Historic Route 66 Vacation Packages for 2025

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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
Book a stay at this 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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
1,068.83 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
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
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast 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
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
1,069.74 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 ...
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 ...
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
1,069.26 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
1,069.85 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
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 ...
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 ...
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
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
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 ...
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
900 E Grand Chicago IL
1,071.1 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 restaurant and the helpful ...
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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, Dec 4 - Thu, Dec 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 5 days ago
$73
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Los Angeles Intl. to O'Hare Intl., returning Thu, Dec 11, priced at $73 found 5 days ago
Spirit Airlines
Wed, Dec 3 - Tue, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Dec 3 from Los Angeles Intl. to O'Hare Intl., returning Tue, Dec 9, priced at $118 found 5 days ago
Delta
Tue, Feb 10 - Sat, Feb 14
LAX
Los Angeles Intl.
ABQ
Albuquerque Intl. Sunport
$231 Roundtrip, found 18 hours ago
$231
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Feb 10 from Los Angeles Intl. to Albuquerque Intl. Sunport, returning Sat, Feb 14, priced at $231 found 18 hours ago
American Airlines
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Dec 5 from Los Angeles Intl. to O'Hare Intl., returning Sun, Dec 7, priced at $234 found 2 days ago
United
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
Select United flight, departing Fri, Dec 5 from Los Angeles Intl. to O'Hare Intl., returning Sun, Dec 7, priced at $234 found 2 days ago