Chicago Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
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Save up to ₩234,741 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Luxury Chicago Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
Trump International Hotel & Tower Chicago is a lush 5-star boutique property where you can be treated to deep soaking bathtubs and pillowtop beds. The spa, indoor ...
9.2/10 Wonderful! (1,626 reviews)
"Beautiful"
Reviewed on Jul 3, 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
Enjoy a posh stay at The Langham, Chicago, where you'll find deep soaking bathtubs and a champagne service. Deluxe amenities at this hotel include a spa, an ...
9.6/10 Exceptional! (1,004 reviews)
"The Langham is quite possibly the best hotel I've ever stayed at. The staff were absolutely amazing and the hotel itself was so clean. The hallways smelled so good too which I know is a weird observation but the wood they used for the floors and doors were so aromatic and it was something my party ..."
Reviewed on Jun 30, 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
Treat yourself to some luxurious accommodations at The Peninsula Chicago, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe ...
9.8/10 Exceptional! (1,006 reviews)
"Always love our stay at The Peninsula!"
Reviewed on Jun 29, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.