Historic Route 66 Vacation Packages

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Flight and hotel packages to Historic Route 66

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Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
per person
Jul 25 - Jul 28
Roundtrip non-stop flight included
Raleigh (RDU) to Springfield (SGF)
This smoke-free resort features 2 restaurants, 2 outdoor pools, and an indoor pool. Bring the family and enjoy the mini golf, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
Still Waters Resort

Still Waters Resort

4 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 28
Roundtrip non-stop flight included
Raleigh (RDU) to Springfield (SGF)
A marina, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free condo resort. Bring the family and enjoy the mini golf, children's pool, and free theme park shuttle. Enjoy the 2 spa tubs and perks like free self parking and free WiFi.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 4
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.

Top Historic Route 66 hotel deals

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $151 per night
$151
per night
May 28 - May 29
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.
Pet friendly
Breakfast available
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $151 per night
$151
per night
May 28 - May 29
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.
Breakfast available
Free WiFi
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $167 per night
$167
per night
May 27 - May 28
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Breakfast available
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $100 per night
$100
per night
May 27 - May 28
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking.
Pet friendly
Parking available
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
Free Cancellation
Reserve now, pay when you stay
The price is $49 per night
$49
per night
May 19 - May 20
A casino, 4 restaurants, and an outdoor pool are all featured at this resort. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Relax with a drink at one of the 4 bars/lounges and enjoy the gym.
Breakfast available
Pool
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $171 per night
$171
per night
May 27 - May 28
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Parking available
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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.

Popular places to visit in Historic Route 66

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier