
Chicago Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₹43,962 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top flight + Luxury hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ₹54,038, price is now ₹43,064 per person
₹43,064
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (2,208 reviews)
Beautiful facility, great location, nice bed, good shower.
Reviewed on 25 Jan 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₹109,038, price is now ₹82,069 per person
₹82,069
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ₹59,597, price is now ₹46,909 per person
₹46,909
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ₹72,551, price is now ₹57,711 per person
₹57,711
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,266 reviews)
Everything was great. Love the restaurant and bar, staff was friendly and helpful
Reviewed on 14 Jan 2026

The Peninsula Chicago
Downtown Chicago
Price was ₹122,801, price is now ₹99,577 per person
₹99,577
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
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
Price was ₹109,038, price is now ₹82,069 per person
₹82,069
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026

The Peninsula Chicago
Downtown Chicago
Price was ₹122,801, price is now ₹99,577 per person
₹99,577
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
3 Night Luxury holidays in Chicago
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ₹59,597, price is now ₹46,909 per person
₹46,909
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₹109,038, price is now ₹82,069 per person
₹82,069
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ₹72,551, price is now ₹57,711 per person
₹57,711
per person
9 Apr - 12 Apr
found 9 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,266 reviews)
Everything was great. Love the restaurant and bar, staff was friendly and helpful
Reviewed on 14 Jan 2026
Top Luxury Chicago Hotels

Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,820 reviews)
Great
Reviewed on 20 Jan 2026

The Langham, Chicago
330 North Wabash Avenue Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,004 reviews)
Yes
Reviewed on 21 Jan 2026

The Peninsula Chicago
108 East Superior Street Chicago IL
Stay at this 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 ...
9.6/10 Exceptional! (1,011 reviews)
Amazing staff. Sooooo clean. Top service
Reviewed on 25 Jan 2026
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.
