Chicago: Adults-Only Bike Tour with Bites & Lakefront Views｜United States

Come hungry — and ready to ride. This unforgettable Chicago Bike & Food Tour blends sightseeing, storytelling, and legendary local bites into one delicious adventure. Our signature Chicago Bike Tour combines the energy of a scenic Bike Tour in Chicago with the iconic flavors that make this city one of the greatest food capitals in the world. If you’re searching for unforgettable things to do in Chicago, this experience delivers the perfect mix of movement, culture, and cuisine.

You’ll hop on a comfortable bicycle and cruise through some of Chicago’s most vibrant neighborhoods and attractions while sampling the city’s five favorite food groups: Chicago-style pizza, classic hot dogs, Italian beef sandwiches, rich brownies, and beer (available with a VIP beverage upgrade). Each tasting stop is carefully selected to showcase authentic Chicago flavor, while your expert local guide shares the stories behind the foods locals love.

This is an Adults Only (Ages 16+) experience designed for those who want to explore Chicago in a fun, social, and relaxed environment. Whether you’re a visitor, a couple looking for a unique date idea, or a local rediscovering your city, this tour offers a lively and delicious way to experience Chicago from a new perspective.

Along the way, you’ll experience some of Chicago’s most iconic neighborhoods and attractions.

On the daytime Ride to Wrigley route, pedal through Wrigleyville, Gold Coast, Old Town, Lakeview, Lincoln Park, and Chicago's Lakefront Trail— areas full of historic streets, vibrant local culture, and classic Chicago charm.

On the nighttime Downtown Attractions version, the ride becomes even more magical as you glide through Chicago’s illuminated skyline, passing landmarks like Millennium Park, Buckingham Fountain, and Museum Campus glowing under the city lights.

Both routes include stretches along Chicago’s beautiful Lakefront Trail, where skyline views and cool lake breezes make the ride unforgettable.

The tour covers about 13 miles at a relaxed pace with perfectly timed breaks to eat, explore, and soak in the atmosphere. Much of the ride follows comfortable bike paths and neighborhood streets, making the experience smooth and enjoyable.

To make things simple, all bikes and helmets are included, so adult locals, couples, and solo travelers of all abilities 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 Food Tours in America), TA (Top 20 Food Tours in the World), and Yelp (Top 15 Vacation Ideas in the USA).

This Chicago Bike Tour is more than a ride — it’s a rolling celebration of Chicago’s neighborhoods, its legendary food scene, and the joy of exploring by bicycle.

Let’s roll — and let’s eat.