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Deals on vacations and trips to Historic Route 66
Save when you book Historic Route 66 package deals
Historic Route 66 flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/f5c69379_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Westin Michigan Avenue Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
![Still Waters Resort](https://images.trvl-media.com/lodging/1000000/430000/425400/425339/642d1798_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Still Waters Resort
Save 100% on your flight
per person
Aug 30 - Sep 3
found 6 hours ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
A marina, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free condo resort. Bring the family and enjoy the mini golf, children's pool, and free theme park shuttle. Enjoy the 2 spa tubs and perks like free self parking and free WiFi.
![Westgate Branson Woods Resort and Cabins](https://images.trvl-media.com/lodging/2000000/1190000/1188600/1188585/4892ab5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Westgate Branson Woods Resort and Cabins
Save 100% on your flight
per person
Aug 30 - Sep 3
found 6 hours ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
This smoke-free resort features 2 restaurants, 2 outdoor pools, and an indoor pool. Bring the family and enjoy the mini golf, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 9
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/387b811c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 9
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Top Historic Route 66 hotels deals
![Club Quarters Hotel, Central Loop, Chicago](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/2289d417_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $132 per night
$132
per night
Jul 1 - Jul 2
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
![Central Loop Hotel](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/b77965cb_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Central Loop Hotel
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $132 per night
$132
per night
Jul 1 - Jul 2
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.
![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/41255425_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $167 per night
$167
per night
Jul 3 - Jul 4
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
![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1676cf3d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $191 per night
$191
per night
Jul 1 - Jul 2
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/a97325e3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $171 per night
$171
per night
Jun 30 - Jul 1
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
![The Aquarius Casino Resort, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5073/d1c73999_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Aquarius Casino Resort, BW Premier Collection
1900 S Casino Dr, Laughlin, NV
Free Cancellation
Reserve now, pay when you stay
The price is $49 per night
$49
per night
Jun 16 - Jun 17
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.
Don't see what you're looking for?
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.
Popular places to visit
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
McCormick Place
4.5/5(1,805 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Photos of local treasures
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