Historic Route 66 Vacations from ￥48,177
Book a Hotel + Flight or Car together to unlock savings
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Save up to ￥45,448 when you book a flight and hotel together*
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The Latest Historic Route 66 Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥75,300, price is now ￥49,737 per person
￥49,737
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
It is clean and close to cicty center
Reviewed on Sep 30, 2025
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was ￥111,061, price is now ￥75,466 per person
￥75,466
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
Best place to stay when facing an early morning flight!
Reviewed on Oct 1, 2025
Hilton Orrington / Evanston
Downtown Evanston
Price was ￥78,318, price is now ￥53,499 per person
￥53,499
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
7.6/10 Good! (1,007 reviews)
Two mornings received poor service at breakfast.
King bed in room. Could not open cabinet
Reviewed on Sep 15, 2025
Hilton Rosemont Chicago O'Hare
O'Hare
Save 100% on your flight
Price was ￥166,686, price is now ￥120,004 per person
￥120,004
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.6/10 Excellent! (1,006 reviews)
Close to CTA station. Walkong distance to several restaraunts.
Reviewed on Sep 28, 2025
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
The price is ￥19,339 per night from Oct 30 to Oct 31
￥19,339
￥22,704 total
Oct 30 - Oct 31
includes taxes & fees
8.6/10 Excellent! (3,388 reviews)
First time to Chicago
"Excellent location! Quick walk to the train, and centrally located to walk every where we wanted to visit. Adrian greeted us upon arrival and made us feel like we were coming home! Not just upon arrival but every time we stepped into the lobby! Her kindness and welcoming persona was felt by all! ..."
Reviewed on Sep 30, 2025
Central Loop Hotel
111 West Adams Street, Chicago, IL
The price is ￥26,478 per night from Oct 5 to Oct 6
￥26,478
￥31,081 total
Oct 5 - Oct 6
includes taxes & fees
8.4/10 Very Good! (1,878 reviews)
"Loved everything about it. Will definitely stay again in the future."
Reviewed on Sep 30, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,864 per night from Oct 2 to Oct 3
￥22,864
￥26,840 total
Oct 2 - Oct 3
includes taxes & fees
7.8/10 Good! (9,387 reviews)
"Top Lage, sehr zentral"
Reviewed on Oct 1, 2025
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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