Chicago Luxury Vacations
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Save up to NT$5,067 when you book a flight and hotel together*
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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! (1,693 reviews)
"It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence."
Reviewed on 2025/8/25
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! (1,003 reviews)
Luxury retreat!
"The Langham is ALWAYS a luxury treat! This was my birthday staycation and they did not disappoint. They upgraded me to a luxe suite, champagne, and a mini cake! The spa is the best in the city! Always choose The Langham when in Chicago!"
Reviewed on 2025/8/24
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! (1,005 reviews)
"Fantastic hotel"
Reviewed on 2025/8/25
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.