Western Avenue is the city’s longest continuous road, stretching from Howard to 119th Street — and even further in the burbs. I’m exploring those 24+ miles to offer different Western Avenue guides.
Recently, I bopped around Western and Armitage Avenue.
Today, we’re zooming into the Tri-Taylor Historic District, starting on Western and Madison Street and scooting to Roosevelt Road.
A snapshot of your north-south walk. (Google Maps)
How to Get There
- The Blue Line to Western on the Forest Park Branch at 430 S. Western Ave. Not to be confused with the O’Hare Branch Western Blue Line.
- Bus No. 49 on Western; No. 20 on Madison; or No. 12 on Roosevelt
- Divvy at Western and Madison
What to Do
This journey has a buzzy start: the office of former Ald. Walter Burnett Jr., just a few doors north of Madison.
Burnett represented the 27th Ward for 30 years and recently stepped down. Mayor Brandon Johnson just tapped Burnett’s son, Walter Redmond Burnett, to replace him. City Council must approve the pick.
If “Red” does become the next alder — and keeps dad’s office space — he’ll be right next to Moon’s Sandwich Shop, which has been serving up diner classics for over 90 years. (I love this story of Moon’s.) When I visited Wednesday, the counter was packed. Cooks were churning out delivery orders and singing along to R&B on the radio. My breakfast potatoes were perfectly done.
Moon’s; Raymond’s Tacos; Johnna’s Cafe; the Vietnam Veterans Survivors Memorial; Westside Gyros; Wrap & Roll. (Emmi Mack / Hey Chicago)
A couple blocks south, you’ll hit Raymond’s Tacos. There, I got a massive ground beef taco for $4 and feasted over the expressway at the lovely Claremont Park. On the way, I passed Johnna’s Cafe, which Eater ranks among Chicago’s best soul food restaurants.
After a relaxing lunch in the shade, you might want to recharge at Muse Coffee Studio, a coffee shop full of cozy couches that doubles as an art gallery space. Eclectic paintings cover the exposed brick walls.
Just beyond Muse, we’ll allow ourselves to venture off Western for a few short blocks to the Vietnam Veterans Survivors Memorial on Oakley Boulevard.
I’d never heard of this memorial, which effectively functions as a quiet park. It was cobbled together by Chicago preservationist Bill Lavicka in 1987 to honor fellow, often struggling vets. Today, the tile lettering on the ground is half-rubbed away.
Back on Western, you’ll see West Side City Gyros, its front window a classic collage of Chicago street food, and beyond that, Wrap & Roll, a lively, music-themed sandwich shop.
🛴 Still stuffed, I scootered on home.
