Choose Chicago on Instagram: "Valentine’s Day is this Saturday, and if you’re planning something sweet, Chicago's Black-owned dessert shops are READY. 🧁 Think decadent cakes, ice cream sundaes, handmade chocolates, brownies, cookies and treats that feel like love at first bite. Perfect for date night, Galentine’s, or just treating yourself. FUN FACT: One of the desserts in this video is called “The D. Rose,” named after Derrick Rose’s favorite treat and in honor of his retirement. Can you guess
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Choose Chicago on Instagram: "Lincoln Square in the fall feels just like Stars Hollow. 🍁 Cute shops, colorful leaves, and that cozy small-town charm make it feel like you’re in a Gilmore Girls episode. Share this with someone who’d love to pretend they’re in Stars Hollow! 🎥: @chicagoismyboyfriend #NeverOutdoneChi"
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Choose Chicago on Instagram: "Pack your month with FREE things to do in Chicago! ✨ So many affordable can't-miss holiday activities coming up in November. 🔗 Tap our link in bio for 10 free things to do in November #NeverOutdoneChi"
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Choose Chicago on Instagram: "ANOTHER WIN 🏆 Less than a month after being named the Best Big City in the U.S. for the 9th year straight by @cntraveler readers, Chicago was named one of Frommer’s “Best Places to Go in 2026." Chicago joins global destinations like Vienna, Adelaide, Fiji, and Patagonia Azul in Argentina on this prestigious list by @frommers. Chicago is having a moment and we have no plans of letting up. We saw a record-breaking summer with more hotel rooms filled than ever and the
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Choose Chicago | THIS JUST IN 🤩 The 2026 dates for the @Chicagodcase festivals and events are HERE! From beloved staples like the Chicago Blues Festival... | Instagram
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Choose Chicago on Instagram: "Chicago during the holidays? NOTHING. COMES. CLOSE. ❄️✨ There’s just something about the city this time of year. Everything feels extra cozy. Twinkly lights everywhere. Ice skating with that skyline view. Festive markets and holiday shows all around. It’s all just magical. It’s one of those seasons that makes you slow down for a second and soak it all in. 🔗 Tap the link in bio to see top things to do and see for the holidays. #NeverOutdoneChi"
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Choose Chicago on Instagram: "Looking for a Chicago experience you’ll never forget? 🌃🍕 Enjoy some of the most incredible, panoramic views in the city during a private, after-hours visit to SkyDeck Chicago @skydeckchicago. With Pie in the Sky, you get rare access to the 99th or 103rd floor along with a 3-course Giordano’s meal featuring their legendary deep dish. It’s a bucket-list experience and a seriously great holiday gift idea too. 👉 FYI: Reservations are required at least 3 business days
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