Chicago Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was €791, price is now €668 per person
€668
per person
31 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,018 reviews)
Beautiful building, great customer service and amenities, and awesome location!
Reviewed on 4 Sep 2025
21c Museum Hotel Chicago
Downtown Chicago
Price was €844, price is now €719 per person
€719
per person
31 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,660 reviews)
Parking is nearby. Our suite was in front of the street and it was really loud every night. Something to consider as some people are sensible to noise. There was no fridge as well. Overall it was great as it was clean, new and well maintained.
Reviewed on 5 Sep 2025
L7 Chicago by LOTTE
Downtown Chicago
Price was €1,261, price is now €1,082 per person
€1,082
per person
30 Oct - 2 Nov
found 8 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.6/10 Exceptional! (2,896 reviews)
Right in the middle of everything. Great for first time visitors.
Reviewed on 5 Sep 2025
The Godfrey Hotel Chicago
Downtown Chicago
Price was €1,270, price is now €1,091 per person
€1,091
per person
30 Oct - 2 Nov
found 8 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
8.6/10 Excellent! (1,917 reviews)
Enjoy the rooftop on level 4. Friendly staff. Room was clean and Bed was comfortable. Would stay again 😊
Reviewed on 6 Sep 2025
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was €1,555, price is now €1,336 per person
€1,336
per person
31 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Truly enjoyed our experience at this hotel. Staff very kind and helpful. Location was perfect because of its location on the Magnificent Mile and getting to other areas of interest in Chicago. The room was very comfortable and clean. Definitely recommend this hotel!
Reviewed on 4 Sep 2025
The Langham, Chicago
Downtown Chicago
Price was €3,812, price is now €3,463 per person
€3,463
per person
13 Nov - 19 Nov
found 1 day ago
Return direct flight included
Thessaloniki (SKG) to Chicago (ORD)
9.8/10 Exceptional! (1,005 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.
L7 Chicago by LOTTE
Downtown Chicago
Price was €1,261, price is now €1,082 per person
€1,082
per person
30 Oct - 2 Nov
found 8 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.6/10 Exceptional! (2,896 reviews)
Right in the middle of everything. Great for first time visitors.
Reviewed on 5 Sep 2025
The Godfrey Hotel Chicago
Downtown Chicago
Price was €1,270, price is now €1,091 per person
€1,091
per person
30 Oct - 2 Nov
found 8 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
8.6/10 Excellent! (1,917 reviews)
Enjoy the rooftop on level 4. Friendly staff. Room was clean and Bed was comfortable. Would stay again 😊
Reviewed on 6 Sep 2025
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €955, price is now €706 per person
€706
per person
31 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.
Reviewed on 4 Sep 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,837, price is now €1,194 per person
€1,194
per person
31 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service
Reviewed on 4 Sep 2025
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
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 ...
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
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 ...
The Peninsula Chicago
108 East Superior Street, Chicago, IL
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 ...
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.
