Cycling in Chicago

Select Local Merchants

The exposed-brick walls of Iron Cycles speak to the straightforwardness of its employees, who prefer to focus on riding, not attitude. This judgment-free approach leads to unbiased treatment for every cycle. The staffers treat well-worn heirlooms with the same degree of care and dignity as they do snazzy titanium builds or a custom-crafted commuter. Perhaps their respect for bike diversity stems in part from their disparate cycling backgrounds: founder Brandon is an off-road racer, Ben was a bike messenger, and Steve has more than 25 years of both pedaling and mechanic experience.

Regardless of the bike brand or model, each of the shop’s services adheres to the mission of safer, savvier trips. Repairs address basic adjustments as well as complete overhauls, furnishing customers with new saddles, kickstands, and even handmade tires imported from overseas. The staffers oversee fitting sessions that fine-tune parts to suit the bike's function and the owner's body type. They can also build custom cycles that correspond to clients' goals, whether they want a frame that can hit high speeds or wheels that can store several decks of playing cards at once.

3136 W Montrose Ave
Chicago,
IL
US

With a fleet of futuristic segways and classic beach-cruiser bicycles, Bike and Roll Chicago outfits travelers with wheeled transportation to explore the city's paved surfaces. Tour guides lead groups through Millennium Park and along the lakefront to catch the skyline when illuminated by sunrises or backlit by one of Chicago's many moons. Misty Lake Michigan breezes ruffle riders' hair peeking through helmets as they pass by sailboats swaying lazily in the harbors and fishermen casting lines for trout and perch. Bike and Roll Chicago designs routes around classic architectural landmarks such as the Shedd Aquarium and Field Museum as well as popular neighborhoods home to a number of restaurants and art festivals.

316 North Wabash Avenue
Chicago,
IL
US

Bike and Roll Chicago's staff dispatches clients on wheel-based expeditions throughout Chicago. Guides—several of whom are Chicagoland natives—can lead informative and entertaining tours in Spanish, Mandarin Chinese, and semaphores.

5200 North Lake Shore Drive
Chicago,
IL
US

Chicago Rickshaw releases its fleet of pedal-powered, open-air cabs through the thoroughfares of the city, meandering up to three weary travelers on a one-hour jaunt of urban sightseeing. Rickshaws provide a distinct vantage point and remain an environmentally chummy mode of transportation second only to attaching one end of marionette strings to your legs and the other end to methodically flying pigeons. Up to three gallivanters, plus the driver, can fit in the motorless coach as it lopes small groups around the City of Big Shoulders and through many of its public easements, including areas not accessible to large motor-propelled carriages.

2333 North Seeley Avenue
Chicago,
IL
US

Inspired by a love of fitness and a passion for travel and tourism kindled within him by his late father, Jeremy Lewno founded Bobby's Bike Hike to create an interactive Chicago biking experience. He named the company after his dad, Bob, an Arkansas bus-tour operator who taught him to focus on service quality over quantity. That advice has clearly paid off, as the business's guided tours have earned a number one ranking for activities to do in Chicago on TripAdvisor and the title of Best Organized Bike Ride from the Chicago Reader in 2010.

During the tours, which include rented bicycles, guides lead groups of about 20 riders past Chicago icons in Millennium Park and on the Museum Campus, or direct them to samples of pizza, hot dogs, cupcakes, and beer in and around Wrigleyville. The crew has designed a Tike Hike tour for kids 10 and younger, a Chicago gangster tour that uncovers Chicago's seedier side, and a mansion-studded lakefront tour, during which riders may glimpse Oprah waving or handing out complimentary helicopters at her main residence. Patrons can also rent Schwinn, GT, and Cannondale Comfort bikes, mountain, road, cruisers, and tandem bikes to explore the city on their own.

465 North McClurg Court
Chicago,
IL
US

In a shop lined with more than 100 bikes models from all around the world, Upgrade Cycle Works' pro mechanics channel their love of cycling whether they are aligning the frame on an old single speed or fitting guests for a brand new road bike. During the fit process, staffers employ the same computerized system used at the Olympic training center as opposed to tracing your body outline on a large piece of construction paper. Next, they’ll help guests choose from bike brands such as Felt, Masi, and Raleigh, and an in-store selection of rides that includes road bikes, single speeds, and hybrids.

In Upgrade's workshop, pro mechanics perform comprehensive tune-ups and repairs, revitalize faded paint jobs, replace punctured wheels, and align frames. The staff also hosts repair clinics to teach cyclists how to fix flat tires and adjust brakes.

1130 W Chicago Ave
Chicago,
IL
US

Groupon Guide