Chicago's Ultimate City Bike Tour

Overview

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!

City: Chicago

Sun 08 Jun

Other dates

You can choose the date already on the booking website

Starting at $54.99

Make a reservation

Sun 08 Jun

Starting at $54.99

Make a reservation

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What's Included

Bicycle

Helmet

Tour Guide

Additional Info

Public transportation options are available nearby
Suitable for all physical fitness levels
This tour is appropriate for most ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
Please note: children must be strong, capable riders and be able to bike for 9 miles

What To Expect

Lakefront Trail

The 18-mile Lakefront Trail has been contributing to Chicago’s cycle success since 1963. The paved path provides walkers, runners, and bicyclists with a safe and fun way to travel along the Lake Michigan, for both recreation and commuting.

Field Museum

The Field Museum of Natural History is one of the largest museums in the world, famous for its expansive specimen and artifact collect. It’s also home to T-Rex Sue, the biggest tyrannosaurus rex ever fully recovered.

Shedd Aquarium

Shedd Aquarium opened in 1930 and is now home to 32,000 aquatic animals. It is one of the largest aquariums in the country, and the first inland museum to house a collection of saltwater fish.

Adler Planetarium

The Adler Planetarium is the oldest planetarium in the Western Hemisphere. It boasts three full-sized theatres, rotating space science exhibitions, and an extensive collection of space science instruments and materials.

Northerly Island

Northerly Island is a nature preserve located on the peninsula of land south of museum campus. Now in its early phases of natural development, the park will one day offer canoeing, bird watching, fishing, and camping for all to enjoy in downtown Chicago.

Soldier Field

Built in 1924, Soldier Field is the oldest NFL stadium in the United States. During the American football season, it’s the home of our roaring Chicago Bears, but the park also hosts some of the city’s biggest concerts in the spring and summer.

Grant Ulysses Park

Grant Park, lovingly known as “Chicago’s Front Yard,” is a waterfront park located adjacent to the Loop. Grant Park host some of the Windy City’s biggest culture festivals including Lollapalooza and Taste of Chicago.

Clarence F. Buckingham Fountain

When the Buckingham Fountain was built in 1927, it was the largest fountain in the world. Now the centerpiece of Chicago’s famous Grant Park, the fountain attracts crowds from all over the world to see its stunning light and water shows.

Millennium Park

Located at the northwest corner of larger Grant Park, Millennium Park is home to Chicago’s most beloved works of public art, including Cloud Gate, The Crown Fountain, and the Pritzker Pavilion.

The Chicago Theatre

The Iconic Chicago Theater marquee sign.

Daley Bicentennial Plaza

Marvel at the famous Picasso sculpture and the towering skyscrapers of the Loop

Lakefront Trail

Enjoy a gorgeous ride along the lakefront.

Museum Campus

Enjoy a bike ride through Chicago's Museum Campus

Show 10 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (166)

Elise_W

Mar 2025

The experience with our tour guide, Gabe, was fantastic!! Gabe knew the city by heart and was able to show us the treasures of Chicago. He was passionate and didn’t hesitate to adapt the tour according to our wishes, mostly focused on architecture and art. We saw all the iconic landmarks and masterpieces even the most hidden ones. Thank you Gabe for this memorable tour!

Julie C

Mar 2025

Our guide Lillian was very knowledgeable. The experience was fun for the whole family. Lillian explained history and significance of each place we stopped. The route was very scenic and beautiful as well.

W9691TDjm

Mar 2025

Great experience despite miserable weather. Very good communication from Bobby's Bike prior to the tour. We were thankful they carried on the tour even though only 2 of us signed up. Tour guide Dan was very knowledgeable and attentive to our needs throughout the tour. The bikes were fantastic and our 8 mile ride felt like just the right pace. We learned many things during the trip that helped us during the rest of this trip and will be helpful next time we're back. Highly recommended!