CHICAGO · ILLINOIS
The best of Chicago.
The 15 best cycling tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Ride 13 miles through Chicago on day or night routes, stopping for deep-dish pizza, Chicago dogs, sweets, and optional beer.
Most Popular“We had a great experience with Joe as our guide! Great view of the city and great local food. Highly recommend!!”
Pedal Chicago lakefront neighborhoods on a 3-hour small-group bike tour with bikes and helmets included, plus free zoo and beach stops.
“So many different neighborhoods with unique histories close to downtown. Guides Fran & Dan kept our group together and explained about the fire of course, the World's Fairs, Abe Lincoln's lucky shoe & why his statue is so tall, Hugh Hefner's former mansion - and so much more! There was a bit of street construction,…”
A 3-hour Chicago bike tour for $59, riding mostly bike paths along Lake Michigan and major museums, with time for photos and stories.
“We had a fantastic time on this tour. Got to see a lot of sites, and learned some fun facts about the city along the way. AJ was our guy and is such a fun, and funny tour guide. This was our favorite of the 3 tours we did in Chicago.”
Bike Chicago’s neighborhoods for pizza, hot dogs, brownies and beer. Day ride to Wrigley Field; night show at Buckingham Fountain light show.
“We had so much fun on this tour. It was the perfect amount of biking and eating and a perfect way to explore the city. Shout out to Joe for making it such a great experience.”
3-hour guided Chicago classic food walk with deep-dish pizza, hot dogs, Italian beef, brownies, plus free 2-hour bike or kayak rental.
““Thank you Mickey for such a fantastic culinary tour of Chicago! Every stop was a delightful experience, from the delicious bites to the fascinating stories behind each dish. It was a perfect way to explore Chicago’s rich culinary diversity. Highly recommend to anyone looking to experience the city’s vibrant flavors!””
Ride Chicago’s lakefront neighborhoods in 3 hours: Lincoln Park Zoo, Old Town, Gold Coast mansions, and beach views with a local guide.
“Our tour guide, York, made for a very enjoyable afternoon!”
Ride Chicago’s West Side by bike and eat a lunch’s worth of tastings in small-group neighborhoods like Wicker Park and Ukrainian Village.
“This was a great way to see the city, have some tasty bites, and get a little light cardio in for the day. I’ve been to Chicago many times and hardly ever leave the loop so it was great to see the neighborhoods. Wyatt was a great tour guide and had fun facts plus music…”
A 4-hour Chicago bike-and-food tour hitting the lakefront, parks, riverwalk, Navy Pier, and classic tastings like deep-dish pizza.
“Seeing the different neighborhoods while riding a bike and tasting different foods.Great activity for the whole family.”
Rent a bike for a full day in Chicago and chart your own route along the Lakefront Trail to Navy Pier, parks, museums, and Wrigley Field.
“Consiglio vivamente di fare l’esperienza in bici lungo la pista ciclabile del lago. Un metodo per vedere tanto in poco tempo. Abbiamo sfruttato appieno la giornata, grazie alle bici. I nostri figli 14 e 12 anni felicissimi. Visitato tutti i parchi lungo il lago senza grossi sforzi.”
Bike Chicago in 3 hours from $59: lakefront skyline, Millennium Park sculptures, Museum Campus and Buckingham Fountain with a guide.
“A great and amazing bike tour!! A super nice guide. Thanks you so much! :)”
Rent a bike in Chicago’s Lakefront area and pedal your own route along Lake Michigan, parks, museums, and iconic neighborhoods.
“Tutto molto bello. Peccato che l’orario di chiusura è alle 18:30 e non alle 20:00 come indicato nella descrizione.”
Taste Polish pierogis, tacos, burgers and more on a Chicago West Side bike tour, riding the 606 and Lakefront Trail.
“Great guide (Lew). The food at the stops where ok at most. I have done food tours all over the world and this was among the worst. Would have liked less biking and more information. (Although biking was fun and safe). Only 4 stops in entire city.”
Ride Chicago’s lakefront on an electric bike with a private guide and quick photo stops at Navy Pier, Field Museum, Adler, and Buckingham Fountain.
“Getting a close view of all attractions in Chicago, while having fun on a electric bike. Our tour guide was great and he even stopped to take photos”
Pedal Chicago’s lakefront from Millennium Park to North Avenue Beach. Casual 8-mile ride with bikes, a guide, and nonstop views.
“Thanks for being my fantastic guide, dear Nora. I really enjoyed the bike tour.”
Self-guided Chicago half-day bike rental with helmet, lock, and map. Ride the Lakefront Trail to Navy Pier, The Bean, Lincoln Park, and more.
“Very fun family friendly activity on lake Michigan’s waterfront. Easy to find Bobby’s bike hike. Easy path for all types of riders.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
