Chicago Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
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Better together
Save up to ₹43,962 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
Stay at this 5-star luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,694 reviews)
Fantastic hotel
"The service, cleanliness, quality of rooms and every aspect is incredible!"
Reviewed on 17 Aug 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,003 reviews)
"Amazing stay as always"
Reviewed on 15 Aug 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,001 reviews)
"Peninsula is simply the best. Top notch service, amenities and everything in between."
Reviewed on 14 Aug 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.