Historic Route 66 All inclusive Holidays
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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,478, price is now €964 per person
€964
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on 26 Jan 2026
La Banque Hotel
Price was €1,379, price is now €1,002 per person
€1,002
per person
1 Apr - 7 Apr
found 15 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on 26 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 1 day 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
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View all tripsPrice 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 1 day 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 best hotel ! Always pleasant to stay !
Reviewed on 27 Jan 2026
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all tripsPrice found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,146, price is now €921 per person
€921
per person
3 Mar - 7 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on 26 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 1 day 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
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 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
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
