Weekend Wheeling in Chicago
A diagonal ride through Chicago's strict grid-lined streets is a great time-saver that makes cycle-commuting easier. The one big drawback is the six-way intersection. You'll encounter more than a few of these traffic-confounding nightmares along the way, but the snarl is a lot harder on cars than on bikes.
Milwaukee Avenue is one of the handful of diagonal thoroughfares that cut across Chicago's rectilinear streetscape. Once the road that connected 19th-century Chicago with Milwaukee, Milwaukee Avenue is now a colorful boulevard of restaurants and retail shops. As it slices across Chicago's Northwest Side, it is the magnet that attracts the diverse population making up the area's patchwork of ethnic communities.
The trip begins at the forest preserve entrance at Devon Avenue and Milwaukee Avenue on the far northwest side of the city. Check your tires for air and your bottles for water because it is a 10-mile ride to the heart of the city, with many more places to ride once you get there. Saddle up and head southeast.
Only a quarter-mile into your trip, you are faced with your first decision of the ride. Elston Avenue splits off from Milwaukee. Elston is also a diagonal street, running parallel to Milwaukee. It is a not-so-scenic industrial corridor, but it has a designated bicycle lane that encourages fast riding. Milwaukee Avenue, on the other hand, is a crowded melting pot of ethnic storefronts, schools, and churches. At the cost of missing out on some interesting cultural sights, you can ride Elston Avenue and may get to the city faster and more safely.
After a few miles, Milwaukee Avenue's neighborhoods change hands from Polish to Latin. Tavern signs change from "Zimne Pivo" to "Cerveca Fria," the food gets a lot hotter, and insurance agencies once offering "ubezpieczenia" sell "suguros" instead. Chicago's neighborhoods patch together many ethnic varieties, and Milwaukee Avenue sees many of them.
Five or six miles into your ride, you'll get your first leather pants sighting and know that you have entered Wicker Park, one of Chicago's artistic enclaves. Wicker Park was recently snatched from its starving-artist community by the urban gentry. The artists before them moved out the Mexican-Americans, who themselves settled within the Polish American community, which 100 years ago pushed out the urban gentry. Throughout the years, the flavor has changed, but the rows of Victorian mansions and homey bungalows have remained the same.
By the time you reach Ashland Avenue, Chicago's beautiful skyline will open up. Just a little farther, you zoom past coffee shops, outsider art galleries, and nightclubs with four o'clock licenses.
Milwaukee Avenue ends at the intersection of Kinzie and Halsted. A sip of water, a stretch of your quads and calves, and you are ready for a self-guided tour of downtown Chicago, with many museums, shops, and architectural wonders to amaze you.
The Return Trip
On your return trip, find Milwaukee Avenue and head back northwest. After logging many urban miles, maybe that bicycle lane on Elston Avenue won't seem so bad. You can pick up Elston just north of Chicago Avenue as it veers off to the right.
Most of Elston is commercial and industrial, but some shades of local color pop up between the factories in short strips of housing and small restaurants. Life along this gritty corridor can be hard, but many of the homeowners refuse to give in, tending to overgrown flower gardens, repainting their houses, and sweeping the sidewalks every morning. One desperate plea for sanity, hand lettered on a freshly painted wall reads, "Madre de Dios, No Mas Grafitti!"
With few glimpses of humanity to distract you, the miles fly and Elston rejoins Milwaukee Avenue at Melvina Avenue. From here, you're within sight of Superdawg and your journey is nearly over. You may have covered 22 miles of road (and however many miles you have pedaled exploring the downtown area), but you've only seen a fraction of the city.
Details mentioned in this article were accurate at the time of publication