
Illinois Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €1,284, price is now €880 per person
€880
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on 21 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 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 25 Aug 2025



The Langham, Chicago
Downtown Chicago
Price was €1,774, price is now €1,213 per person
€1,213
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 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 25 Aug 2025


The Langham, Chicago
Downtown Chicago
Price was €1,774, price is now €1,213 per person
€1,213
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,561, price is now €1,747 per person
€1,747
per person
10 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 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 25 Aug 2025


Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
The price is €462 per night from 7 Sept to 8 Sept
€462
7 Sept - 8 Sept
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,689 reviews)
"This property is beautiful and located in a great area."
Reviewed on 19 Aug 2025

The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
The price is €545 per night from 21 Sept to 22 Sept
€545
21 Sept - 22 Sept
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,001 reviews)
"Amazing stay as always"
Reviewed on 15 Aug 2025

The Peninsula Chicago
108 East Superior Street, Chicago, IL
The price is €626 per night from 1 Sept to 2 Sept
€626
1 Sept - 2 Sept
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,002 reviews)
"What a beautiful hotel but such a shame that every night, our hallway was filled the odor of pot. I asked 3 times about it and I guess it's allowed. I would consider a different hotel, if that's the case."
Reviewed on 23 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.