Historic Route 66 Vacation Packages for 2026

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Historic Route 66 Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,455, price is now $979 per person
$979
per person
Jul 26 - Jul 30
found 17 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Save 100% on your flight
Price was $2,246, price is now $1,168 per person
$1,168
per person
Jul 23 - Jul 30
found 17 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Springfield (SGF)
Book a stay at this 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.

Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
Shepherd of the Hills
Save 100% on your flight
Price was $2,203, price is now $1,308 per person
$1,308
per person
Jul 23 - Jul 30
found 17 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Springfield (SGF)
Book a stay at this 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 Table Rock Lake are located nearby.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,528, price is now $1,020 per person
$1,020
per person
Jul 26 - Jul 30
found 17 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,614, price is now $1,121 per person
$1,121
per person
Jul 26 - Jul 30
found 16 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,744, price is now $1,244 per person
$1,244
per person
Jul 26 - Jul 30
found 17 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

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Top Hotel Deals

Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
1,068.47 km from city center
Book a stay at this 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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
1,069.75 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
Avi Resort & Casino

Avi Resort & Casino

3.5 out of 5
10000 Aha Macav Pkwy Laughlin NV
1,476.33 km from city center
Book a stay at this beach hotel in Laughlin. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
1,069.91 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
1,069.19 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
1,069.28 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
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
Book a stay at this business-friendly resort in Laughlin. Enjoy free WiFi, an outdoor pool, and 7 restaurants. Our guests praise the helpful staff and the clean ...
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
1,069.39 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
1,069.88 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool 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 ...
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
1,068.37 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
1,069.98 km from city center
Book a stay at this 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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
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 luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
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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
Tue, Jul 21 - Wed, Jul 29
LAX
Los Angeles Intl.
OKC
Will Rogers World
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Los Angeles Intl. to Will Rogers World, returning Wed, Jul 29, priced at $200 found 2 days ago
Delta
Tue, Jul 7 - Wed, Jul 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$219 Roundtrip, just found
$219
Roundtrip
just found
Select Delta flight, departing Tue, Jul 7 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $219 just found
United
Wed, Aug 19 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 5 hours ago
$219
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Aug 19 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $219 found 5 hours ago
Southwest Airlines
Tue, Aug 25 - Tue, Sep 8
LAX
Los Angeles Intl.
MDW
Midway Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Aug 25 from Los Angeles Intl. to Midway Intl., returning Tue, Sep 8, priced at $229 found 1 day ago
American Airlines
Sat, Jul 4 - Tue, Jul 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 5 hours ago
$238
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Jul 4 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 7, priced at $238 found 5 hours ago