Hotel · Loop
13
"The Kimpton Gray Hotel in Chicago is set in a historic building and features the rooftop restaurant Boleo, offering Peruvian street food-inspired cuisine."
Jazz club · Near North Side
Nestled in River North, Andy's Jazz Club offers an intimate setting for live jazz, where the music reigns supreme—dinner is secondary, but the vibes are top-notch.
4 Postcards
Stadium · Bridgeport
Guaranteed Rate Field, home to the White Sox, boasts an impressive array of food options and a lively atmosphere, making it a must-visit for baseball fans.
10 Postcards
Indian restaurant · Near North Side
Vermilion is a chic, modern spot in River North that's recently transformed into an exciting Indo-Chinese fusion gem, featuring bold flavors and creative dishes.
13 Postcards
Restaurant · Logan Square
Beautiful Rind is Logan Square's cheese-lovers haven, boasting a vibrant selection of artisanal cheeses, charcuterie, and a cozy atmosphere for dining and tasting classes.
8 Postcards
Diner · Tri-taylor
Hip, bright setting with retro diner references offering American breakfast & lunch fare & coffee.
3 Postcards
Restaurant · West Town
Recess in the West Loop is a sprawling, vibrant playground for adults, featuring a massive patio with games, creative cocktails, and a lively atmosphere perfect for any celebration.
32 Postcards
Halal restaurant · Near North Side
The Halal Guys brings its famed late-night Middle Eastern fare to Chicago with hearty gyros and falafel options, perfect for a quick, satisfying takeout meal.
American restaurant · Loop
Nestled across from Millennium Park, this bi-level pub serves elevated comfort food and craft cocktails, boasting cozy vibes and great skyline views.
2 Postcards
American restaurant · Near North Side
JoJo’s Shake Bar is a whimsical dessert haven in River North, serving up over-the-top milkshakes and playful bites in a vibrant, nostalgic atmosphere.
15 Postcards
Mexican restaurant · West Town
Dive into authentic Poblano delights, from hearty cemitas to flavorful tacos, in a no-frills spot that's all about big taste and fresh ingredients.