Biking in Chicago, America’s Leading Bicycle City

In 2016, Bicycling Magazine named Chicago #1 of America’s Best Bike Cities (Cambridge was #8 and Boston #17). On a recent visit, my wife Ann Marie and I set out to see what set Chicago at the top when it came to bicycling. 



We found that bicyclists in Chicago rely on a combined network of dedicated trails and on-street bike lanes to get around the city. Dedicated bike and walking trails run along many bodies of water, including the Lakefront, the Riverwalk, the 606/Bloomingdale Trail, and the Calumet-SagCanal. Miles of on-street bike lanes, many of them buffered from motor traffic create connections downtown and elsewhere.


Chicago's Lakefront Trail (Photo: PBIC Images)

The 19-mile Lakefront Trail was a real standout in our book. It traces the Lake Michigan shoreline that Daniel Burnham called for preserving as green space in the famous 1909 Chicago City Plan. Riding in the shadow of Chicago’s magnificent skyline along the vast GreatLake was a thrilling urban experience. The Lakefront Trail has been connected by new bike and pedestrian bridges across the Lakeshore Drive highway and railroad tracks to several neighborhoods. We explored the lakefront on bicycles rented from the Divvy bikeshare system (established 2013), With more than 580 stations, it is the second largest bike share in North America, after New York.

Another engaging ride was on the 606/Bloomingdale Line (2013), a 2.7-mile refurbished raised rail line that resembles New York’s High Line. The 606, which was designed by Cambridge landscape architect Michael Van Valkenburgh, accommodates bikes well, since it’s wider and straighter than the High Line. With a dozen access points, it links several neighborhoods in Northwest Chicago.

Outside the urban core, there are notable greenways in Chicagoland. Some trails pass through the Forest Preserves that Daniel Burnham advocated for over a century ago. The longest Forest Preserve trail (56 miles) passes along the Des Plaines River, to the west of the city. One of the most ambitious greenways is the Calumet-Sag Trail (2015), which parallels the Calumet-Sag Channel. The Channel carried barges through the heavy industry heartland of South Chicago for most of the 20th century. About half of the projected 26 miles of the Calumet-Sag Trail have been completed. The banks of the industrial channel have grown over with trees, natural grasses, and wildflowers, making it a bucolic ride. Bikers and hikers can access five other multi-use recreational trails from the Calumet-Sag Trail.

The Chicago River, with its North and South Branches, has great potential as a greenway. The recently opened 1.3-mile Riverwalk (2016, designed partly by Watertown’s Sasaki), runs through the heart of downtown, but intensive pedestrian use makes it less than optimal for bicycle travel. The North Branch of the Chicago River has almost 15 miles of bike trails, but they do not connect with the Riverwalk, and the South Branch has virtually no bike trails in place. The City and non-profit Active Transportation Alliance (Active Trans) have announced collaborative initiatives for building a complete system of trails along both branches of the Chicago River.


 Bicyclists in downtown Chicago. (Photo: Alyson West via PBIC Images)

The dedicated bike and walking trails, which follow protected green spaces and waterways, are not sufficient on their own to make Chicago a first-rate biking city. They don’t easily connect with each other and the city’s neighborhoods. Most of the city is laid out on a fully developed urban grid, which lacks natural greenways. Although the grid does not allow for easy bikeway development, it provides wide, flat avenues that can accommodate designated bike lanes.

During my stay in Chicago I met with Diane Banta, the National Park Service Rivers, Trail & Conservation Assistance coordinator for the city. She helped to explain how Chicago has become the bike-and-walking-trail leader, by pointing out that Mayors Daley and Emanuel have maintained the vision that Chicago should be the foremost biking city in America and have backed it up with substantial infrastructure funding. The creation of Chicago’s expansive bike and walkway network has been abetted by the fact that the city’s municipal boundaries encompass an area four times larger than Boston, which has eased the challenges of jurisdictional coordination. Chicago’s initiatives have been further animated by the WindyCity’s ambitious, can-do spirit. When Daniel Burnham issued the challenge to “make no little plans,” he knew he was setting the bar high for future leaders.


 Bicyclists wait in a bike box at an intersection in Chicago. (Photo: Alyson West via PBIC Images)

In the 1990s, Mayor Richard M. Daley started the ambitious bike-lane construction program. Today, under current Mayor Rahm Emanuel, Chicago has more than 160 miles of protected or buffered bike lanes. Like most cities, Chicago’s protected bike network is not continuous, so riders can be suddenly jettisoned into heavy motor traffic and hazardous big-city intersections. Although the city has almost 130 bike lanes and marked shared lanes, these are not adequate to make many cyclists feel comfortable. City government, guided by the Streets for Cycling Plan 2020, recognizes this as a problem and is working to stitch together a continuous network of 645 miles of bikeways throughout Chicago. The overall system consists of three route types: “Neighborhood Bike Routes” that utilize residential streets, “Crosstown Bike Routes” that use collector and arterial roadways, and “Spoke Routes” that connect all corners of the city to downtown on protected bikeways.


A bicyclist in Chicago. (Photo: Alyson West via PBIC Images) 

Active Trans is also advocating for protected bikeway initiatives because of the necessity of providing “low-stress bikeways” that can attract a wider ridership across the city. Active Trans is comparable to Boston’s LivableStreets Alliance, promoting Complete Streets and Vision Zero initiatives, as well as biking, walking, and transit. 

The big takeaway for Boston and its efforts to build out an Emerald Network of bike and walking trails is that Chicago has been successful because of political commitment from its mayors. The Emerald Network needs solid financial commitments from Boston’s Mayor Walsh, but from mayors in surrounding communities as well. Because of the critical role played by the State Department of Conservation and Recreation in maintaining the metropolitan parks and parkways, Governor Baker and the legislature must have skin in the game.