Historic Route 66 Vacation Packages for 2025

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Historic Route 66 Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
per person
Jul 8 - Jul 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Springfield (SGF)
Stay at this 3.5-star family-friendly resort in Branson. Enjoy free parking, 2 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Branson Landing and Silver Dollar City are located nearby.

Still Waters Resort

Still Waters Resort

4 out of 5
Save 100% on your flight
per person
Jul 8 - Jul 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Springfield (SGF)
Stay at this 4-star family-friendly condo in Branson. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Silver Dollar City and Table Rock Lake are located nearby.

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
per person
Jul 8 - Jul 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Springfield (SGF)
Stay at this 4-star family-friendly hotel in Hollister. Enjoy free parking, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Table Rock Lake and Top of the Rock Golf Course are located nearby.

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

4 out of 5
per person
Jul 8 - Jul 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Springfield (SGF)
Stay at this 4-star family-friendly aparthotel in Branson. Enjoy free parking, an outdoor pool, and 2 hot tubs. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Table Rock Lake and Silver Dollar City are located nearby.

Stormy Point Village Resort

Stormy Point Village Resort

4 out of 5
per person
Jul 8 - Jul 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Springfield (SGF)
Stay at this 4-star family-friendly aparthotel in Branson. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Silver Dollar City and Table Rock Lake are located nearby.

Palace View Heights by Spinnaker Resorts

Palace View Heights by Spinnaker Resorts

3.5 out of 5
per person
Jul 8 - Jul 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Springfield (SGF)
Stay at this 3.5-star business-friendly condo in Branson. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Branson Landing and Table Rock Lake are located nearby.

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Top Hotel Deals

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
1,068.46 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street, Chicago, IL
1,068.47 km from city center
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
1,068.76 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy, Chicago, IL
1,070 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
1,069.75 km from city center
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
1,069.29 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
1,069.28 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive, Chicago, IL
1,069.54 km from city center
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
1,070.15 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
1,069.58 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St, Chicago, IL
1,069.93 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
1,069.35 km from city center
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
1,069.4 km from city center
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
1,069.98 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
1,069.2 km from city center
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
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See all available properties in Historic Route 66
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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.

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.

Spirit Airlines
Sat, Jul 5 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Jul 5 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $110 found 4 days ago
Frontier Airlines
Wed, Jun 25 - Sat, Jul 5
LAX
Los Angeles Intl.
OKC
Will Rogers World
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jun 25 from Los Angeles Intl. to Will Rogers World, returning Sat, Jul 5, priced at $210 found 2 days ago
Spirit Airlines
Thu, Jun 12 - Sun, Jun 15
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$213 Roundtrip, found 2 days ago
$213
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Jun 12 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Sun, Jun 15, priced at $213 found 2 days ago
American Airlines
Sat, Jun 28 - Wed, Jul 2
LAX
Los Angeles Intl.
TUL
Tulsa Intl.
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 28 from Los Angeles Intl. to Tulsa Intl., returning Wed, Jul 2, priced at $304 found 1 day ago