Art museum · River West
4
Newly renovated in 2025, Intuit centers self‑taught artists—think Henry Darger alongside boundary‑pushing contemporary work. Covered by city arts writers and national outlets, it’s a focused, singular lens on Chicago’s creative history.
American restaurant · Lincoln Park
Great view, American dishes, cocktails, dog-friendly patio
2 Postcards
Chocolate shop · Near North Side
Artisanal chocolatier serving rich hot chocolate, gourmet pastries
3 Postcards
Bar · Lakeview
Vast craft beer selection in a cafe-like space with free WiFi
13 Postcards
Restaurant · West Town
Flavor bomb breakfast sandwiches & smashburgers, creative comfort food
5 Postcards
Vegan restaurant · West Town
Vegan cafe with donuts, burgers, and Italian beef sandwiches
Fine dining restaurant · Lincoln Park
Molecular gastronomy with theatrical presentations and unique flavors
158 Postcards
Bar · Loop
Vast cider selection, live music, and Chicago dogs on the river.
14 Postcards
Pizza restaurant · Goose Island
Tavern-style thin crust pizza, skillet brownie sundae, cocktails
4 Postcards
Coffee shop · Streeterville
Specialty coffees, teas, housemade eats, local baked goods
Bar & grill · Lakeview
Alabama-centric country bar with honky-tonk music & Southern food