
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.

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $408, price is now $206 per person
$206
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,403, price is now $486 per person
$486
per person
Dec 23 - Dec 28
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 luxury 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.

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $585, price is now $310 per person
$310
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $396, price is now $211 per person
$211
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

The French Country Inn Lake Geneva
Save 100% on your flight
Price was $552, price is now $302 per person
$302
per person
Dec 31 - Jan 3
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A private beach and a restaurant are featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, luggage storage, and concierge services are also on offer.
Top Historic Route 66 hotels deals

Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $104 total per night
$104 total
Nov 23 - Nov 24
Total with 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

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $145 total per night
$145 total
Dec 21 - Dec 22
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $102 total per night
$102 total
Dec 21 - Dec 22
Total with taxes and fees
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.
Pool
Breakfast included

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $98 total per night
$98 total
Dec 7 - Dec 8
Total with 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

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $136 total per night
$136 total
Nov 24 - Nov 25
Total with 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

citizenM Chicago Downtown
80 East Wacker Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $126 total per night
$126 total
Dec 8 - Dec 9
Total with 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. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
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.
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