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.
Still Waters Resort

Still Waters Resort

4 out of 5
Save 100% on your flight
Price was $976, price is now $579 per person
$579
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) 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 Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
Save 100% on your flight
Price was $1,233, price is now $631 per person
$631
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) to Springfield (SGF)
Stay at this 3.5-star family-friendly resort in Branson. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Branson Landing and Silver Dollar City are located nearby.

The Inn at Vanessie

The Inn at Vanessie

4.5 out of 5
Downtown Santa Fe
Save 100% on your flight
Price was $1,573, price is now $964 per person
$964
per person
Nov 18 - Nov 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albuquerque (ABQ)
Stay at this 4.5-star luxury hotel in Santa Fe. Enjoy daily housekeeping, concierge services, and cable TV channels. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Santa Fe Plaza and Meow Wolf 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
Save 100% on your flight
Price was $1,131, price is now $707 per person
$707
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) to Springfield (SGF)
Stay at this 4-star business-friendly aparthotel in Branson. Enjoy free parking, a fitness center, and a 24-hour front desk. 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.

The Townhouses

The Townhouses

3 out of 5
Save 100% on your flight
Price was $1,192, price is now $769 per person
$769
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) to Springfield (SGF)
Stay at this 3-star aparthotel in Branson. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Branson Landing and Table Rock Lake are located nearby.

The Hacienda & Spa at Hotel Santa Fe

The Hacienda & Spa at Hotel Santa Fe

4.5 out of 5
Downtown Santa Fe
Save 100% on your flight
Price was $2,404, price is now $1,570 per person
$1,570
per person
Nov 18 - Nov 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albuquerque (ABQ)
Stay at this 4.5-star luxury hotel in Santa Fe. Enjoy free breakfast, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Santa Fe Plaza and Meow Wolf 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 ...
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. ...
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 ...
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 ...
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
1,466.68 km from city center
Stay at this 3.5-star business-friendly resort in Laughlin. Enjoy free WiFi, 7 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
1,069.34 km from city center
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 ...
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
1,068.54 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
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 free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
1,069.54 km from city center
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
1,070.35 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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. ...
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.

Frontier Airlines
Thu, Oct 2 - Sat, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Oct 2 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $145 found 2 days ago
Spirit Airlines
Sat, Oct 4 - Wed, Oct 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Oct 4 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 8, priced at $152 found 4 days ago
Alaska Airlines
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Oct 29 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $170 found 2 days ago
Delta
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 29 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $176 found 2 days ago
American Airlines
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Oct 29 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $197 found 2 days ago