Chicago is consistently ranked one of the most walkable cities in America, so we’re putting together some one-mile walking guides to help you navigate these busy city streets.
A few stops along Chicago Avenue. (Google Maps)
How it Works
- We pick a street within city limits.
- We pick a mile on that street (Chicago Avenue between Damen and California avenues).
- We recommend ~10 things to do in that mile.
How to Get There
- Divvy at Damen Avenue.
- No. 66 bus at Damen Avenue.
- No. 50 bus at Damen Avenue.
Ready, set, walk!
What to Do
Start at Mariano’s and head to the rooftop parking lot for a free panoramic view of the skyline. Then get a deli sandwich from Kasia’s Deli!
Head into All Together Now for a glass of wine and a charcuterie tray. Peep their free postcard and their wine fridge for a fun gift!
Pick up vintage clothes and furniture at Able Shoppe, aka the former Stoop storefront. For a taste of Ukrainian heritage, Delta M has traditional clothes, home goods, and books in the language.
Make a pit stop at Star Lounge Coffee Bar for Dark Matter coffee, espresso, or an horchata latte 💗 Then, stop at Komoda to shop some of the best apothecary options in the area!
The No. 66 bus on Chicago Avenue. (Caroline Patton / City Cast Chicago)
Heritage Restaurant & Caviar Bar has one of the best happy hours in the city! Going there for dinner? They have a revolving menu. Pro tip: They have a special menu running through the end of August for their birthday month. 🎂
End the night at Continental Lounge, one of Chicago's 4 a.m. bars! Their photo booth has great lighting, the back patio is private and open until midnight, and Chicago handshakes are on the menu as you'd expect from a true Chicago dive bar!
