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Top Experiences in Chicago Picasso (The Picasso)

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Travel Curious

Chicago Highlights Private Half-Day Walking Tour, with Perks

USD 200

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicago life together with an in-depth knowledge of its character.

As you journey down the Magnificent Mile, you will learn how Chicago has earned each of its nicknames, including the City of Broad Shoulders, the Second City, and of course, the Windy City. Lastly, your guide will escort you to the Hancock Tower to bid on your adieus.

You will then travel to the top of the Hancock Tower’s Observation Deck, where you can enjoy 360-degree views of the entire city at your own leisure.
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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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Tours by Doorways Of Chicago

Chicago Loop Small Group Walking Tour

USD 45

Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco buildings, all masterpieces in their unique & individual ways, as well as 4-5 other notable properties and outdoor sculptures on this fun and fabulous walk of Chicago's Financial District and parts of the North Michigan Avenue corridor. Your tour guide, interior designer, and historical architecture guru Ronnie Frey will paint a picture you'll not soon forget of modern life in the New Machine Age.
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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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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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Joe Goldman

Architectural and Historical Private Tour in Downtown Chicago

USD 199

To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus trying express? I do know a lot about this. Thus, you will gain this information about each point of interest. I have taken other tours here, and I just do not hear a word from that point of view. This tour will be like an open history book to an America that no longer exists: Roman and Greek architectural styles, as well as French and British-influenced styles. Of course, you will see the latest in office building architectural styles from around the world, for those of you who just love the modern era as well.
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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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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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L Stop Tours

Walking Tour of Chicago Pilsen Neighborhood

USD 65

Meet your tour guide at the beautiful Chagall Four Seasons mosaic as we begin our Creativity & Community neighborhood tour. After a short walk, we'll catch the Pink Line at the renovated Quincy L station (opened in 1897) and make our way to Pilsen — a vibrant neighborhood just southwest of the Loop originally settled by Czech immigrants. Pilsen ranks #10 on the Forbes magazine list of the "15 Coolest Neighborhoods in the World."

Upon arrival in Pilsen, we'll take a break and grab a taste of authentic Mexican cuisine. Afterwards, we'll stroll the neighborhood where we'll view numerous public murals and learn about the architecture that is unique to Pilsen.

We'll arrive at the renowned National Museum of Mexican Art and experience it's changing and permanent exhibitions. After that, we’ll hop back on the Pink line train to the Loop and wrap things up at the famous Picasso sculpture in Daley Plaza.
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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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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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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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ForeverVacation

Private & All-Inclusive Chicago Downtown Highlights Walking Tour

USD 223

On this private walking tour our expert local guide will take you to see some of Chicago’s best-known attractions!

The day will begin with you meeting with your friendly local guide at Millenium Park, home to Cloud Gate.From there, your tour will begin as you start your walk through Chicago, exploring the most famous and beautiful locations in the city!
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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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Inside Chicago Walking Tours

Chicago Architecture Tour: Underground Pedway and the Loop

USD 35

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!
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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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WALKIN' WITH COLIN - A*SHOW*ON*THE*GO!

Walkin' with Colin: Chicago History, Mystery, Comedy, and Tragedy

USD 44

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our loop around "Da Loop" we will peel back the layers of this Great Big Onion Town, going in and out of extraordinary buildings, admiring amazing art and architecture along the way as we uncover how it all came to be. Expect an engaging, entertaining and wide-eye-opening tour du jour of my sweet home, Chicago.