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."
New American restaurant · River North
Stylish and unpretentious, this spot serves creative modern American dishes alongside inventive cocktails, all in an inviting atmosphere.
24 Postcards
Hamburger restaurant · Humboldt Park
Bianca’s Burgers is a cozy, family-owned gem in Chicago crafting mouthwatering burgers and more, all served with top-notch, friendly service.
4 Postcards
Chinese restaurant · Near North Side
Nestled in the opulent Peninsula Hotel, Shanghai Terrace serves upscale Chinese fare beneath glamorous '30s decor and downtown skyline views, making it ideal for a memorable dining experience.
13 Postcards
New American restaurant · Andersonville
Little Bad Wolf in Andersonville serves up a cozy vibe with killer burgers, an extensive whiskey and beer list, and inventive comfort food that's perfect for any night out.
22 Postcards
Sushi restaurant · Near North Side
Sushi-san is a vibrant River North venue where high-quality sushi meets a lively atmosphere, complete with hip hop tunes and a fun twist on Japanese classics.
40 Postcards
Cocktail bar · Near North Side
Step into the hidden paradise of Three Dots and a Dash, a trendy tiki bar where tropical cocktails and retro decor whisk you away from Chicago's winter chill.
26 Postcards
New American restaurant · West Town
Roister, the laid-back gem of the Alinea Group, serves up inventive New American comfort food amidst a bustling, open-kitchen vibe.
30 Postcards
Bakery · Park Manor
Brown Sugar Bakery is a charming Chicago bakeshop renowned for its decadent Southern-style treats, especially its beloved caramel cake that keeps locals coming back for more.
18 Postcards
American restaurant · Logan Square
Longman & Eagle is a Logan Square gem blending hipster vibes with creative farm-to-table dishes, hearty whiskey selections, and a cozy inn upstairs.
44 Postcards
Pastry shop · Sheffield Neighbors
Located in Lincoln Park, Floriole Cafe & Bakery is a sun-soaked haven for pastry lovers, serving up irresistible European-inspired treats and hearty sandwiches in a chic, airy space.