Milwaukee Avenue & Elston Avenue

Cycle Chicago, Sightseeing Ride, Milwaukee Avenue & Elston Avenue 

This is one of Chicago's gritty urban rides that show how industrial districts in Chicago are developing into residential and shopping areas. Bikes make up a significant part of Milwaukee Avenue’s new identity. Nowhere in the city (except on the Lakefront) will you see more bikes. By one recent count, one-third of passing vehicles at Milwaukee and North avenues during rush hour were bicycles. This stretch of bike heaven offers not only safety in numbers but inspiration for the potential of urban biking.


Flat as a pancake. A hybrid or comfort bike would be best due to all the potholes.


Lots - the most traffic of any ride in Chicago The entire ride is over marked bike lanes, so it does not require much experience riding on Chicago streets. It does, however, require care and attention all along the way.


Take the CTA Blue Line and bike two blocks southeast to start. Several CTA buses will get you there, in particular #56 Milwaukee, #65 Grand and #8 Halsted.

By car, exit Interstate 90/94 at Ohio, turn right on Des Plaines Street and drive three blocks south.

Food and Drink

An enormous number of eateries and drinking establishments.

Side Trips

Tour and shop Wicker Park, a historically important neighborhood. Or tour Revolution Brewing, a new restaurant, microbrewery and bicycle hangout at 2323 N. Milwaukee Ave., opened by the owner of the Handlebar, the city’s heretofore most popular bicycle bar.


More Details

Previously a buffalo path to the Chicago River and then a Native American trail, Milwaukee Avenue has always been a busy thoroughfare. As an angle street, it has provided a shortcut not only for shoppers and workers on their daily rounds but also for ethnic groups on their way out geographically and up economically. Rather than a melting pot, the street has served as a port of entry and witnessed a procession of nationalities, starting with Germans and Scandinavians followed by Poles, Ukrainians, Slovaks and other Slavs, Italians, Eastern European Jews and, most recently, Hispanics.

As a result, this ride passes vestiges of colorful histories. Take your time to shop the goods and sample the foods, from the Little Poland $ Store to storefront taquerias and everything in between. The Poles have dominated the story of Milwaukee Avenue as evidenced along the ride by the Polish American Museum, St. Stanislaus Kostka Church, Copernicus Center and former “Polish Downtown” at Division Street. You’ll also see several important old theaters, including the Gateway, Portage, Logan and Congress.

Today urban pioneers and young people are increasingly salvaging discarded dwellings and rundown streets along this corridor. Former storehouses, corner taverns and automobile repair shops are morphing into wi-fi cafes, upscale restaurants and, yes, boutique bike shops. This transformation is far from complete and may never end, which only underscores the wonderfully dynamic and eclectic nature of this living, open-air museum.

Elston Avenue

In addition to being important for national pride, ethnic community and religious identity, the Milwaukee Avenue corridor has also provided jobs to thousands. That’s why this ride includes a spin along the parallel, nearby Elston Avenue, Milwaukee Avenue’s less attractive cousin. Elston Avenue and Goose Island across the Chicago River have been home to heavy industry, tanneries and freight railroad lines.

Before the Kennedy Expressway ripped through the neighborhood, Elston Avenue was the quickest way to drive downtown, and traffic was heavy. Today, traffic is light and the street holds more potential than promise. Still, some planners believe that bicycle lanes and bicyclists will help bring this street back to life by encouraging development on a human scale in harmony with the light industrial and increasingly residential character of the area.


Ride Log

  • 0.0 Start at Milwaukee Ave and Kinzie St. Buy a bag of Blommer chocolate at the corner to fuel your ride.
  • 0.8 Turn right on Elston Ave.
  • 1.2 Glance behind for a view of skyline, Chicago River and Goose Island, albeit through a chain link fence.
  • 1.3 Note green bike lane to show that bikes going straight through the intersection should ride to the left of cars that are turning right.
  • 1.6 Bear slightly left to stay on Elston Ave. Watch out for railroad tracks.
  • 1.8 Longtime Stanley’s fruit market at North Ave.
  • 2.5 Immediately after Armitage Ave, bear left to stay on Elston Ave. Careful crossing the huge intersection of Elston and Ashland Avenues.
  • 2.6 Kohl’s is the first of several big box stores found on this street. Some of them even have bike racks!
  • 3.1 Careful crossing big intersection of Fullerton, Damen and Elston Avenues.
  • 5.3 Two more big intersections with a lot of traffic, but that will be the end of such busy crossings. Traffic dwindles as you go farther north.
  • 7.6 Turn left on Lawrence Ave.
  • 8.6 Copernicus Center on right.
  • 8.7 Turn left on Milwaukee Ave.
  • 9.8 Portage Theater on right.
  • 9.9 Six Corners, once one of Chicagoland’s busiest shopping areas.
  • 10.7 Carl Schurz Public High School on left. Impressive 1910 building.
  • 12.5 Logan Theater on right.
  • 12.7 Illinois Centennial Monument on right. It marked 100 years as a state.
  • 13.1 Lady Liberty on right.
  • 13.2 Revolution Brewery on left.
  • 13.7 Admire façade of Congress Theater on left. 
  • 14.3 Ride under bridge that will be part of Bloomingdale Trail, a three-mile linear park and bike trail to be built on an elevated former railroad right-of-way.
  • 14.7 Northwest Tower “flatiron” building on right.
  • 14.8 Myopic Books, a great used bookstore, on right.
  • 15.6 “Lovely, a bakeshop” on right. And it is.
  • 15.8 Polish Museum of America on right. Stay to left and beware of cars turning right onto Interstate 90/94.
  • 16.0 That’s a salt dome on left, not futuristic housing.
  • 17.1 End at Blommer Chocolate and buy another bag of chocolate since you probably ate everything you bought at the start.
  • Trail map

    Locate Me
    Get Directions

    26.916 km / 16.725 mi

    Total Distance

    65 m / 213 ft

    Total Ascent

    65 m / 215 ft

    Total Descent

    189 m / 621 ft

    Highest Point

    Ride type:
    Mountain biking
    Road riding
    Kid friendly
    Rail Trail
    Difficulty: Easy (Blue)
    Ride Duration: <1 hr
    Fitness Level: Low
    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: 27.0
    First Aid
    Bike hire
    Bike servicing
    Accessible by bike
    Accessible by car
    Accessible by public transport
    Accessible by shuttle / uber
    Loading comments...