
Historic Route 66 Holidays from £1,253
Book a Hotel + Flight or Car together to unlock savings
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Your Historic Route 66 Holiday
When adventure calls, answer it with a customised holiday package to Historic Route 66. Wherever it is you're going and whatever your plans are, get set to discover a destination with so much to offer. Why not organise your trip to Historic Route 66 around a few of its most popular cities? Virden, East Gillespie and Gillespie all make great places to start. Whether you're planning to travel on a shoestring or in the lap of luxury, Expedia are here to help you organise your next dream Historic Route 66 holiday.
Top Historic Route 66 Flight + Hotel Deals

Level Chicago Fulton Market
Reviewed on 14 Mar 2026

Hotel Riu Plaza Chicago
Reviewed on 22 Mar 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on 22 Mar 2026

LondonHouse Chicago, Curio Collection by Hilton
Reviewed on 18 Mar 2026
Historic Route 66 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Arcadia Lake and Flagstaff Convention and Visitors Bureau |
Top hotels in Historic Route 66

Congress Plaza Hotel
It’s an old hotel. It needs a quality paint job and new carpets in the hallways among many other things. But the lake view rooms makes up for a lot of what’s missing.
Reviewed on 22 Mar 2026

Hotel Riu Plaza Chicago
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with ...
Reviewed on 22 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
Spent three nights with husband and teenage son over spring break. Young man who checked us in was not friendly, did not mention happy hour, or breakfast. He did not give us any information except room number. Breakfast staff was nice and polite. Recommend getting to breakfast early or there will ...
Reviewed on 22 Mar 2026
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.











