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Hotels in Chicago

Book Cheap Last-Minute Hotels in Chicago

You book your last-minute hotel deals in Chicago, pack your deep-dish-pizza-eatin’-pants, you blow into the Windy City…now what? You buckle in for a Chicago-style good time, that’s what.

When you first emerge from the Chicago hotel deals you scored, you have to give all the quintessential things a Chica-GO: Take the river and lake cruises, selfie at the Bean until you run out of storage, do all the big sports things, and museum it up. But there’s so much more you should give a whirl to experience in the best of the Midwest.

C’mon Feel the Illinois

View from the Top: What’s the ultimate way to see everything in Chicago? Simple—get a bird’s eye view. Get walking and see the city from the 606, an elevated trail and park that’s nearly 3 miles long. Or check out Chicago from the greatest of heights at the 360 Observation Deck, which is 94 stories up, and hosts yoga on Saturday mornings for only the bravest souls. The Ledge at Skydeck is another soaring option, consisting of a clear glass box that’s over 1,300 feet off the ground. Scaredy cats need not apply.

Team Alternates: Yeah, Chicago is a big ol’ sports town, but what about other, less mainstream options? Think there’s no “I” in team? WhirlyBall is a combo team sport of jai alai and basketball played on bumper cars. If you’re just here to compete and drink beer, give turtle racing at Big Joe’s a (very slow) go. But born winners, beware—if your turtle comes in last place, you’ll earn a free drink. If you’ve seen enough action for the night, crawl back to your hotel near Navy Pier until it’s time to say “shell-o” the next morning.

Shop on the Wild Side: After you’ve perused the high-end shops on Michigan Avenue, why not drop the traditional same-old, and check out Chicago’s more eclectic side? You have to start at Wooly Mammoth, home to unusual curios and oddities like animal skulls, used prosthetic hooks, and taxidermy classes. Rotofugi is a local toy emporium that features unique vinyl toys, art, and enamel pins, and Lost Eras is a vintage shop with a hefty helping of showmanship, offering costumes, props, and antiques.

DIY Tasting Tour: Chicago is all about the eats, and that’s no secret sauce. Chicago-style hot dogs aren’t the only thing getting roasted at Wiener’s Circle—the iconic spot is beloved for employees yelling at and making fun of their customers. For Italian beef, Johnnie’s Beef is the (nearly) undisputed king of the perfect pepper-to-meat flavor blend. And, of course, there’s the deep dish pizza. The best pie in town is highly disputed, so try the staple spots: Giordano’s, Lou Malnati’s, and Pizzeria Uno will hardly even scratch the tomato-sauced surface of options. And after you’re impossibly full of the good stuff, roll on back to your downtown Chicago hotel to sleep it off.

Frequently Asked Questions About Chicago