
Historic Route 66 Holidays
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Top Flight + Hotel Deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was €1,276, price is now €844 per person
€844
per person
4 Oct - 10 Oct
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,621 reviews)
Check in was easy and it felt very safe. Room was clean and was good sized for a Chicago hotel.
Reviewed on 21 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025


Park Hyatt Chicago
Downtown Chicago
Price was €1,968, price is now €1,235 per person
€1,235
per person
2 Nov - 7 Nov
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €1,712, price is now €1,116 per person
€1,116
per person
4 Oct - 10 Oct
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on 21 Aug 2025
Top hotels in Historic Route 66

Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundable
The price is €117 per night from 2 Sept to 3 Sept
€117
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (3,343 reviews)
"Awesome spot"
Reviewed on 19 Aug 2025

Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €117 per night from 2 Sept to 3 Sept
€117
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,810 reviews)
"N/a"
Reviewed on 19 Aug 2025

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €153 per night from 1 Sept to 2 Sept
€153
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"
Reviewed on 19 Aug 2025
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.
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