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.
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.
Chicago Lakefront Trail
The Bloomingdale Trail, or "The 606."
A view of Chicago's skyline from the beach.
A view from one of Chicago's Skyscrapers.
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.
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.
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.
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.
Check out these helpful websites for planning your travel in Chicago.
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...
This great little BYOB sushi & robata grill in West Town calls itself "Japanese Inspired", taking some delicious creative liberties with traditional cuisine.
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...
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...
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!
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...
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.
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.
Consistently one of the best-curated and most progressive bookstores in Chicago, hosting readings, book groups, and kids' storytime.
This staple of Wicker Park houses galleries, theater spaces, and artists' lofts, with regular shows and open houses.
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.
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...
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.
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.
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.
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.
Offering complimentary bicycles and yoga mats to guests, this classy hotel is located in Chicago's bustling River North neighborhood.
Luxury hotel with available bike rentals, overlooking Millennium Park and the Lakefront Trail
Beautiful, refined bed & breakfast in Chicago's historic Old Town neighborhood, with easy access to downtown and the city's north side.
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.
Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake...
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The northern section of the Tinley Creek Trail is a series of color-coded connected loops and spurs that weave through several forest preserves in...
Closure Notice: The trail is closed at the 127th Street bridge until the end of 2024. Overview The Cal-Sag Trail (also known as the Calumet-Sag...
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...
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...
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...
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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...
The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. It traverses the I&M Canal National Heritage...
At first glance, the bright lights of Broadway with traffic signals at every block may not seem like an ideal place for biking and walking, but New York City is full of surprises. Trails have been carved out for cyclists and pedestrians across all five boroughs, in parks, lining the riverfront, in nature preserves, on former elevated rail lines and alongside the beaches (yes, New York City has...
The doorways to San Francisco are always open. Visitors can arrive by car, public transit, ferry or bike. Its position at the waterfront, characteristic hills, compact streets and unique districts lead to the city being very congested, yet very walkable. The established trail network leading to and along key destinations such as the Golden Gate Bridge, Golden Gate Park and the Presidio sits...
For its small size, the nation’s capital is jam-packed with attractions: world-class museums, a plethora of historical sites, top-notch theaters and art galleries and a first-hand look at America’s three branches of government. And, for those who want to take it all in, an expanding network of bicycling and walking facilities connects it all.
Despite the hills, despite the rain, Seattle is a great city for walking and biking. And, thanks to the city’s infrastructure investments, it’s slowly getting better all the time. In 2016, Bicycling Magazine ranked Seattle the 5th best bike city in the U.S. WalkScore says Seattle is the 8th most walkable city in the country.
The Magic City is a multicultural destination with water, water, everywhere. The greater Miami metropolitan area stretches from the Everglades, the famed River of Grass, in the west to the Atlantic Ocean in the east, so the city’s trails cover a variety of landscapes and settings. From protected natural areas and sandy beaches to historical neighborhoods and urban hot spots, there’s something for...
Whether you prefer pedaling among high-rise buildings of downtown, clocking fast miles on a paved veloway, exploring a gravel trail along the lake or cruising separated bike paths alongside creeks and streams, Austin’s trail system beckons. The city may be best known for its network of single-track mountain biking and off-road running trails along Barton Creek, but it’s quickly making strides with...
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.
Water, most notably the Mississippi River, but also Minnehaha Creek and the Chain of Lakes, shaped the Twin Cities of Minneapolis and Saint Paul, literally. The river, creeks and lakes provide the defining beauty and character of the landscape. They also attracted people, supported the industries the led to the growth of the cities and encourage the active lifestyle of today’s citizens.
Towering saguaros, 115-degree summer temperatures, Major League Baseball spring-training parks: They are all signature features of Phoenix, Arizona. A bit more under the radar, perhaps, is the well-established network of trails that crisscrosses the massive urban area.
Picture year-round mild weather, miles of multi-purpose trails, one-of-a-kind sights and a mountains-to-coast terrain with small hills, short hills, large hills and long hills—all interspersed with acres of level land. If you see a pattern here—best described “perfect”—you’ve captured San Diego County’s biking and hiking scene.
