Historic Route 66 Ski Holidays
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Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €1,073, price is now €940 per person
€940
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18/10 Exceptional! (2,204 reviews)
The room was clean, staff was very friendly. Coffee available. Overall very happy with our stay
Reviewed on 9 Nov 2025
Pendry Chicago
Downtown Chicago
Price was €1,274, price is now €1,045 per person
€1,045
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,128 reviews)
Staff was our favorite part! Very very professional and friendly
Reviewed on 14 Nov 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,225, price is now €1,055 per person
€1,055
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (3,388 reviews)
Clean room, GREAT location, nice rooftop space.
Nice bath products.
Reviewed on 13 Nov 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €1,137, price is now €1,010 per person
€1,010
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great stay as always- beautiful property, rooms, Game Room is a gem, and excellent staff; just a couple notes:
Bring back The Milk Room!
The lobby seating was less inviting with so much turned over to assigned-seating dining.
Can the hotel offer at least complimentary coffee/tea for guests? I prepaid for breakfast but still had to pay $5 per cup of coffee.
Reviewed on 9 Nov 2025
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View all tripsPrice found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was €1,274, price is now €1,045 per person
€1,045
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,128 reviews)
Staff was our favorite part! Very very professional and friendly
Reviewed on 14 Nov 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,225, price is now €1,055 per person
€1,055
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (3,388 reviews)
Clean room, GREAT location, nice rooftop space.
Nice bath products.
Reviewed on 13 Nov 2025
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
