South Side Ski Holidays
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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,077, price is now €867 per person
€867
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff all very nice and helpful. Clean, beautifully decorated for the holidays. Wonderful experience. Highly recommend.
Reviewed on 16 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,721, price is now €1,228 per person
€1,228
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on 14 Dec 2025
The Peninsula Chicago
Downtown Chicago
Price was €1,986, price is now €1,510 per person
€1,510
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived.
Outstanding!!
Reviewed on 15 Dec 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,131, price is now €880 per person
€880
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on 8 Dec 2025
Pendry Chicago
Downtown Chicago
Price was €1,161, price is now €929 per person
€929
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on 4 Dec 2025
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,721, price is now €1,228 per person
€1,228
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on 14 Dec 2025
The Peninsula Chicago
Downtown Chicago
Price was €1,986, price is now €1,510 per person
€1,510
per person
25 Jan - 30 Jan
found 12 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived.
Outstanding!!
Reviewed on 15 Dec 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
