Historic Route 66 Holidays from £1,253

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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

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Hotel Riu Plaza Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
Kinzie Hotel

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

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £92 per night from 1 Apr to 2 Apr
£92
1 Apr - 2 Apr
includes taxes & fees
8/10 Very Good! (9,982 reviews)
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

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £137 per night from 6 Apr to 7 Apr
£137
6 Apr - 7 Apr
includes taxes & fees
9.4/10 Exceptional! (3,590 reviews)
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

Hotel Riu Plaza Chicago
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
Fully refundableReserve now, pay when you stay
The price is £115 per night from 29 Mar to 30 Mar
£115
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (5,765 reviews)
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

Embassy Suites by Hilton Chicago Downtown River North
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.

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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.