Top Experiences in Chicago Lakefront Trail

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.

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

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods ride is what started it all. Join one of Bobby’s expert guides on this 3-hour romp through Chicago’s beautiful North Side neighborhoods. See the ever-rising skyscrapers of Streeterville, the luxe residential property of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the Lakefront Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! Tour departs from 540 N. Lake Shore Drive, Chicago.

Taste all of Chicago’s classic eats on this 4 1/2 hour 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 13 miles (at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and 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.

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike.

Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city.

Discover more sights in a shorter time using a bike
Get a true taste of the City by the Lake following the tips of a local guide
Discover iconic neighborhoods and be entertained with historical insights.
Learn about the peculiarities of local cuisine and its origins.

The Chicago Outdoor Adventure Pass offers an exhilarating exploration of the city's outdoor attractions. You get 1/2 day (4 hours) bike rental, 2hr kayak rental & 2hr swim.

Biking: Enjoy a 20-mile car-free Lakefront Trail ride from Evanston to South Shore Culture Center. Access iconic landmarks like Millennium Park, Grant Park, Buckingham Fountain, and more.

Kayaking/SUP: Kayak or paddleboard on Lake Michigan. Ohio Street Beach, with its skyline views, is a prime spot for Instagram-worthy photos. The break wall ensures calm, clear waters, perfect for kayaking and SUP. Don't forget your camera to capture the breathtaking Chicago skyline.

Swimming: Get free VIP locker service at Ohio Street Beach, a top-rated Chicago beach. Enjoy a relaxing swim in Lake Michigan without any hassle.

Use each part of the pass at your own pace, whether in one day or over 3 days. Immerse yourself in Chicago's natural beauty, recreation, and waterfront views. It's a fantastic way to experience the city!

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!

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!

Take a detour off the beaten path, and explore the flavors of Chicago’s vibrant West Side with Bobbys's Bike Hike, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the World by TripAdvisor and Top 10 Food Tours in America by USA Today! This 4-hour guided food and bike tour is the perfect way to learn more about Chicago's neighboroods and taste authentic Chicago dishes along the way. You’ll explore the cultural cuisines of historic Fulton Market district, Ukrainian Village, Wicker Park, and Lincoln Park for toffee and ice cream. The tour finishes with a chocolate tasting in Old Town. You’ll learn the history of these beautiful neighborhoods and the tradition behind each of the dishes sampled. Ride through Chicago's gorgeous and unique neighborhoods, plus our legendary Lakefront Trail! There is no better way to explore Chicago than by bike!

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, and gorgeous Lincoln Park Zoo (free admission). This tour offers a diverse mix of nature and attractions. Top sights include: The Chicago Lakefront, Navy Pier, North Avenue Beach, Lincoln Park Zoo and the Conservatory. Easy riding and kid-friendly, great fun for the whole family!

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.