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“Joe was fantastic! Very knowledgeable about the city and made the trip fun and safe for our entire group…”
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 $59, riding mostly bike paths along Lake Michigan and major museums, with time for photos and stories.
“Isfun , is also historical and get to know some parts of the city that you would not have visited on your own .”
Bike Chicago’s neighborhoods for pizza, hot dogs, brownies and beer. Day ride to Wrigley Field; night show at Buckingham Fountain light show.
“the all tour was excellent. highly recommend to everyone great history of Chicago and beautiful views 👌”
3-hour guided Chicago classic food walk with deep-dish pizza, hot dogs, Italian beef, brownies, plus free 2-hour bike or kayak rental.
“Some days ago, I took the Chicago Favorites Food & Walking Tour. I loved it. Not only was the food excellent, I also learned a lot from Julia, our guide, about the city. I really can recommend the tour.”
Ride Chicago’s lakefront neighborhoods in 3 hours: Lincoln Park Zoo, Old Town, Gold Coast mansions, and beach views with a local guide.
“Great way to see the city, learn some history and get some exercise”
Ride Chicago’s West Side by bike and eat a lunch’s worth of tastings in small-group neighborhoods like Wicker Park and Ukrainian Village.
“Amazing tour guide. Lovely bike ride. Great good. Lou was a really good tour guide and knows a lot about Chicago.”
A 4-hour Chicago bike-and-food tour hitting the lakefront, parks, riverwalk, Navy Pier, and classic tastings like deep-dish pizza.
“never went on bike tour, was notified evening prior that tour guide got sick offered a walking tour and wasn't really compensated the difference of over 100$, was offered a couple of 6oz beer drinks. requested the vegetarian option but didn't expect to pay that much for an order of fries!”
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.
“Peddle fell off 5 miles down cycle path. There was no follow up or compensation from company. Bike trail was great.”
Bike Chicago in 3 hours from $59: lakefront skyline, Millennium Park sculptures, Museum Campus and Buckingham Fountain with a guide.
“una experiencia infaltable para conocer la ciudad! nuestra guía muy simpática y nos contaba parte de la historia de l ciudad super recomendable lo volvería hacer”
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 time”
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.
“We had a great time with Anthony. Riding the electric bikes made the tour more fun and less work. It was nice to see part of the city from a different view.”
Pedal Chicago’s lakefront from Millennium Park to North Avenue Beach. Casual 8-mile ride with bikes, a guide, and nonstop views.
“We had no tour since they didn’t have our booking in their system.”
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.
