Shoe store · Bucktown
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"Tom's Shoes, Wicker Park. Tom's shoes in real life! This store not only sells shoes, but coffee too! The vibe inside is super laid back and friendly. Chat up one of the employees to learn about where the money goes for each product made."
New American restaurant · West Town
At Eleven Eleven, a stylish West Loop spot, indulge in an eclectic menu blending New American dishes with global inspirations, all in a relaxed yet upscale vibe perfect for cocktails or cozy dinners.
18 Postcards
Bar · Old Town
Nestled near Second City, Old Town Ale House is a legendary dive famous for its eclectic art, vibrant jukebox, and laid-back charm, attracting locals and comedians alike.
16 Postcards
Bar · Wicker Park
Wynwood Kitchen and Spirits is a vibrant, graffiti-adorned hub serving creative American dishes and inventive draft cocktails in a lively atmosphere, complete with a charming patio.
2 Postcards
Hotel · Streeterville
Nestled on the iconic Magnificent Mile, The Drake Hotel exudes vintage Chicago charm with elegant décor, sumptuous rooms, and a renowned afternoon tea service.
4 Postcards
Restaurant · Ashburn
Nestled in Ashburn, Jerk Soule offers a cozy takeout experience of flavorful Jamaican and soulful dishes, with highlights like tender jerk chicken and delicious sides that feel like home.
Sandwich shop · Logan Square
Substantial sandwiches, wraps & snacks served in a laid-back restaurant with a patio.
Brewery · North Center
This cozy microbrewery serves up a stellar selection of craft beers alongside friendly vibes, perfect for grabbing a drink or a game with pals.
13 Postcards
Coffee shop · Gold Coast
Hotel-based French cafe & patisserie offering savory items and house-baked pastries with coffee.
10 Postcards
Hostel · Loop
Nestled in Chicago's vibrant Loop, this modern hostel combines affordability with comfort, offering trendy dorms, cozy private rooms, and a lively atmosphere just a stone's throw from iconic attractions.
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Restaurant · Wicker Park
Casual-chic spot for French seafood & raw bar with coastal wines & 1920s-inspired cocktails.