Historic Route 66 Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Historic Route 66 Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,155, price is now $675 per person
$675
per person
May 7 - May 12
found 14 hours ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,796, price is now $1,032 per person
$1,032
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,551, price is now $1,048 per person
$1,048
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
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 in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,857, price is now $1,284 per person
$1,284
per person
May 4 - May 11
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 $2,072, price is now $1,436 per person
$1,436
per person
May 4 - May 11
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.

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 $1,196, price is now $843 per person
$843
per person
May 4 - May 11
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 ...
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 ...
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 ...
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 ...
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, 7 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
The Wade

The Wade

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

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
1,069.89 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. ...
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
1,069.49 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Don Laughlin's Riverside Resort Hotel & Casino

Don Laughlin's Riverside Resort Hotel & Casino

3 out of 5
1650 S Casino Drive Laughlin NV
1,466.39 km from city center
Book a stay at this spa resort in Laughlin. Enjoy free parking, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our ...
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
1,069.72 km from city center
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 ...
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 ...
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 ...
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
1,069.41 km from city center
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
1,068.58 km from city center
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
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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
Fri, Apr 17 - Tue, Apr 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 28, priced at $109 found 1 day ago
Spirit Airlines
Wed, Apr 15 - Sat, May 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Apr 15 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 2, priced at $195 found 1 day ago
Delta
Wed, May 6 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 6 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 13, priced at $237 found 1 day ago
Southwest Airlines
Tue, Sep 8 - Tue, Sep 15
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$287 Roundtrip, found 2 days ago
$287
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Sep 8 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Tue, Sep 15, priced at $287 found 2 days ago
American Airlines
Wed, Apr 22 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$288 Roundtrip, found 19 hours ago
$288
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 13, priced at $288 found 19 hours ago