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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €1,670, price is now €1,016 per person
€1,016
per person
29 Jul - 3 Aug
found 14 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation.
Other than that we had a very enjoyable stay. The location is great!
Reviewed on 19 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was €2,197, price is now €1,315 per person
€1,315
per person
29 Jul - 3 Aug
found 14 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again.
Reviewed on 21 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was €2,214, price is now €1,359 per person
€1,359
per person
29 Jul - 3 Aug
found 14 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again.
Reviewed on 21 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,250, price is now €1,436 per person
€1,436
per person
29 Jul - 3 Aug
found 14 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin
Reviewed on 18 May 2026
Top hotels in Historic Route 66
Central Loop Hotel
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €112 per night from 26 May to 27 May
€112
26 May - 27 May
includes taxes & fees
8.6/10 Excellent! (2,146 reviews)
"More direction evident for self check in but good stay"
Reviewed on 21 May 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €137 per night from 25 May to 26 May
€137
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,128 reviews)
"Bring earplugs, people love driving down Michigan avenue blasting music loudly"
Reviewed on 22 May 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €187 per night from 27 May to 28 May
€187
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,210 reviews)
"The hotel was marvelous. The breakfasts were amazing. Anything you could think of was there. The rooftop bar is definitely worth visiting."
Reviewed on 22 May 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
