Historic Route 66 Vacation Packages for 2026

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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 ...
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 ...
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 ...
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 ...
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr 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 ...
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 ...
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 ...
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 ...
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
1,069.54 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 ...
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 ...
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 ...
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 ...
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
1,068.94 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
1,069.31 km from city center
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 ...
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
1,069.93 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 ...
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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
Wed, Mar 18 - Tue, Mar 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Mar 18 from Los Angeles Intl. to O'Hare Intl., returning Tue, Mar 31, priced at $140 found 6 days ago
Spirit Airlines
Thu, May 7 - Tue, May 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 5 days ago
$188
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, May 7 from Los Angeles Intl. to O'Hare Intl., returning Tue, May 19, priced at $188 found 5 days ago
American Airlines
Wed, Feb 4 - Sun, Feb 8
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$310 Roundtrip, found 3 days ago
$310
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Feb 4 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Sun, Feb 8, priced at $310 found 3 days ago
Hawaiian Airlines
Tue, Mar 31 - Sat, Apr 18
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$314 Roundtrip, found 3 days ago
$314
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Tue, Mar 31 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Sat, Apr 18, priced at $314 found 3 days ago
Southwest Airlines
Wed, Feb 4 - Sun, Feb 8
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$320 Roundtrip, found 3 days ago
$320
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Feb 4 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Sun, Feb 8, priced at $320 found 3 days ago