity period, and simply hop on again when ready to continue.
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Chief Chicago Limo

Private Downtown Chicago SUV Sightseeing Transfer Service

USD 800

Luxury vehicles
Professional chauffeurs
Updated fleet
Licensed chauffeurs
Knowledge about navigating in the city
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Chief Chicago Limo

Chicago 6-hour Private City Driving Tour

USD 960

Luxury vehicles
Professional chauffeurs
Updated fleet
Licensed chauffeurs
Knowledge about navigating in the city
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Alley Kat Adventures

Chicago Smartphone Scavenger Hunt with Live Remote Host

USD 21.6

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment!

Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!
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Chief Chicago Limo

Chicago: Private Half-Day Downtown Tour via Luxury Sedan

USD 640

Luxury vehicles
Professional chauffeurs
Updated fleet
Licensed chauffeurs
Knowledge about navigating in the city
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See it ALL Chicago Tours

Chicago Small-Group Tour With Optional Architecture Cruise

USD 47.95

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city.
On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more!
Along the way, your guide will provide historical, informational and at times humorous commentary about the area.
Four photo stops are a part of each tour. The small-group atmosphere with a maximum of 10 people ensures a more personal experience. 

You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat.

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See it ALL Chicago Tours

Chicago City Small-Group Minibus Tour

USD 47.95

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more!

Along the way, your guide will provide historical and informational and at times humorous commentary about the area and its many attractions.
The small-group atmosphere with maximum of 10 people ensures a more personal experience.  
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Tripshepherd USA

Chicago Highlights Half-Day Small-Group Driving Tour

USD 254

Explore the Windy City with See Sight Tours, Chicago’s best small group tours (max. 7 guests).

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan .Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about the surrounding area including exclusive local insights, historic highlights and personalized recommendations.

The tour includes complimentary pick-up and drop-off, all attraction admission fees, and skip the ticket line entry - helping you avoid long wait lines and wait times and freeing up more valuable time to enjoy your vacation. Best way to see all of what Chicago has to offer in a limited amount of time!
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ForeverVacation

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

USD 236

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then this is the tour for you.
The morning will start with meeting with your friendly local guide at the meeting point. From there your tour will begin as you start your day walking throughout Chicago and exploring the most famous locations in the city.
This half-day tour will be fully packed with famous landmarks, vintage architecture, secretly located spots and much much more!
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Full schedule
10:00 AM- Meet your Guide at the Grand Subway Station
10:10 AM- Walk along Magnificent Mile
10:20 AM- Stop at Wrigley Building & admire Tribune Tower
10:50 AM- Explore Pioneer Court
11:20 AM- Explore Millennium Park & see Cloud Gate
11:55 AM- Check out an Iconic fountain
12:20 AM- Chicago Riverwalk
1:00 PM- Explore Navy Pier
2:00 PM- Get dropped off by your guide at Millennium station
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Friendly Local Guides

Deep-Dish Pizza Tour in Chicago with Local Expert

USD 135

Explore Chicago culinary delights on this food tour with your local guide. Head to the iconic landmarks and walk down the Riverwalk while discovering what culinary blend has formed in Chicago thanks to immigrants from different countries and who brought their native recipes with them. Try out local favorites as you pass by the street food stand, grab 1 or 2 Chicago-style hot-dogs or Italian Beef. Get acquainted with the best shops and cafes that have stood the test of time and have been there for generations. The tour is perfect for foodies who would like to get up close and personal with the Windy City’s unique cuisine..

• Uncover the best meals of Chicago and admire the iconic landmarks
• Learn about the origins of famous dishes and savor the moments of delight
• Follow your guide to find the best dining options in the city
• Get a bigger-picture experience diving into the culinary and cultural scene of the City by the Lake
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Friendly Local Guides

Bike Tour in Chicago

USD 129

Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive into the bustling life of the business districts, be welcomed by the soothing green of the parks, and admire the lake scenery as you ride along the shore.
The city boasts plenty of attractions and landmarks to discover, so the bike is a perfect way to save time to get there.

Visit the most important landmarks of the city following your guide. Enjoy a safe bike trip around the city and get experience mainstream tours can’t offer. Be entertained with historical and cultural insights from your guide. The tour is great for families
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L Stop Tours

Chicago Pedway and Landmarks Small-Group Walking Tour

USD 60

Take a tour of Chicago's Pedway system, a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other without encountering weather or traffic.

Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling from two unique perspectives, and make a quick stop the iconic Walnut Room.

We return to the Pedway and follow it to Civic Center Plaza for a quick look at a famous Picasso sculpture and view the Chicago Temple and it's famous Sky Chapel. Back down to the Pedway, we'll visit to City Hall followed by a short walk to a nearby L station.

A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and to Millennium Park to view the famous "Bean" sculpture, Lurie Gardens and Crown Fountain.
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Friendly Local Guides

Chicago Gangsters Tour - Colorful History and Dark Past

USD 99

Fell the tug of history and dive into the breathtaking events of the past. On this intriguing and unusual tour, you will explore another side of famous locations and get acquainted with haunted places filled with a spirit of gangsters and speakeasies of the roaring 20s.

Hear the captivating stories of Chicago’s past and feel the curiosity level rising as you immerse yourself into those times.

Discover the dark and mysterious history of the Chicago downtown
Be entertained by the expert local guide who knows the true history of the city
Get to know what lies beyond the famous Chicago facades and what is hidden from the mainstream tours
Visit the most impressive and exciting sites.
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Chicago Architecture Center

Small-Group 90-Minute Walking Tour: Architecture of Chicago

USD 30

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower, the Chicago Theatre and more!

Get a brief overview of more than a dozen buildings—as well as Chicago landmarks like Millennium Park, the Loop and the Chicago River—on this whirlwind tour. There are lots of photo opportunities along the way, so be sure to bring your camera!

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
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Intrepid Urban Adventures - USA

Chicago: Architecture, History & Highlights Small Group Tour

USD 59

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This walking tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only that, we’ll throw in a couple of sweet, local treats to keep you going as we explore on foot.
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Chica-GO Off The Beaten Path Tours

Your Way or the Highway: Private Chicago Walking Tour

USD 220

Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch.

Focus can be on public or street art, architecture, food, and much more!

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Intrepid Urban Adventures - USA

Chicago in a Day: Food, History and Architecture Walking Tour

USD 131.54

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!
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Intrepid Urban Adventures - USA

Chicago Small Group Food Tour

USD 69

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spots for some of the city’s best-loved dishes. From deep-dish pizza to Chicago-style hot dogs, this tour will leave you filled with delicious local foods as well as some insider knowledge into the city’s culinary history and culture.
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Bobby's Bike Hike - Chicago

Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More

USD 79.99

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll through the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America by USA Today and Top 20 in the world by Tripadvisor, offers this ultimate food & walking tour to explore the foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State Street, Chicago Theatre, Chicago Riverwalk, Michigan Avenue, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on calm, clear Lake Michigan.
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Absolutely Chicago Segway Tours

Chicago Highlights Small-Group Segway Tour

USD 79.99

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!
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Heli Chicago

Private 45-Minute Chicago Skyline Helicopter Tour

USD 849

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per person.)
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Friendly Local Guides

Chicago Foods Tour with The Loop, Skyline, Millennium Park

USD 145

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most prominent neighborhoods of the city and immerse yourself in its tastes and flavors.

Stroll through the Loop and Millenium Park, wander down the Riverwalk and discover iconic sights and hidden gems from another perspective.

Get inside Chicago’s life through food and connect your heart and soul to the Windy City vibe while tasting classic deep-dish pizza, dipped Italian beef, and Chicago-style hot-dogs.

• Benefit from small-group experience and undivided attention from your local guide
• Savor the classic Chicago eats and get to know the history of their creation
• Witness fascinating art objects, architecture landmarks, and beautiful cityscapes
• Get useful recommendation of where to eat and drink from your guide
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Uvamai Niche Tourism

Chicago Self-Guided Audio Tour

USD 9

Learn more about the top 15 tourist attractions in Chicago. Its history, culture, myths, architecture, and other important facts are in this audio commentary.

The top 10 advantages for those who prefer flexibility on their tour.
1. Safe - Not required to download, with just a click of secure access links it can be listened to online on any device.
2. Save - The lowest price in the city.
3. Stories - No imagination stories, only verified information.
4. Schedule - Listen at your own convenience of time, pace, and location.
5. Select - Preferred languages and attractions.
6. Self-control: No need to be behind someone's instructions in always.
7. Share - with co-travelers in just a click.
8. Soft - Selective crafted words that make you listen again.
9. Simple - Use our personally created itinerary which starts from the city's central station and then gradually moves one by one.
10. Smart - in all aspects.
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Cranberry Tours

Chicago: Escorted Bus Tours from Toronto

USD 886.37

Join Cranberry Tours for an exhilarating bus journey to the Windy City—Chicago! Our comfortable and scenic ride from Toronto will whisk you away to the heart of American urban culture. Upon arrival, immerse yourself in the architectural wonderland, with a planned itinerary including the towering Willis Tower, the historic Wrigley Building, and the art-filled expanses of Millennium Park. We'll cruise down the Magnificent Mile for some world-class shopping and dine on authentic deep-dish pizza. With expert guides to lead the way, you'll discover the rich tapestry of Chicago's neighborhoods, each brimming with stories and local flavor. This tour promises not just sights and sounds but a deep dive into the vibrant spirit of one of America's most iconic cities. Get ready for a Chicago adventure that will leave you with memories to last a lifetime!
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ForeverVacation

Chicago Highlights Private, Full-Day Driving Tour

USD 750

If you're looking for an exciting and stress-free day exploring the wonders of Chicago, then this is the tour for you. We can’t wait to show you around!

The morning will start with a private pickup from your hotel by one of our friendly, local guides. From there your tour will begin as you start your drive in one of our comfortable and spacious vehicles.

This full-day tour will be fully packed with famous landmarks, vintage architecture, secret spots and much much more!
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Full schedule
10:00 AM – Pick up from Hotel
10:15 AM – Check out Buckingham Fountain
10:45 AM – Arrive at Michigan Avenue Bridge
11:15 AM – Awe at the Chicago Cultural Center
12:15 PM – See Cloud Gate and explore Millennium park
1:00 PM – Lunch time
2:00 PM – Go to Chicago Theater
2:30 PM – See Garfield Park Conservatory
3:00 PM – Check out the Greetings from Chicago mural
3:30 PM – Snap a cool pic outside of Wrigley Field
3:45 PM – Return to hotel
4:00 PM – Arrive at hotel
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History with Action

Ultimate Chicago Self-Guided Walking Audio Tour Bundle

USD 24.99

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city!

After booking, you can check your email before downloading the Tour Guide App by Action, enter your unique password, and access your tour. The preceding steps require good internet/wifi access. Simply follow the audio instructions and the route from there.

This is not an entrance ticket. Check opening hours before your visit.

New, extra validity — now, it’s yours for an entire year! Use multiple times over multiple trips!
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Bike and Roll Chicago

Chicago: Lakefront Highlights Small-Group Segway Tour

USD 64

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!