Chicago City Guide

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Photo by: Tom Carroll (CC BY 2.0)

Visiting Chicago

To really understand why Bicycling Magazine recently placed Chicago first on their list of the 50 best U.S. cities for cyclists, it takes a look beyond the 100 miles of new protected bike lanes Chicago has added since 2015, the nearly 600 bright blue Divvy Bike Share stations and, of course, the city’s iconic Lakefront Trail.

Accordion

Spending just a few days in Chicago, it becomes clear that this is a city built to be experienced by bike, or on foot. Wide diagonal avenues with well-marked bike lanes cut across the city’s otherwise tight grid of side streets and boulevards. Every morning, a flock of bike commuters ranging from lycra-clad roadies to fair-weather cruisers migrate down Milwaukee Avenue to jobs in the Loop. The CTA’s packed Blue Line rumbles into the Damen stop overhead, pedestrians dashing to make the train without spilling their travel mugs.

Taking in the scene, the only things not in constant motion are the cars—stuck in morning traffic, backed up for blocks. Pedaling north up Damen Avenue from Wicker Park, pass underneath the recently finished 606 Trail, a nearly 3-mile elevated trail that gives Manhattan’s High Line a run for its money. Like the High Line, the 606 (named for Chicago’s zip code prefix) is a converted railway, which has found new life as a vibrant multi-use artery through the city’s west side residential neighborhoods.

A little farther north, look out over the Chicago River from the top of the Damen Avenue bridge, the old wooden docks of stores and warehouses below a reminder that Chicago really has much more in common with cities like London, Paris, or New York than younger, highway-based American cities—structured around cars, and parking them. Getting to know the city as a cyclist or pedestrian, you’ll be amazed at how much ground you can cover in a single day, each neighborhood immersive in its own distinct flavor, architecture and local business.

From a slow Saturday morning brunch on the grassy boulevards of Logan Square, to a blustery ride along Lake Michigan south of the Museum Campus, get to know Chicago best by leaving your car parked, and letting the city’s bike paths and reliable transit system lead you straight to the heart of the action—or maybe just to the next restaurant.

This page will provide a few tried-and-true routes from a native Chicagoan and everyday cyclist, as well as some insider tips for the smoothest possible experience navigating Chicago on foot, and on the CTA. This being said, it’s important to remember that Chicago is a diverse, bustling, endlessly creative city—there’s no substitute for a bit of straying from the day’s plan, and seeing what a neighborhood has to offer.

Planning your visit

weather

Weather

Between November and February, temperatures in Chicago routinely dip below -10°F, with blizzards of lake-effect snow often taking even the most weathered Chicagoans by surprise. For the most reliable outdoor access, visit Chicago between May and October. Early Fall is also a beautiful time to take the South Shore Line to nearby Indiana Dunes State Park for a colorful hike along Lake Michigan.

transport

Public Transportation

The Chicago Transit Authority (CTA) is very accommodating of cyclists with both trains and buses allowing bicycles at no additional charge. Feel free to simply take your bike with you onto the train, outside of rush hour. Buses allow bikes at any time, carrying up to two bikes on easy-to-use front racks.

bicycle

Bike-Share Program

A 24-hour pass for Chicago’s Divvy bike-share system (divvybikes.com) allows you to use any of the nearly 600 Divvy bike stations across the city in 30-minute intervals. Tour Wicker Park, pedal to the Museum Campus, or head up to Lincoln Square. When you arrive at your destination, just find the nearest Divvy station to return your bike.

transport

Getting There

You’ll have two options when you fly to Chicago: O’Hare International Airport (ORD), located 17 miles from downtown, and Midway International Airport (MDW), about 10 miles away. Take the Chicago Transit Authority (CTA) ‘L’ Train from either airport to reach downtown. From O’Hare, take the Blue Line to downtown, a 45-minute journey; from Midway, take the Orange Line, a 25-minute trip to the city center.

Travel Resources

Check out these helpful websites for planning your travel in Chicago.

Self-Guided Tours

Things to see and do in Chicago

Tweet

5020 N Sheridan Rd., IL, Chicago,
tweet.biz

Housed in a small art-deco building just off the Lakefront Trail in Uptown, Tweet's cozy atmosphere is perfect for getting some writing done on a rainy morning, or sharing one of their award-winning...

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Tweet

5020 N Sheridan Rd., IL, Chicago,
tweet.biz
Housed in a small art-deco building just off the Lakefront Trail in Uptown, Tweet's cozy atmosphere is perfect for getting some writing done on a rainy morning, or sharing one of their award-winning Boody Marys with a few friends.

Yuzu Sushi & Robata Grill

1751 W. Chicago Ave., IL, Chicago,
www.yuzuchicago.com

This great little BYOB sushi & robata grill in West Town calls itself "Japanese Inspired", taking some delicious creative liberties with traditional cuisine.

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Yuzu Sushi & Robata Grill

1751 W. Chicago Ave., IL, Chicago,
www.yuzuchicago.com
This great little BYOB sushi & robata grill in West Town calls itself "Japanese Inspired", taking some delicious creative liberties with traditional cuisine.

West Town Bakery

1916 W Chicago Ave, IL, Chicago,
westtownbakery.com

With sustainably-sourced ingredients and lots of vegan and gluten-free options, this cozy bakery and diner does its best to be accessible to everyone in the community. Cakeballs from West Town are a...

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West Town Bakery

1916 W Chicago Ave, IL, Chicago,
westtownbakery.com
With sustainably-sourced ingredients and lots of vegan and gluten-free options, this cozy bakery and diner does its best to be accessible to everyone in the community. Cakeballs from West Town are a hot commodity, highly recommended!

New Wave Coffee

2557 N Milwaukee Ave, IL, Chicago,
www.newwavecoffee.com

Walking into New Wave Coffee makes me feel like I never left college, in all of the right ways. The checkered floor and lived-in vibe of this popular Logan Square coffeehouse makes for a great meet-up...

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New Wave Coffee

2557 N Milwaukee Ave, IL, Chicago,
www.newwavecoffee.com
Walking into New Wave Coffee makes me feel like I never left college, in all of the right ways. The checkered floor and lived-in vibe of this popular Logan Square coffeehouse makes for a great meet-up spot, or settle-in for a rainy afternoon with your laptop or novel.

Lula Cafe

2537 North Kedzie Blvd., IL, Chicago,
lulacafe.com

Lula Cafe opened its doors in Logan Square in 1999, and has since become the brunch and farm-to-table hub of the Logan Square. The patio is highly recommended, and worth the wait in the summer!

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Lula Cafe

2537 North Kedzie Blvd., IL, Chicago,
lulacafe.com
Lula Cafe opened its doors in Logan Square in 1999, and has since become the brunch and farm-to-table hub of the Logan Square. The patio is highly recommended, and worth the wait in the summer!

Davis Movie Theater

4614 N. Lincoln Avenue, IL, Chicago,
www.davistheater.com

Built in 1918, the Davis Theater is probably best known as a weathered and loved community movie theater in Lincoln Square. Recently renovated after a year of construction, the Davis has embraced its...

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Davis Movie Theater

4614 N. Lincoln Avenue, IL, Chicago,
www.davistheater.com
Built in 1918, the Davis Theater is probably best known as a weathered and loved community movie theater in Lincoln Square. Recently renovated after a year of construction, the Davis has embraced its art-deco roots with an attached 1920's-style lounge.

Old Town School of Folk Music

4544 N. Lincoln Avenue, IL, Chicago,
www.oldtownschool.org

Since 1957, the Old Town School of Folk Music has brought some of the most vital and influential performers through Chicago, as well as offering private and group classes.

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Old Town School of Folk Music

4544 N. Lincoln Avenue, IL, Chicago,
www.oldtownschool.org
Since 1957, the Old Town School of Folk Music has brought some of the most vital and influential performers through Chicago, as well as offering private and group classes.

Reckless Records

1379 N. Milwaukee Avenue, IL, Chicago,
www.reckless.com

Scratch that vinyl-collecting itch at Reckless Records' new flagship location in Wicker Park, with an overwhelming collection of records, CD's and tapes, not to mention in-store performances.

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Reckless Records

1379 N. Milwaukee Avenue, IL, Chicago,
www.reckless.com
Scratch that vinyl-collecting itch at Reckless Records' new flagship location in Wicker Park, with an overwhelming collection of records, CD's and tapes, not to mention in-store performances.

Women & Children First Bookstore

5233 N. Clark Street, IL, Chicago,
www.womenandchildrenfirst.com

Consistently one of the best-curated and most progressive bookstores in Chicago, hosting readings, book groups, and kids' storytime.

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Women & Children First Bookstore

5233 N. Clark Street, IL, Chicago,
www.womenandchildrenfirst.com
Consistently one of the best-curated and most progressive bookstores in Chicago, hosting readings, book groups, and kids' storytime.

Flat Iron Arts Building

1579 N. Milwaukee Avenue, IL, Chicago,
www.flatironartsbuilding.com

This staple of Wicker Park houses galleries, theater spaces, and artists' lofts, with regular shows and open houses.

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Flat Iron Arts Building

1579 N. Milwaukee Avenue, IL, Chicago,
www.flatironartsbuilding.com
This staple of Wicker Park houses galleries, theater spaces, and artists' lofts, with regular shows and open houses.

Johnny Sprockets

5434 N. Clark Street, IL, Chicago,
johnnysprockets.com

A mainstay of the Chicago cycling scene, Johnny Sprockets has a few locations throughout the city's north side, all offering personable, professional sales and service.

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Johnny Sprockets

5434 N. Clark Street, IL, Chicago,
johnnysprockets.com
A mainstay of the Chicago cycling scene, Johnny Sprockets has a few locations throughout the city's north side, all offering personable, professional sales and service.

Comrade Cycles

1908 W. Chicago Avenue, IL, Chicago,
comradecycles.com

A proudly employee-owned shop in West Town, Comrade Cycles stocks some of the best commuter gear in town, and is ready to tackle any kind of project, from brake pad replacements to tuning your ride...

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Comrade Cycles

1908 W. Chicago Avenue, IL, Chicago,
comradecycles.com
A proudly employee-owned shop in West Town, Comrade Cycles stocks some of the best commuter gear in town, and is ready to tackle any kind of project, from brake pad replacements to tuning your ride for next weekend's criterium.

Heritage General Store

2959 N. Lincoln Avenue, IL, Chicago,
www.heritagebicycles.com

Heritage General Store, on north Lincoln Ave., offers a bright, quiet place to get some work done over a cup of coffee, while checking-out some beautiful handbuilt frames.

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Heritage General Store

2959 N. Lincoln Avenue, IL, Chicago,
www.heritagebicycles.com
Heritage General Store, on north Lincoln Ave., offers a bright, quiet place to get some work done over a cup of coffee, while checking-out some beautiful handbuilt frames.

Village Cycle Center

1337 N. Wells Street, IL, Chicago,
villagecycle.com

One of Chicago's oldest and best-known bike shops, Village Cycle Center consistently provides solid bike-fitting services, and can have a new bike ready to ride in less than an hour.

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Village Cycle Center

1337 N. Wells Street, IL, Chicago,
villagecycle.com
One of Chicago's oldest and best-known bike shops, Village Cycle Center consistently provides solid bike-fitting services, and can have a new bike ready to ride in less than an hour.

Boulevard Bikes

2535 North Kedzie Boulevard, IL, Chicago,
boulevardbikeshop.com

This cozy storefront at the center of Logan Square is one of the few shops in Chicago that offers used bikes, as well as a great selection of commuter bikes and gear.

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Boulevard Bikes

2535 North Kedzie Boulevard, IL, Chicago,
boulevardbikeshop.com
This cozy storefront at the center of Logan Square is one of the few shops in Chicago that offers used bikes, as well as a great selection of commuter bikes and gear.

The Alise Chicago

1 West Washington, IL, Chicago,
www.thealisechicago.com

Formerly the Hotel Burnham, this National Historic Landmark offers access to the Loop's nightlife and business centers, as well as quick access to the Lakefront Trail and Museum Campus.

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The Alise Chicago

1 West Washington, IL, Chicago,
www.thealisechicago.com
Formerly the Hotel Burnham, this National Historic Landmark offers access to the Loop's nightlife and business centers, as well as quick access to the Lakefront Trail and Museum Campus.

Hotel Palomar

505 North State Street, IL, Chicago,
www.hotelpalomar-chicago.com

Offering complimentary bicycles and yoga mats to guests, this classy hotel is located in Chicago's bustling River North neighborhood.

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Hotel Palomar

505 North State Street, IL, Chicago,
www.hotelpalomar-chicago.com
Offering complimentary bicycles and yoga mats to guests, this classy hotel is located in Chicago's bustling River North neighborhood.

Fairmont Chicago

200 N. Columbus Drive, IL, Chicago,
www.fairmont.com

Luxury hotel with available bike rentals, overlooking Millennium Park and the Lakefront Trail

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Fairmont Chicago

200 N. Columbus Drive, IL, Chicago,
www.fairmont.com
Luxury hotel with available bike rentals, overlooking Millennium Park and the Lakefront Trail

Sono Chicago

1428 North Cleveland Avenue, IL, Chicago,
www.thesonochicago.com

Beautiful, refined bed & breakfast in Chicago's historic Old Town neighborhood, with easy access to downtown and the city's north side.

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Sono Chicago

1428 North Cleveland Avenue, IL, Chicago,
www.thesonochicago.com
Beautiful, refined bed & breakfast in Chicago's historic Old Town neighborhood, with easy access to downtown and the city's north side.

Wicker Park Inn

1329 North Wicker Park Avenu, IL, Chicago,
www.wickerparkinn.com

This bed & breakfast nestled in the heart of Chicago's Wicker Park, offers affordable and comfortable rooms in one of Chicago's most vibrant neighborhoods.

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Wicker Park Inn

1329 North Wicker Park Avenu, IL, Chicago,
www.wickerparkinn.com
This bed & breakfast nestled in the heart of Chicago's Wicker Park, offers affordable and comfortable rooms in one of Chicago's most vibrant neighborhoods.
Accordion

Chicago Lakefront Trail

Illinois - 19 miles

The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many...

North Branch Trail

Illinois - 21.3 miles

The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often...

Illinois Prairie Path

Illinois - 58.4 miles

The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main...

Bloomingdale Trail (The 606)

Illinois - 2.7 miles

The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the...

Illinois & Michigan Canal State Trail

Illinois - 79.5 miles

The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. It traverses the I&M Canal National Heritage...

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