Biking the Boulevards

Cycle Chicago, Road Ride, Biking the Boulevards

This is a challenging yet extremely enjoyable ride. The challenging part is dealing with traffic because about half of the ride is on city streets that don’t have bike lanes, although they are designated as bike routes. Some of these streets have heavy traffic, so the best time to take this ride would be on the weekend. The enjoyable part is seeing scores of parks, statues, historical sites, landscaping gems and architectural wonders along the way.

Our ride starts at the Monument to the Great Northern Migration and ends near the Illinois Centennial Monument in Logan Square. Between these two monuments you’ll see the Rainbow/PUSH headquarters, the Center for Green Technology and the infamous Cook County Jail. You’ll bike by the former homes of an incredible cast of characters, from Ida B. Wells to the Marx Brothers. And you’ll see Chicago’s oldest “L” station at Garfield on the CTA’s Green Line as well as the Fountain of Time, a provocative sculpture by Lorado Taft. Yes, this ride really packs it in!

The parks connected by the boulevards are remarkable themselves. Washington Park was designed by Frederick Law Olmsted, who also designed Central Park in New York City. Douglas Park was laid out by William Le Baron Jenney, considered to be the father of the skyscraper. Sherman Park’s fieldhouse was designed by Daniel Burnham and is one of the first fieldhouses in the world. Garfield Park’s fieldhouse has a gold dome. And from 1928 to 1946, Humboldt Park sported a popular velodrome that was used for six-day races, among other things.

The 28-mile Boulevard System is one way Chicago has tried to live up to its motto, Urbs in Horto, which was adopted in 1837 and means “city in a garden.” The system was envisioned as a crescent with each tip connecting to the lake, but the northern leg along Diversey Parkway was never built. Nevertheless, the Boulevard System is a great asset to the city. WTTW Channel 11 and Geoffrey Baer rightly selected it as one of Chicago’s most important features. And the Boulevard Lakefront Tour has long been one of the Active Transportation Alliance’s most popular annual rides. Come see why.



Some quiet roads through city parks but mostly city streets with a number of cars and potholes.


Despite some traffic congestion, most of this ride is along pleasant streets. About half of these streets have designated bike lanes; the others have “bike route” signs.


Take the CTA Red Line to Chinatown; bike four blocks south and four blocks east to the start.

By car, exit Lake Shore Drive at 31st Street and drive west to Martin Luther King Jr. Drive. Turn right and drive to 26th Street. On-street parking is available in the area.

Food and Drink

Innumerable restaurants and convenience stores along the way, in particular in Logan Square near the finish.

Side Trip

There are so many options! Visit one of Chicago’s most overlooked museums, the DuSable Museum of African-American History, four miles into the ride. Also right along the way is the beautiful Garfield Park Conservatory 19 miles in. Once given up for dead, the building was renovated in the 1990s. Today the conservatory is one of the city’s most lively, attractive flower and horticultural centers.


Ride Log

  • 0.0 Start at 26th St and Martin Luther King Jr. Dr at the Monument to the Great Northern Migration. Bike south.
  • 1.4 Bear left on King Dr, biking on the wide middle street, not the side road.
  • 2.6 Turn left on 47th St.
  • 3.1 Turn right on Drexel Blvd (first street after Cottage Grove Ave).
  • 3.8 Bike through intersection with 51st St and ride past fountain as you turn right onto Payne Dr.
  • 3.9 Follow Payne Dr left as it curves south.
  • 4.5 Pass Garfield Blvd, which intersects from the left. A short distance later, bear left at Y to stay on Payne Dr.
  • 5.0 Turn right on Midway Plaisance, which becomes Russell Dr in the park.
  • 5.4 Follow Russell Dr right as it curves north.
  • 6.0 Turn left at T onto Morgan Dr.
  • 6.1 Turn left onto Garfield Blvd, but watch out for traffic that continues north on Morgan Dr.
  • 6.7 Traffic gets busy as you approach CTA’s Red Line.
  • 8.3 Turn right on Throop St and then right again on Sherman Dr to loop around park.
  • 9.2 Turn right on Garfield Blvd. 10.6 Turn right on Western Ave.
  • 13.2 After crossing 35th St, bear right at Y following sign to stay on Western Ave. (Don’t take bridge on left.)
  • 13.6 Turn left on 31st Blvd.
  • 14.0 Turn right on California Blvd.
  • 14.9 Turn left on 24th St.
  • 15.1 Turn right on Marshall Blvd.
  • 15.7 Turn left at T to follow Sacramento Dr through park.
  • 15.9 Cross Ogden Ave.
  • 16.2 Turn left on Douglas Blvd.
  • 17.0 Turn right on Independence Blvd.
  • 18.1 Turn right on Jackson Blvd into park.
  • 18.2 Turn left on Central Park.
  • 19.3 Turn right on Franklin Blvd.
  • 20.1 Turn left on Sacramento Blvd, which becomes Humboldt Blvd in the park.
  • 22.2 Turn left on Palmer St at north side of Palmer Square.
  • 22.5 Turn right on Kedzie Blvd.
  • 23.0 Turn right on Logan Blvd but stay right on the safer side street.
  • 24.0 End ride before going under Kennedy Expressway. The boulevard system continues to Diversey Parkway, but it’s not worth crossing Western Ave for the few extra feet. To get back to the start, take the CTA Blue Line from Logan Square and transfer to the Red Line for Chinatown, or bike back via Milwaukee Avenue, Des Plaines Street, Roosevelt Road, Michigan Avenue and 26th Street.
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    38.213 km / 23.744 mi

    Total Distance

    88 m / 288 ft

    Total Ascent

    89 m / 291 ft

    Total Descent

    186 m / 609 ft

    Highest Point

    Ride type:
    Mountain biking
    Road riding
    Kid friendly
    Rail Trail
    Difficulty: Intermediate (Red)
    Ride Duration: 1-2 hrs
    Fitness Level: Medium
    Shared Bike Path - Paved
    Shared Bike Path - Dirt
    On-Road Bike Lane
    Off-Road - Fire Trail
    Off-Road - Rail Trail
    Off-Road - Single Track
    Off-Road - Downhill
    Mobile Coverage: Excellent
    Estimated Distance: 38.0
    First Aid
    Bike hire
    Bike servicing
    Accessible by bike
    Accessible by car
    Accessible by public transport
    Accessible by shuttle / uber

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