A visitor’s guide to biking in Chicago


A view of downtown from Promontory Point, about 55th Street and the Lakefront Trail. 

Back in 2008, Momentum magazine invited me to write a roundup of the Chicago bicycle scene. The current issue of Momentum features this new guide to biking in Chicago, especially geared for visitors to the city but hopefully of interest to locals as well. Comparing the two pieces shows there have been a lot of exciting developments here in the last three years! Print space was limited so I couldn’t include every great cycling event, not-for-profit, bike shop, etc., that I would have liked to, but feel free to to comment if you think I left out anything crucial.

The city of Chicago by the numbers, courtesy of the Chicago Department of Transportation Bicycle Program:
2.7 million people
227 square miles
.5 miles of car-separated cycle tracks
123 miles of on-street bike lanes
33 miles of marked shared lanes AKA “sharrows”
50 miles of paved, off-street bike paths
12,265 on-street bike parking racks, more than any other U.S. city
60,000 people educated about safety by the city’s Bicycling Ambassadors in 2010
100 B-cycle bike share vehicles at six kiosks
300 parking spaces, showers and lockers at the Millennium Park bicycle station


The Millennium Park bicycle station, also known as the McDonald’s Cycle Center.

Cobalt, turquoise and emerald are the colors of the sky, the water and the land as seen from Chicago’s Lakefront Trail. This 18.5-mile paved greenway hugs the Lake Michigan coast, linking the bustling downtown Loop to many parks, beaches and neighborhoods. It’s great for a car-free commute or dreamy cruise, especially on its quieter South Side section, where the only distractions are the sound of R & B and scent of Polish sausages drifting from barbecues.

The path is just one of the reasons America’s third-largest city is a great bike town. “Biking is the easiest and quickest way to get around Chicago,” says Dottie Brackett, who blogs about stylish cycling at Let’s Go Ride a Bike. “The streets are flat and laid out in a grid, and many have bike lanes or ‘sharrows.’ Bicycling puts the best of Chicago at your fingertips, while you avoid traffic jams and crowded ‘L’ trains.”


Dottie Brackett. Photo courtesy of Let’s Go Ride a Bike.

New mayor Rahm Emanuel promises biking is about to get even better. His transition plan calls for expanding the city’s bike share network to thousands of cycles and building the Bloomingdale Trail, a 2.65-mile elevated rails-to-trails, within four years. He’s also committed to creating 100 miles of cycle tracks in his first term. The city completed the first half-mile just after he took office, on Kinzie Street next to the fragrant Blommer Chocolate factory.

With ever-improving infrastructure, it’s no surprise bike-to-work trips doubled in Chicago over the last decade. Traffic counts show a 22% rush-hour bicycle mode share on Milwaukee Avenue, nicknamed the “Hipster Highway” because it leads northwest to the trendy, bike-crazy neighborhoods of Wicker Park and Logan Square. The buzzing six-way intersection of Milwaukee, North and Damen avenues in Wicker Park recently received city’s first on-street bike parking corral.

A few blocks west, the Handlebar restaurant is a hub for the city’s blossoming bicycle culture. Decorated with vintage bike posters and barstools made from old rims and inner tubes, it features craft beers on tap and veggie entrees like peanut stew and blackened tofu fajitas. The leafy back patio, called the Tooker Gomberg Memorial Garden, honors the Toronto environmental activist and brother of City of Chicago bike coordinator Ben Gomberg.


Back patio at the Handlebar

On the South Side, in the Little Village community, Working Bikes Cooperative is another key hangout. One of four community bike shops spread across the city, this warehouse space offers dozens of rehabbed rides for sale and well-organized spare parts to pick through, plus repairs. Proceeds are used to ship containers of bikes to sister organizations in developing nations. There are also lots of great for-profit, commuter-focused shops in town, including three specializing in European-style city bikes.

Besides the lakefront, adventurous cyclists should take a spin on the tree-lined Chicago Boulevard System, recommends Rubani Shaw, a board member with the Active Transportation Alliance. “The boulevards connect some of the best parks and attractions, like the Japanese garden in Jackson Park and the Garfield Park Conservatory,” he says.


Rubani Shaw at the Kinzie Street protected bike lane (cycle track). 

For group rides, check out Chicago’s huge, friendly Critical Mass, plus family-oriented Kidical Mass parades and ladies-only Critical Lass pub cruises. The Chainlink, a local networking site with 5,000 members, lists many more public events, from Slow Bicycle Society picnic outings to rowdy Midnight Marauders rides.

Whatever kind of city riding you like, you’ll find it in this Midwestern metropolis. And while Chicago’s bike scene may be a bit less fashionable than on the coasts, you’ll find it down-to-earth, enthusiastic and welcoming.

Visitors’ guide

Chicago really shines in summer, when the beaches, free concerts in Millennium Park, and neighborhood festivals offer great cycling destinations. But spring and autumn can be beautiful times to ride here too, and the Bike Winter organization celebrates cold weather cycling with clinics, arts events and snow rides.

The easiest way to sample some of the city’s best cycling is a spin on the lakefront. For an urban escape, ride the CTA Blue Line northwest with your bike towards the North Branch Trail, which meanders 17 miles through deer-populated forest preserves to the Chicago Botanic Gardens.

Meets (rides and events)


The Racketeers at the Schubas Tavern Bike Bash. Photo by Justin Savage


The Handlebar (2311 W. North Ave.)

Maxwell Street Market (Desplaines St. and Roosevelt Rd.)
Sundays 7 am – 3 pm year-round. This historic flea market has the best street food in town, live blues, used books, records, bicycles and more.

Nana Café (3267 S. Halsted St.)
This sunny cafe near features local, organic ingredients and offers a free bike valet during Bike n’ Brunch events.

The Wormhole (1462 N. Milwaukee Ave.)
This 80s-themed café has a DeLorean parked in the window but gives free coffee to cyclists from 7-9 am.


The Wormhole coffeeshop in Wicker Park.

Lula Café (2537 N. Kedzie Blvd.)
This critically-acclaimed “localvore” eatery next to Boulevard Bikes (where I work) is great for a lazy brunch or romantic dinner.

Revolution Brewing (2313 N. Milwaukee Ave.)
A kid-friendly brewpub with upscale food, owned by Friends of the Bloomingdale Trail founder Josh Deth.

Signature Lounge at the John Hancock Center (875 N. Michigan Ave.)
Lock to the Pi-shaped racks in the plaza then ride the speedy elevator to the 96th floor for cocktails with jaw-dropping views.


The James Chicago (55 E. Ontario St.) – A stylish hotel offering guests free use of Paul Frank bicycles.

Park Hyatt Chicago (800 N. Michigan) – This luxury hotel lets guests check out Trek hybrids for free.

Longman and Eagle (2657 N. Kedzie) – Sleek, affordable guestrooms in bike-friendly Logan Square. Guests receive tokens for bourbon shots at the gastropub downstairs.

Streets (rentals)

B-Cycle Chicago

Bike and Roll Chicago – operates the Millennium Park bicycle station (239 E. Randolph), with rentals, repairs and showers, plus several lakefront rental locations. Guided tours available, including the Presidential Tour of Obama landmarks.

Bobby’s Bike Hike (465 N. McClurg Ct.) offers downtown rentals and tours like the Bikes, Bites and Brews Tour sampling deep-dish pizza and Chicago-style hotdogs.

Streets (shops)

Working Bikes Cooperative (2434 S. Western Ave.)

Blackstone Bicycle Works (6100 S. Blackstone Ave.)
Community bike shop in the Woodlawn neighborhood


Staff and students at Blackstone Bicycle Works

West Town Bikes (2459 W. Division St.) – Humboldt Park’s community bike shop

The Recyclery (7628 N. Paulina) – Community bike shop in Rogers Park

J.C. Lind Bike Co. (1311 N. Wells St.) – Dutch-style city bikes and bakfiets cargo bikes.

Copenhagen Cyclery (1375 N. Milwaukee Ave.) – European bicycles by Velorbis, Abici, Batavus and Larry vs. Harry.

Dutch Bike Company Chicago (651 W. Armitage) – City bikes by Linus and WorkCycles in a gallery-like setting.

Uptown Bikes (4653 N. Broadway St.)

Roscoe Village Bikes (2016 W. Roscoe St.)

Rapid Transit Cycle Shop (1900 W. North Avenue, 1305 S. Halsted)

Blue City Cycles (3201 S. Halsted)

Bubbly Dynamics (1048 W. 37th St.) – Home to several bike businesses including Lloyd Cycles, Humble Frameworks, UV MetalArts and Pedal to the People, a mechanic who makes house calls.

Seeks (Websites and other info resources)

Published by

John Greenfield

John has lived in Chicago since 1989 and has worked a number of bicycle jobs, from messenger to mechanic to managing the Chicago Department of Transportation's bicycle parking program, arranging the installation of over 3,700 bike racks. He writes regularly for Time Out Chicago, Newcity, Momentum and Urban Velo magazines and works at Boulevard Bikes in Logan Square.

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