Chicago Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
Better together
Save up to ₹43,962 when you book a flight and hotel together*
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Top flight + Luxury hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,822 reviews)
Advertised a pool and breakfast was included. The pool was closed and there was no breakfast. I was offered a credit for breakfast at the restaurant, used it, and then was billed for it.
Reviewed on 1 Jul 2025
5* Luxury holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
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 ...
9.2/10 Wonderful! (1,627 reviews)
"Walkable and safe"
Reviewed on 29 Jun 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)
"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 30 Jun 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! (1,005 reviews)
"Always love our stay at The Peninsula!"
Reviewed on 29 Jun 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.
More Holiday Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.