Historic Route 66 Mountain Holidays
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Top flight + Mountain hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
This hotel is designed well and has a great little bar downstairs along with a nice restaurant/cafe adjacent to the property. The front desk girls are mostly helpful specifically Muriel who made my stay extremely comfortable and gave me tons of recs on eats, etc. I was so thankful to have her around!
I had AC issues with a crazy rattling noise in my first room and was upgraded to another nicer room my last night there. Neither of the beds were very comfortable - I think adding a pillow top would be helpful! The rooms are cute though!
Reviewed on 14 Jul 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on 16 Jul 2025
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all trips5* Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on 16 Jul 2025
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all trips3 Night Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
This hotel is designed well and has a great little bar downstairs along with a nice restaurant/cafe adjacent to the property. The front desk girls are mostly helpful specifically Muriel who made my stay extremely comfortable and gave me tons of recs on eats, etc. I was so thankful to have her around!
I had AC issues with a crazy rattling noise in my first room and was upgraded to another nicer room my last night there. Neither of the beds were very comfortable - I think adding a pillow top would be helpful! The rooms are cute though!
Reviewed on 14 Jul 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!
Reviewed on 16 Jul 2025
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all trips4 Night Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Central Loop
Downtown Chicago
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,138 reviews)
The only thing I was disappointed about was the fact that their “hot new restaurant” Seville, is only open on weekdays. No weekend hours!
Reviewed on 16 Jul 2025
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See all available trips from London to Historic Route 66
View all tripsMore holidays you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.