Maggie Daley Park Ice Skating Ribbon

This vibrant Pilsen gem offers an irresistible array of Mexican ice cream and paletas, where colorful flavors and friendly vibes create a sweet escape.

Lou Malnati’s serves classic Chicago deep-dish with a flaky, buttery crust, rich tomato sauce, and gooey cheese in a cozy, family-run setting.

Magnolia Bakery charms with fresh-baked cupcakes, iconic banana pudding, and buttery cakes served in a Tiffany-blue cozy spot.

SPIN Chicago is a vibrant, multi-level ping-pong social club where you can enjoy global bites, specialty cocktails, and non-stop fun amidst a lively atmosphere.

Nestled in Roscoe Village, this cozy bakery serves up dreamy whole-grain croissants and unique pastries, all paired perfectly with coffee and espresso.

Sifr is a stylish new spot in River North where you can savor vibrant Middle Eastern dishes and cocktails, all enjoyed from a trendy rooftop.

Kayao is a chic little gem in Old Town serving vibrant Peruvian-Japanese dishes like fresh ceviche and perfectly cooked seafood, all against a lively backdrop of cocktails and clubby beats.

The Publican in Fulton Market serves hearty farm-to-table pork, seafood, and veggie dishes in a lively, communal beer hall setting.

Spiaggia, a Michelin-starred Italian gem, has offered elevated dining and breathtaking views on Michigan Avenue for over three decades, celebrating artistry and flavors that have charmed everyone from the Obamas to top chefs.

Boleo, perched atop the Kimpton Gray Hotel, is a lively South American rooftop restaurant with a retractable glass roof, offering vibrant cocktails and a festive atmosphere perfect for both casual hangouts and special occasions.