
Historic Route 66 Mountain Vacations
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Top Mountain vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥272,410, price is now ¥188,740 per person
¥188,740
per person
Nov 12 - Nov 18
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Nice hotel but room was extremely small.
Reviewed on Sep 11, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥460,254, price is now ¥301,832 per person
¥301,832
per person
Nov 12 - Nov 18
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Great bar on the 16th floor. Staff was great
Reviewed on Sep 10, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥314,632, price is now ¥221,254 per person
¥221,254
per person
Nov 12 - Nov 18
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
Rooms are very clean and staff was great
Reviewed on Sep 11, 2025

Pendry Chicago
Downtown Chicago
Price was ¥321,014, price is now ¥236,332 per person
¥236,332
per person
Nov 12 - Nov 18
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on Sep 8, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥282,136, price is now ¥210,421 per person
¥210,421
per person
Nov 12 - Nov 18
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 2025
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View all trips5* Mountain vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥460,254, price is now ¥301,832 per person
¥301,832
per person
Nov 12 - Nov 18
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Great bar on the 16th floor. Staff was great
Reviewed on Sep 10, 2025

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View all trips4 Night Mountain vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Highlands Resort at Verde Ridge
Verde Santa Fe
Price was ¥222,336, price is now ¥205,026 per person
¥205,026
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Sedona (SDX)
9.4/10 Exceptional! (1,103 reviews)
Room was upstairs with no elevator. Room itself was very nice with full kitchen, dining, living room bedroom and very nice sized bath with plenty of towels. Balcony had table and chairs and a nice view. Unfortunately pool deck was under construction with lots of dust and noise. On-site free laundry was convenient. Our room keys quit working the third afternoon but they brought us new ones. We would recommend. Pool construction will end soon then it will be a 10
Reviewed on Sep 9, 2025

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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.