Western Avenue is like the Nile of Chicago. The city’s longest continuous road stretches from the North Side boundary at Howard Street to 119th Street on the South Side. (It continues further in the burbs.)
Over the next few months, I’ll be exploring those 24+ miles and bringing you different Western Avenue guides. Today, we begin on Western and Armitage Avenue.
A snapshot of your north-south walk. (Google Maps)
How it Works
- We pick an area within city limits.
- We pick a mile to walk.
- Today: Western between Armitage Avenue and Cortez Street (aka Margie’s to Empty Bottle).
- We recommend ~10 things to do in that mile.
How to Get There
- The Blue Line to Western on the O’Hare Branch at 1900 N. Western Ave.
- Not to be confused with the Western Blue Line on the Forest Park Branch at 430 S. Western Ave.
- Bus No. 49 on Western; No. 56 on Milwaukee; or No. 73 on Armitage Avenue
- Divvy at Western and Winnebago Street
What to Do
The start of this walk is pretty legendary: Margie’s Candies has been on Western and Armitage since 1921, serving up decadent sundaes in addition to the titular candy. (For me, it’s that hot fudge … 🤤)
But if it’s too early for sweets, head across the street to Arturo’s Tacos. Yes, you can go to Arturo’s while the sun is out. The famed night-owl taco joint is (usually) open 24 hours on weekends, the last restaurant standing in its longtime late-night rivalry against the ol’ Lazo’s Tacos.
My Arturo’s go-to: Huevos a la Mexicana. (Emmi Mack / Hey Chicago)
Across the street, there’s a new breakfast option on the scene too: El Bagelero. Their bagels are perfectly chewy, seedy, and light.
Snag a bowling coupon if you’re not into comics. (Emmi Mack / Hey Chicago)
Walk south, and you’ll pass Sweet Rice, which serves street-style Thai in a lively dining room. (Sometimes there are robot waiters 🤖) Go another block and you’ll find Challengers Comics, a colorful, double-storefront comic shop. (Check for upcoming signings here. A “Godzilla” author will visit Aug. 2.)
Dining along the 606 like royalty. (Emmi Mack / Hey Chicago)
Another block and you’ll hit a 606 entrance on Bloomingdale Avenue. Head on up to find Wolf & Company, the city’s first restaurant with direct access to the walkway. On the ground floor, smell their fancy flower bouquets before heading toward North Avenue.
Just a couple doors west of Western, on the south side of North Avenue, is Premium Cigars. (There’s no website, but I’ve got the pics to prove it.) Ask for Mario. He’ll hook it up.
Smoke break! (Emmi Mack / Hey Chicago)
Now keep on trekking toward Cortez. On the way, you’ll pass many dentists, several salons, Roberto Clemente high school, Eerie Division Street Health Center, and Sun Rey Cafe, an unassuming diner with pop-up Filipino specials.
My noble steed at the watering hole. (Emmi Mack / Hey Chicago)
Finally, past Division, you’re in Ukrainian Village … pretty much at Empty Bottle. This reliable rock venue has a solid bar — try their Earth Juice with vodka — and free concerts on Mondays. This Thursday, catch the talented (Chicago native) Grander World Whimsy. And every Friday, there’s honky-tonk! Get Western on Western 🤠
