An outsider’s Chicago bike itineraries


Photo by Alan Scott Walker

This guest post was submitted by Tim Eyre, who crosses the country frequently for his job as a manager with Extra Space Storage. Eyre is a cycling enthusiast and he’s found that exploring the cities he visits via bicycle is a good way to connect with and learn about the communities he visits. He offers the following bike route suggestions for visitors to Chicago, but locals may find them interesting as well.

Chicagoans, don’t take what you have for granted. My weekdays are spent on the road, and it’s sheer grace that I discovered bicycling to keep me sane a few years back. Wherever I’m working, I can always find an escape by cruising the town on two-wheels. As any cyclist knows, the disconnect between the observer and the community that car travel creates quickly fades away when you’re self-propelled and out in the open air. Neighborhoods come alive, and we actually meet other people.

Of all the cities I regularly ride in, Chicago may be the best. The 18.5-mile Lakefront Trail is obviously the heart of this city’s bike scene, and understandably chock-full of locals and visitors like myself taking in the view. Recently, however, I’ve been branching out, taking advantage of the city’s interactive bike map, a tool that urbanites in other metropolises across the globe would drool over. If you’ve never checked it out, it details roads with existing bike lanes, shared lanes, and recommended routes.

With a little pre-planning and my GPS-equipped phone in my pocket, I’ve been discovering new favorite rides across Chicago, from Bucktown to Little Italy. Whether you’ve got an hour after work or a full day to explore, here’s my outsider’s suggestions for a perfect ride.

The Mid-City Ride

(Here’s a Google map of the route.)

Beginning at Navy Pier, which is located in the dead center of the Lakefront Trail and provides a panoramic vista of the skyline, head west on Grand Avenue (530 N.) At Wells Street (200 W.), take a left and head south. At Kinzie Street (400 N.), turn right and cross the river to Milwaukee Ave (600 W.) You’ll pass three bike shops and a handful of offbeat eateries on your way to Bucktown, where I love to deviate from the itinerary a bit and explore the funky mix of cafes and boutique shops clustered around Milwaukee/North/Damen.


Big Star tacqueria near Milwaukee/North/Damen – photo by Beast and Bean

Take a right on Damen Avenue (2000 W.), pass Churchill Field Park, and turn right on Cortland Street (1900 N.) Cortland winds past residential streets before veering left and becoming Racine Avenue (1200 W.) After that happens, take your first right onto Armitage Avenue (2000 N.), which will scoot you past more fun shops, bars, and eateries, until you come to Lincoln Park. There you can follow paths past the Lincoln Park Zoo to a bike/ped bridge over Lake Shore Drive, turn right on the Lakfront Trail and head south past Oak Street Beach on your way back to the pier.

The International North

(Here’s a Google map.)

Whether you’re starting from the Navy Pier or continuing the Mid-City Ride, you can pick up Clark Street (200 W.), a road with bike lanes, where Armitage meets Lincoln Park. After about two miles, you’ll reach Wrigley Field. Can you smell the excitement? Maybe it’s just hot dogs.

Enjoy the freedom the bike gives you to explore this Cubs-centric neighborhood before heading west on Addison Street (3600 N.). You’ll can turn right on Lincoln Avenue (1900 W.) after a mile, which will comfortably bring you to Lincoln Square, perhaps the nicest district for bike exploration in Chicago.

Turn left onto Wilson Avenue (4600 N.), crossing the river before turning right onto Manor Avenue (2800 W.) At Lawrence Avenue (4800 N.) you’ll come to River Park, an excellent place to take a break and relax before beginning the journey back. You’re now in Albany Park, a melting pot district drawing immigrants from around the world. Two of my favorite spots are right along Lawrence. Nhu Lan Bakery, 2612 W. Lawrence, is easy to pop into for a bánh mì Vietnamese sandwich, or turn your bike ride into date night with a sit down dinner of Bosnian cuisine at Sarajevo Restaurant, 2701 W. Lawrence.


Nhu Lan Bakery

When you’re done exploring Albany Park, head north through River Park on a path along the west side of the river, turn right at Argyle Street (5000 N.) and turn left of a path along the east side of the river, continuing to Foster Avenue (5200 N.) Turn right on Foster and ride three miles east to the lake, where you can pick up the Lakefront Trail, which you can follow back to Navy Pier or wherever you began.

Obama’s House

(Here’s a Google map.)

Is seeing President Obama’s house exciting enough to bother planning a special trip there? Probably not, politics aside. But there’s no reason it shouldn’t be a highlight of a bike tour through Hyde Park and Kenwood, two neighborhoods that are altogether pleasant for a South Side jaunt. It’s a solid eight miles from Navy Pier down to Hyde Park, but an easy ride if you take your time following the lakefront, passing Buckingham Fountain along the way from Navy Pier.

When you reach 47th Street, cross the bike/ped bridge over the Drive and head west down 47th. Head south on Woodlawn Avenue (1200 E.) turn left and you’ll soon hit Hyde Park Boulevard (51st Street). Head west one block to Obama’s house, 51st and Greenwood (1100 E.) Unfortunately, Greenwood is closed off to the public by security guards in an SUV and trees and hedges prevent block your view of the mansion, but you can continue west to Washington Park, where you’ll sometimes see vendors hawking Obama souvenirs.


Obama’s house – photo by Alan Liu

Take curving Payne Drive (800 E.) south through the park to Laredo Taft’s dramatic Fountain of Time sculpture. From there you can take the Midway Plaisance east past the Gothic spires of the University of Chicago continues the greenway back to Jackson Park, where paths behind the Museum of Science and Industry will lead you back to the Lakefront Trail, making this one of the nicer loop rides in any big city, anywhere.

Whether you’re a Chicago native, a newcomer, or simply visiting, this is a great place to explore on two wheels. I’m always excited to come back, since every time I visit there are new routes to discover.

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.

6 thoughts on “An outsider’s Chicago bike itineraries”

    1. How about writing up a guest post outline a bike itinerary to/around the Garfield Park neighborhood, including highlights like the conservatory and Ruby’s Soul Food, 3175 W. Madison, where Martin Luther King Jr. used to eat when he was campaigning for fair housing in Chicago?

    1. According to the Chicago Neighborhood Map (put out by a realtor), Rockwell is the western border of Lincoln Square, so they say that these businesses are in Ravenswood. Of course, neighborhood names are matters of opinion whereas Chicago Community Areas (CCA) are an official city designation, and you are correct that the Lincoln Square CCA does include everything east of the river. However, since the Lincoln Square CCA also includes an area most people would call Andersonville, perhaps using the CCA is not that useful in this context. I feel that these two businesses have more to do with the Albany Park’s Lawrence Avenue melting pot than the gentrified Lincoln Square business district. So I guess it’s a partly a matter of opinion whether you consider them to be in Lincoln square, Albany Park or Ravenswood, but officially, yes, they’re in the Lincoln Square CCA.

      1. I live at Lawrence and Fairfield and always considered my neighborhood to be Lincoln Square.  I don’t think anyone would consider it Albany Park.  Very diverse businesses in the area like Albany Park…

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