Deals on vacations and trips to Historic Route 66

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Historic Route 66 flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.
Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (SGF)
This hotel features an outdoor pool and an indoor pool. There's fun for all ages with mini golf and a playground, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking.
The Inn at Vanessie

The Inn at Vanessie

4.5 out of 5
Downtown Santa Fe
Save 100% on your flight
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albuquerque (ABQ)
This hotel features express check-in, express check-out, and concierge services.
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (SGF)
This smoke-free resort features 2 outdoor pools, an indoor pool, and a restaurant. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Top Historic Route 66 hotels deals

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $154 total per night
$154 total
Aug 10 - Aug 11
Total includes taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.
Pet friendly
Free WiFi
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$170 nightly
The price is $200 total per night
$200 total
Aug 18 - Aug 19
Total includes taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
The Aquarius Casino Resort, BW Premier Collection

The Aquarius Casino Resort, BW Premier Collection

3.5 out of 5
1900 S Casino Dr, Laughlin, NV
Free Cancellation
Reserve now, pay when you stay
$58 nightly
The price is $66 total per night
$66 total
Jul 30 - Jul 31
Total includes taxes and fees
A casino, 4 restaurants, and an outdoor pool are all featured at this resort. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Relax with a drink at one of the 4 bars/lounges and enjoy the gym.
Pool
Free WiFi
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Free Cancellation
$281 nightly
The price is $324 total per night
$324 total
Aug 10 - Aug 11
Total includes taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $169 total per night
$169 total
Aug 17 - Aug 18
Total includes taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
$150 nightly
The price is $176 total per night
$176 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
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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.

Photos of local treasures

Browse Historic Route 66 vacation photos for more inspiration

Historic Route 66
Tulsa featuring a bridge, a city and a high rise building
Albuquerque which includes mountains
Albuquerque showing signage
Woody Guthrie Center showing outdoor art