Wheels Up 🍕 Deep Dish Down – 3 Nights in Chicago Is Calling You

Ready for a getaway that’s bigger than just a bestie trip? Round up your favorite people and grab this amazing deal — 3 nights in Chicago with flights included starting at just $297!

Whether your crew is all about deep-dish pizza, jazz clubs, museum hopping, or just soaking up the city vibes, Chicago has something for everyone. Think skyline views, lakeside strolls, and enough eats and entertainment to keep the whole gang smiling.

Stay in style at the Ambassador Chicago (4.3/5 on Trip Advisor). You’ll be just steps from Oak Street Beach, designer shopping on the Magnificent Mile, and some of the city’s best restaurants and nightlife. Enjoy chic rooms that mix historic charm with modern touches — plus perks like a 24-hour fitness center and rooftop views.

Fun fact: this spot has hosted legends like Frank Sinatra, Marilyn Monroe, and Elizabeth Taylor — and now it’s your turn to live like a star.

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All of our deals are available at the time of publishing, but prices are subject to fluctuate and change at any time.

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