Chicago Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Price was €1,655, price is now €1,285 per person
€1,285
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,403 reviews)
Beaux art beauty in downtown Chicago, walkable from Union Station and close to everything. History, charm, great for a weekend stay.
Reviewed on 27 Apr 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,853, price is now €1,310 per person
€1,310
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on 24 Apr 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was €1,727, price is now €1,285 per person
€1,285
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.
Reviewed on 22 Apr 2026
Price found within the past 48 hours. Click for updated prices.
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! (1,856 reviews)
Absolutely fantastic will be back
Reviewed on 27 Apr 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! (1,005 reviews)
Our stay at The Langham was nothing short of exceptional. Perfectly located, the hotel offers an exquisite setting within close proximity to everything, allowing for a seamless and enriching experience of the city. Our room was impeccable—spacious, elegantly appointed, and equipped with every comfort ...
Reviewed on 28 Apr 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)
Best Hotel in Chicago
Reviewed on 27 Apr 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.
