Hotel · Loop
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"The Kimpton Gray Hotel in Chicago is set in a historic building and features the rooftop restaurant Boleo, offering Peruvian street food-inspired cuisine."
Restaurant · West Town
Maxwells Trading is a bustling West Loop eatery where fusion dishes like bruleed Japanese sweet potato and inventive dips reign supreme, all served in a vibrant, spacious setting filled with great vibes and curated cocktails.
24 Postcards
Chinese restaurant · New Eastside
MingHin Cuisine offers a vibrant twist on traditional Cantonese dim sum and seafood favorites in a spacious, modern setting near Millennium Park, where quality meets fun dining for families and friends.
7 Postcards
Coffee shop · Bridgeport
Jackalope Coffee & Tea is a quirky Bridgeport gem with a vibrant decor, serving up strong coffee, tasty pastries, and a cozy vibe perfect for hanging out.
3 Postcards
Bakery · Wicker Park
In the heart of Wicker Park, Alliance Bakery offers a whimsical assortment of artsy cupcakes, elegant cakes, and exquisite European pastries, all perfect for indulging in at their charming outdoor café.
Sandwich shop · Little Italy
Carm's is a beloved corner eatery in Little Italy serving up classic Chicago fare like Italian beef, hot dogs, and homemade Italian ice with a family touch since 1929.
4 Postcards
Restaurant · Lakeview
Family-focused option for refined American comfort foods plus brunch, full bar & happy hour.
11 Postcards
Cocktail bar · Wicker Park
Hidden behind a graffiti-covered wall, this cozy cocktail lounge offers expertly crafted drinks, small bites, and a relaxed speakeasy vibe perfect for any night out.
41 Postcards
Italian restaurant · Heart of Chicago
Bacchanalia, a cozy family-run Italian eatery since 1979, dishes up hearty classics like lasagna and chicken vesuvio, with a charming, old-school vibe that feels like dining at your favorite aunt's house.
2 Postcards
Bar · East Pilsen
Step into Pilsen's Skylark, a cash-only dive bar with a retro vibe, where craft beer flows, pub food hits the spot, and the local music scene thrives.
French restaurant · Near North Side
American dishes in a high-end dining room with city views on the 16th floor of Trump Hotel & Tower.
13 Postcards