Lounge · Humboldt Park
10
"Stewart’s other regular hangout, The California Clipper, holds 'a magical place' in his heart." - Dillon Mafit
Coffee shop · Noble Square
Counter-service coffeehouse dishing up Filipino-inspired drinks and grub in a relaxed setting.
5 Postcards
Hamburger restaurant · Lakeview
Trendy scene where creative burgers go with fries, housemade sodas, craft cocktails & lots of beers.
11 Postcards
Restaurant · West Loop
Southern dishes & breakfast with a Cajun spin is served in a relaxed setting with spacious patio.
13 Postcards
New American restaurant · Loop
Nestled in a historic 19th-century building, this trendy spot serves hearty American dishes and craft cocktails, ideal for a satisfying outing.
1 Postcard
New American restaurant · West Town
Nestled in a charming setting, Elske serves innovative American dishes with Danish flair, featuring a seasonal menu that delights the palate.
57 Postcards
Museum · Prairie District
Docent-led tours of a landmark 19th-century house & Chicago's oldest building.
Italian restaurant · Near North Side
Savor Neapolitan pizzas, homemade pastas, and a thoughtfully curated wine list in a stylish venue that sets the perfect mood for any occasion.
21 Postcards
Bakery · Garfield Ridge
Bustling, long-running bakery crafting cakes, tortes, donuts & other treats since 1930.
7 Postcards
Pizza restaurant · Wicker Park
Thin-crust pies & house brews in a sports-bar setting with karaoke & live bands some nights.
32 Postcards
American restaurant · Noble Square
Savor game, fresh oysters, and craft brews in a cozy lodge with a fun vibe, where the menu offers a taste of the South you won't forget.
44 Postcards