Historic Route 66 Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Historic Route 66 Vacation Packages

Historic Route 66 Hotel Deals

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundable
The price is ₩203,025 per night from Oct 19 to Oct 20
₩203,025
₩238,331 total
Oct 19 - Oct 20
includes taxes & fees
8.6/10 Excellent! (3,355 reviews)
"Great location, amazing staff that were willing to help with the check in and clean rooms"

Reviewed on Sep 16, 2025

Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩205,471 per night from Oct 19 to Oct 20
₩205,471
₩241,203 total
Oct 19 - Oct 20
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
"Modern and Tech Savvy"

Reviewed on Sep 19, 2025

Central Loop Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩206,482 per night from Sep 22 to Sep 23
₩206,482
₩242,389 total
Sep 22 - Sep 23
includes taxes & fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"

Reviewed on Sep 18, 2025

Congress Plaza Hotel
See all 19,127 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.