Historic Route 66 Holidays

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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 €82 per night from 19 Jan to 20 Jan
€82
19 Jan - 20 Jan
includes taxes & fees
8.6/10 Excellent! (3,352 reviews)
Nice staff, room clean

Reviewed on 3 Jan 2026

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 €90 per night from 12 Jan to 13 Jan
€90
12 Jan - 13 Jan
includes taxes & fees
8.8/10 Excellent! (3,645 reviews)
Great hotel

Reviewed on 2 Jan 2026

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €164 per night from 13 Jan to 14 Jan
€164
13 Jan - 14 Jan
includes taxes & fees
8.4/10 Very Good! (2,484 reviews)
The room was very clean, I do wish there was a little better lighting in the closet (which was walking!!). The hotel has so much history and is just fun to walk around and explore the first and second levels. The check-in staff are professional and quick. They text you and are very responsive. The ...

Reviewed on 5 Jan 2026

Hilton Chicago
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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