Historic Route 66 Holidays from £807
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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.
Swissotel - Chicago
Downtown Chicago
Price was £1,100, price is now £807 per person
£807
per person
18 Jun - 21 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on 6 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,325, price is now £977 per person
£977
per person
18 Jun - 21 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking
Reviewed on 3 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,499, price is now £1,124 per person
£1,124
per person
18 Jun - 21 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything
Reviewed on 4 May 2026
Kinzie Hotel
Downtown Chicago
Price was £1,902, price is now £1,433 per person
£1,433
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,099 reviews)
The staff was super friendly. The location was perfect and the room was very comfortable and clean.
Reviewed on 4 May 2026
The Wade
Downtown Chicago
Price was £1,686, price is now £1,271 per person
£1,271
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,814 reviews)
The Breakfast could've been better.. Wasn't very good for the price I paid.
Reviewed on 1 May 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
Central Loop Hotel
111 West Adams Street Chicago IL
The price is £107 per night from 25 May to 26 May
£107
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (2,114 reviews)
Everything was great
Reviewed on 6 May 2026
The Aquarius Casino Resort, BW Premier Collection
1900 S Casino Dr Laughlin NV
Fully refundableReserve now, pay when you stay
The price is £51 per night from 13 May to 14 May
£51
13 May - 14 May
includes taxes & fees
8.2/10 Very Good! (7,536 reviews)
Great overall experience. The proximity to the river, stores, dining venues and other hotels was awesome. Since we went up for a wrestling tournament at the auto field house, the 15min drive there wasn't bad.
Reviewed on 6 May 2026
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
The price is £99 per night from 25 May to 26 May
£99
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,683 reviews)
Friendly staff. Good location
Reviewed on 5 May 2026
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.
