Puerto Rican restaurant · Irving Park
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"A new board games cafe serving Puerto Rican cuisine, coffee, cocktails, and beer is open at 3932 W. Irving Park Road with more than 500 games to choose from." - Naomi Waxman
Cocktail bar · Uptown
This iconic jazz club dishes out nightly live sounds, from renowned acts to spontaneous jams, all in a lively, character-filled atmosphere.
18 Postcards
Art museum · Streeterville
This downtown museum is a cozy haven for post-WWII art lovers, featuring immersive exhibits, a scavenger hunt for kids, and a charming gift shop.
11 Postcards
Hot dog stand · Norwood Park East
Step back in time at this charming 1948 drive-in where you can savor Chicago-style hot dogs, crispy fries, and rich milkshakes—all from your car.
29 Postcards
Spanish restaurant · South Loop
Nestled above Grant Park, Mercat a la Planxa serves up inventive Catalan tapas and cocktails in a chic space, perfect for leisure or special occasions.
10 Postcards
Steak house · Loop
Industrial-chic steakhouse offering an extensive menu of specialty steaks, plus seafood.
Korean grocery store · Avondale
This vibrant Asian market offers fresh produce, meats, and dry goods alongside a cozy Korean eatery serving up delightful dishes like kimchi pork buns and spicy soups.
12 Postcards
Chinese restaurant · South Loop
Casual eatery specializing in Chinese dishes, including spicy boiled beef and pickled fish.
9 Postcards
Steak house · Streeterville
Long-standing steakhouse serving slow-smoked American barbecue like its signature babyback ribs.
6 Postcards
Coffee shop · Wicker Park
Step into the Wormhole, where an 80s nostalgia fest meets great coffee, complete with a DeLorean, vintage decor, and a vibey, communal atmosphere.
American restaurant · Loop
Savor refined cuisine and creative cocktails in a vibrant setting with Millennium Park views that perfectly balances casual charm and culinary delight.
22 Postcards