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.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 18
found 14 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
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 and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this eco-certified 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.

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 18
found 14 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
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. Popular attractions Michigan Avenue and Chicago Riverwalk 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 ...
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 ...
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 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. ...
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 ...
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 ...
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
1,068.41 km from city center
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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 a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
1,069.71 km from city center
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
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 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 ...
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 ...
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
1,067.36 km from city center
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
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. ...
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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
Wed, Jul 2 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jul 2 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $130 found 1 day ago
Spirit Airlines
Wed, Jun 4 - Sun, Jun 8
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$149 Roundtrip, found 6 days ago
$149
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Jun 4 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Sun, Jun 8, priced at $149 found 6 days ago
Frontier Airlines
Mon, May 19 - Sat, May 24
LAX
Los Angeles Intl.
MDW
Midway Intl.
$162 Roundtrip, found 8 hours ago
$162
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, May 19 from Los Angeles Intl. to Midway Intl., returning Sat, May 24, priced at $162 found 8 hours ago
Frontier Airlines
Wed, Jun 4 - Wed, Jun 11
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$260 Roundtrip, found 3 days ago
$260
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jun 4 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Wed, Jun 11, priced at $260 found 3 days ago