Chicago Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,665, price is now €1,225 per person
€1,225
per person
14 Mar - 18 Mar
found 11 hours ago
Return flight included
Dublin (DUB) 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
Save 100% on your flight
Price was €2,462, price is now €1,834 per person
€1,834
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) 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
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,209, price is now €914 per person
€914
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,196, price is now €935 per person
€935
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop!
Reviewed on 26 Jan 2026
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,665, price is now €1,225 per person
€1,225
per person
14 Mar - 18 Mar
found 11 hours ago
Return flight included
Dublin (DUB) 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
Save 100% on your flight
Price was €2,462, price is now €1,834 per person
€1,834
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) 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
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,358, price is now €1,110 per person
€1,110
per person
3 Mar - 7 Mar
found 12 hours ago
Return flight included
Dublin (DUB) 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
Price was €1,665, price is now €1,225 per person
€1,225
per person
14 Mar - 18 Mar
found 11 hours ago
Return flight included
Dublin (DUB) 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 €1,885, price is now €1,559 per person
€1,559
per person
3 Mar - 7 Mar
found 12 hours ago
Return flight included
Dublin (DUB) 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
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! (1,003 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! (1,007 reviews)
Excellent Hotel. Excellent staff and service. Excellent location.
Reviewed on 19 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
