Historic Route 66 Vacation Packages for 2026

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Historic Route 66 Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

Downtown Chicago
$632
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$818
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$1,203
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on Oct 2, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$711
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
Save 100% on your flight
$1,013
per person
Nov 5 - Nov 10
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

Downtown Chicago
Save 100% on your flight
$1,016
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Fantastic as always. Highly recommend

Reviewed on Oct 1, 2026

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Top Hotel Deals

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area

950 N Grand Canyon Blvd Williams AZ
1,227.14 km from city center
Book a stay at this golf hotel in Williams. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Quality Inn Holbrook near Petrified Forest

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ
1,054.15 km from city center
Book a stay at this business-friendly hotel in Holbrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The L Motel - Downtown Flagstaff

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ
1,181.13 km from city center
Stay at this motel in Flagstaff. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Americas Best Value Inn & Suites Flagstaff

Americas Best Value Inn & Suites Flagstaff

1990 E. Route 66 Flagstaff AZ
1,177.98 km from city center
Book a stay at this business-friendly motel in Flagstaff. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

14125 Hwy Z, I-44 and Hwy 28 Exit 163 St. Robert MO
589.9 km from city center
Book a stay at this business-friendly motel in St. Robert. Enjoy free parking, a 24-hour front desk, and a business center. Our guests praise the helpful staff ...
Dwell Lake Havasu

Dwell Lake Havasu

14215 Oatman Hwy Topock AZ
1,443.15 km from city center
Stay at this cabin in Topock. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Moabi Regional Park and Havasu National Wildlife Refuge ...
Claremore Motor Inn

Claremore Motor Inn

1709 N Lynn Riggs Blvd Claremore OK
282.34 km from city center
Stay at this motel in Claremore. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loshbaugh Kiddie Park and Pecan Park are located ...
Magnuson Grand Hotel And Conference Center

Magnuson Grand Hotel And Conference Center

19067 W Frontage Rd Raymond IL
831.91 km from city center
Book a stay at this business-friendly hotel in Raymond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Lake Lou Yeager and Raymond Shoal ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Delta
Sat, Oct 31 - Tue, Nov 3
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$177
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 31 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Tue, Nov 3, priced at $177 found 1 day ago
American Airlines
Southwest Airlines
United