Fine dining restaurant · Lincoln Square
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"Michelin-starred restaurant offering a Super Bowl Sunday Party Box for two with brisket, jerk chicken wings, Tasso ham boudin, and more." - Ashok Selvam
American restaurant · Near West Side
Classic diner serving up 3-egg omelets & black coffee (plus lunch & dinner) since 1938.
1 Postcard
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
Clothing store · Uptown
Discover Milk Handmade, a cozy boutique where chic womenswear meets artisanal candles and accessories, all curated with a distinct Chicago flair.
2 Postcards
Museum · Grant Park
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
New American restaurant · Ranch Triangle
Nestled in a breezy beach house vibe, this spot serves up California cuisine and homemade goodies, making it a must-visit for a deliciously laid-back meal.
44 Postcards
Filipino restaurant · Ravenswood
Creative Filipino-Cuban fare & BYOB offered in a snug, artsy setup with outdoor seating.
Mexican restaurant · Pilsen
Hip, low-lit setting for Mexican fare with rustic, art-filled decor & downstairs mezcal bar.
24 Postcards
Mexican restaurant · Sheffield Neighbors
Family-run Mexican eatery showcasing a menu of fresh seafood dishes, including tacos and burritos.
3 Postcards
Seafood restaurant · Gold Coast
Hugo’s is an upscale seafood haven in Chicago, celebrated for its crab cakes, frog legs, and attentive service in a cozy, inviting atmosphere.
10 Postcards
Night club · Near North Side
Energetic nightspot featuring a spacious, neon-heavy bar & an upstairs area for music & dancing.