Historic Route 66 Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Historic Route 66 Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
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. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Kansas City (MCI) 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.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Kansas City (MCI) 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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See all available trips from Columbus to Historic Route 66
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Embassy Suites by Hilton Chicago Downtown River North
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. ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
1,069.58 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Hilton Chicago/Magnificent Mile Suites
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
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 ...
Congress Plaza Hotel
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 ...
The Wade
644 N Lake Shore Dr, Chicago, IL
1,070.35 km from city center
Stay at this 4.5-star luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
Avi Resort & Casino
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. ...
Freehand Chicago
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. ...
Swissotel - Chicago
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 ...
Hotel Felix River North/Magnificent Mile
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 ...
The Aquarius Casino Resort, BW Premier Collection
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
1,070 km from city center
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place, Chicago, IL
1,070.21 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Don't see what you're looking for?
See all available properties in Historic Route 66
View all propertiesLowest 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.
Tue, Jul 29 - Wed, Aug 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Sat, Aug 2 - Tue, Aug 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Wed, Jul 9 - Sun, Jul 13
LAX
Los Angeles Intl.
OKC
Will Rogers World
$268 Roundtrip, found 20 hours ago
$268
Roundtrip
found 20 hours ago
Thu, Jun 26 - Mon, Jul 7
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$282 Roundtrip, found 2 days ago
$282
Roundtrip
found 2 days ago
Best points of interest in Historic Route 66
- Route 66 Raceway Vacations
- Route 66 Casino Vacations
- Springfield Expo Center Vacations
- Symphony Center Vacations
- National Route 66 Museum Vacations
- The Blue Whale Vacations
- Route 66 Vintage Iron Motorcycle Museum Vacations
- Chicago Board of Trade Building Vacations
- Route 66 Carousel Park Vacations
- El Rey Theater Vacations
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