Historic Route 66 flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Save 100% on your flight

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Westgate Branson Lakes Resort

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per person

Jul 25 - Jul 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Springfield (SGF)

This hotel features an outdoor pool and an indoor pool. There's fun for all ages with mini golf and a playground, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking.

Hotel Riu Plaza Chicago

Downtown Chicago

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per person

Aug 1 - Aug 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Sandia Resort And Casino

Northeast Heights

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per person

Aug 28 - Aug 31

found 14 hours ago

Roundtrip flight included

Houston (IAH) to Albuquerque (ABQ)

This smoke-free resort features a golf course, a casino, and a full-service spa. Enjoy a meal in one of the 5 restaurants and free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.

Four Points by Sheraton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

per person

Aug 3 - Aug 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and concierge services and wedding services are also offered.

Top Historic Route 66 hotels deals

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Free Cancellation

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This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

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This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

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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.

The Wade

644 N Lake Shore Dr, Chicago, IL

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

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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.