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Chicago Cheatsheet: My Exact Itinerary
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items Stealing My Chicago Itinerary? I Don’t Blame You. 😏
From boutique hotel stays to can’t-miss eats and underrated gems, this curated list covers exactly how I did Chicago—no gatekeeping. Whether you're here for a quick weekend trip or a full-on city e...
Map
Touchdown and check-in made easy! 🚕 After you land, grab an Uber straight to the 21c Museum Hotel—yes, it's a hotel and a legit art museum. When I visited, they were featuring a wild exhibit on reality TV—think real life meets surreal screen moments...
21c Museum Hotel Chicago
If you’re coming from 21c Museum Hotel, you’re basically already there—**Su Casa is just a quick stroll away! 🏃♀️🌮
Don’t let the outside fool you. Inside, it's a total gem: flavorful dishes, strong drinks, and the kind of friendly service that ma...
Su Casa Mexican Restaurant
After your power nap, it’s time for some thrills at 360 Chicago! Get ready to experience Tilt—an adrenaline-pumping ride that quite literally tilts you over the edge of one of the city’s tallest buildings. While you're in line, soak in fascinating st...
360 CHICAGO
Just wrapped up at 360 Chicago? Keep the night going at Moneygun! 🌃🍸 Open until 2AM, this spot is all about good vibes — think chill atmosphere, great music, and seriously tasty bites. Don’t miss the fries (a must with the aioli) and the Briarra ta...
MONEYGUN
After a long night out, you’ll be glued to the bed until hunger finally wins. But don’t sleep too long—you have to make it to Stax Cafe before they close at 3:30 PM. Trust me, it’s some of the best food you’ll ever taste.
Order the Spanish Harlem or...
Stax Cafe - Chicago Breakfast, Lunch, and Brunch Restaurant
If you didn’t take my advice and stay at the 21c Museum Hotel (your loss!), at least do yourself a favor and check out the restaurant inside.
The Lure Bar & Grille is effortlessly cool—seafood-forward, super fresh, and totally worth your time.
Bo...
Lure Fishbar - Chicago
Perched high above the city, Roof on theWit is a rare gem that lives up to the hype. Equal parts sleek lounge, buzzing bar, and high-energy club, this rooftop hotspot is where Chicago nightlife truly shines. Be prepared for a bit of a wait—it’s popul...
ROOF on theWit
After living it up in Chicago - MDW is the way back home. It’s about 20-25 minutes from downtown without traffic. Until next time, I hope these recommendations served you well! Tell me what you enjoyed the most about the trip in the comments!
Chicago Midway International Airport