Historic Route 66 Romantic Vacations
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Top Romantic vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
￥314,167
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
Great hotel. Great food. Clean rooms. Area of the hotel felt safe and very close to many others attractions nearby.
Reviewed on Oct 5, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
￥301,820
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
Fantastic hotel! Really nice, clean, staff was incredibly friendly. We got the Fairmont gold room edition and it was totally worth it having food and drinks available during the day. We ate breakfast there each morning and it was great! Would definitely stay here again Next time we come to visit.
Reviewed on Oct 5, 2026
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View all trips5* Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
￥577,532
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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View all trips3 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
￥512,146
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
The rooms are very small ,the pictures and videos is what sells the hotel for sure. Disappointed with the stay and the amount I was charged
Reviewed on Oct 4, 2026
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View all trips4 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
