Historic Route 66 Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Historic Route 66

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.187.690 ₫ per night from 23 Dec to 24 Dec
2.187.690 ₫
2.568.089 ₫ total
23 Dec - 24 Dec
includes taxes & fees
8.6/10 Excellent! (3,307 reviews)
Good location, quiet room, comfy bed

Reviewed on 13 Dec 2025

Club Quarters Hotel, Central Loop, Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.135.602 ₫ per night from 5 Jan to 6 Jan
2.135.602 ₫
2.506.984 ₫ total
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,478 reviews)
The rooms are clean and well-maintained, and they’re conveniently located near a variety of shops.

Reviewed on 13 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,113 reviews)
The staff is so friendly and helpful. We now have stayed here twice and enjoy the hotel.

Reviewed on 11 Dec 2025

Get rates
Silversmith Hotel Chicago Downtown
See all 19,705 properties in Historic Route 66
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.