Walk A Mile on Chicago Avenue

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.

How it Works

1. We pick a street within city limits.
2. We pick a mile on that street (Chicago Avenue between Damen and California avenues).
3. 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!

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!