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.
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
O'Hare
Save 100% on your flight
per person
Jun 11 - Jun 15
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena 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 14 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.

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 11 - Jun 15
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 11 - Jun 15
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 5 - Jun 9
found 6 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.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 11 - Jun 15
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

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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 ...
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. ...
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 ...
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, 4 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
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 ...
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 ...
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 ...
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 ...
Avi Resort & Casino

Avi Resort & Casino

3.5 out of 5
10000 Aha Macav Pkwy, Laughlin, NV
1,476.33 km from city center
Stay at this 3.5-star 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. ...
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
1,069.2 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff 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 ...
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 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. ...
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
Wed, Jun 4 - Sun, Jun 8
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$149 Roundtrip, found 19 hours ago
$149
Roundtrip
found 19 hours 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 19 hours ago
Frontier Airlines
Wed, May 14 - Tue, May 20
LAX
Los Angeles Intl.
OKC
Will Rogers World
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 14 from Los Angeles Intl. to Will Rogers World, returning Tue, May 20, priced at $188 found 3 days ago
American Airlines
Wed, Jul 16 - Sun, Jul 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 16 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jul 20, priced at $201 found 1 day ago
Frontier Airlines
Sat, May 3 - Wed, May 7
LAX
Los Angeles Intl.
MDW
Midway Intl.
$290 Roundtrip, found 6 days ago
$290
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 3 from Los Angeles Intl. to Midway Intl., returning Wed, May 7, priced at $290 found 6 days ago