Chicago Luxury Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to €185 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
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was €2,042, price is now €1,784 per person
€1,784
per person
14 May - 17 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar 2026
Hilton Chicago
Downtown Chicago
Price was €2,063, price is now €1,873 per person
€1,873
per person
14 May - 17 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,658 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on 12 Mar 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was €1,942, price is now €1,789 per person
€1,789
per person
14 May - 17 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,016 reviews)
Nice clean room with tons of historic charm. Love the duvets and view to Millennium Park
Reviewed on 9 Mar 2026
Price found within the past 48 hours. Click for updated prices.
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was €2,042, price is now €1,784 per person
€1,784
per person
14 May - 17 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar 2026
Hilton Chicago
Downtown Chicago
Price was €2,063, price is now €1,873 per person
€1,873
per person
14 May - 17 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,658 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on 12 Mar 2026
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! (1,847 reviews)
Room was perfect/staff was great
Reviewed on 12 Mar 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 ...
9.8/10 Exceptional! (1,000 reviews)
Room view was awful. Room was average
Reviewed on 11 Mar 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 ...
9.8/10 Exceptional! (1,001 reviews)
Outstanding service and food. Ideally located for shopping and restaurants.
Reviewed on 12 Mar 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
