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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $773, price is now $495 per person
$495
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,353, price is now $824 per person
$824
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

4 out of 5
Skyview
Save 100% on your flight
Price was $1,306, price is now $808 per person
$808
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (SGF)
A gym, free self parking, and concierge services are featured at this hotel. Business travelers can take advantage of the express check-out. A garden, a picnic area, and barbecue grills are also on offer.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,366, price is now $856 per person
$856
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,211, price is now $786 per person
$786
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Top Historic Route 66 hotels deals

Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $138 total per night
$138 total
May 25 - May 26
Total with taxes and fees
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.
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
$62 nightly
The price is $70 total per night
$70 total
Apr 29 - Apr 30
Total with taxes and fees
A casino, 7 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. Make the most of the gym and seasonal outdoor pool, and relax with drinks at one of the 4 bars/lounges.
Pool
Free WiFi
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $148 total per night
$148 total
May 25 - May 26
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Pet friendly
Free WiFi
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$117 nightly
The price is $137 total per night
$137 total
Apr 30 - May 1
Total with taxes and fees
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
Avi Resort & Casino

Avi Resort & Casino

3.5 out of 5
10000 Aha Macav Pkwy Laughlin NV
$52 nightly
The price is $59 total per night
$59 total
May 6 - May 7
Total with taxes and fees
A private beach, a casino, and 2 outdoor pools are all featured at this hotel. There's fun for all ages with a playground and an arcade/game room, and babysitting is an added bonus. Enjoy the 2 hot tubs and perks like free valet parking and free WiFi.
On private beach
Pool
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
$139 nightly
The price is $165 total per night
$165 total
May 10 - May 11
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.
Pool
Pet friendly
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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.

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