Historic Route 66 Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Historic Route 66 Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $665, price is now $530 per person
$530
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Roman everything was clean everything was made that was all and it was very
Reviewed on Nov 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,033, price is now $731 per person
$731
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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.
1
Reviewed on Nov 4, 2026
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was $974, price is now $703 per person
$703
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
Price was $833, price is now $650 per person
$650
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Breakfast was good
Reviewed on Nov 4, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was $727, price is now $572 per person
$572
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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.
Eurostars Magnificent Mile
Downtown Chicago
Price was $822, price is now $676 per person
$676
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
This is my 3rd time staying at Eurostars and it was excellent as it always has been! Clean rooms, I appreciate the overnight valet, and it is in a great/safe location.
Reviewed on Nov 4, 2026
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See all available trips from Columbus to Historic Route 66
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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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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See all available properties in Historic Route 66
View all propertiesLowest 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.
Wed, Dec 2 - Sat, Dec 5
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Wed, Dec 2 - Sat, Dec 5
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Wed, Dec 2 - Sat, Dec 5
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$152 Roundtrip, found 6 days ago
$152
Roundtrip
found 6 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago