Chicago: Ultimate City Attractions Bike Tour

Discover Chicago the way it was meant to be experienced—outdoors, up close, and full of life—on our Ultimate City Chicago Bike Tour, one of the most exciting & memorable things to do in Chicago. This ride is the perfect introduction to the city's iconic sights, rich history, & stunning lakefront views.

This Bike Tour in Chicago is designed to be easy, comfortable, and enjoyable for all ages and skill levels. With mostly flat terrain and a relaxed pace, you can simply enjoy the ride while taking in the city's famous scenery. Along the way, you'll pedal through beautiful parks, plazas, and scenic waterfront paths while experiencing some of the most famous Chicago attractions.

Your adventure begins along the sparkling shores of Lake Michigan. Feel the refreshing lake breeze as you cruise along Chicago's legendary Lakefront Trail, widely considered one of the most beautiful urban bike paths in the world. From here, the city's famous skyline unfolds before you, offering breathtaking views that make this Chicago Bike Tour unforgettable.
One of the highlights of the tour is Buckingham Fountain, one of the largest fountains in the world. Watch as its dramatic water displays soar high into the air with the Chicago skyline creating the perfect backdrop. Nearby, you'll ride through the lush landscapes of Grant Park and Millennium Park, home to some of the most recognizable landmarks in the city.
At Millennium Park you'll encounter one of Chicago's most beloved attractions—Cloud Gate, better known as “The Bean.” This iconic sculpture reflects the surrounding skyline and energy of the city, making it one of the most photographed spots in Chicago.
Your ride continues through Museum Campus, where the Field Museum, Shedd Aquarium, and Adler Planetarium stand proudly along the lakefront. As you cruise past these world-renowned institutions, your guide will share fascinating stories about Chicago's history, architecture, & cultural treasures.

Throughout the tour, our passionate local guides bring the city to life with engaging storytelling, insider insights, and plenty of humor. You'll learn about Chicago's architecture, culture, sports, and legendary characters while seeing the city from perspectives most visitors never experience.

One of the best parts of this Chicago Bike Tour is how easy and stress-free it is. All bikes, helmets, and child equipment are included, so families, couples, & travelers of all ages can simply show up ready for adventure.

With Bobby's Bike Hike, you're not just along for the ride—you're part of a legacy. As America's first city bike tour company, we've been featured by USA Today (Top 10 Tours in America), TA (Top 20 Tours in the World), & Yelp (Top 15 Vacation Ideas in the USA).

If you're looking for unforgettable things to do in Chicago, this Bike Tour in Chicago is the perfect way to see the city's top attractions, enjoy spectacular lakefront scenery, and experience the energy of Chicago in a fun, relaxed, & memorable way.