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 Wade
Downtown Chicago
Price was ￥455,390, price is now ￥353,707 per person
￥353,707
per person
Jul 15 - Jul 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,834 reviews)
The bathroom door is sliding and does not close completely and the extractor does not work. Excellent location, valet parking somewhat disorganized, staff 3.5/5 of kindness.
Reviewed on May 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥548,170, price is now ￥435,320 per person
￥435,320
per person
Jul 15 - Jul 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
The view from our room was awesome!!
Reviewed on May 27, 2026
The Emily Hotel
Downtown Chicago
Price was ￥565,608, price is now ￥456,772 per person
￥456,772
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,322 reviews)
Great vibes and it’s perfectly located to enjoy the west loop.
Reviewed on May 26, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥444,254, price is now ￥365,090 per person
￥365,090
per person
Jul 15 - Jul 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Great hotel. Loved the lobby and our room. Would definitely stay here again.
Reviewed on May 19, 2026
The Langham, Chicago
Downtown Chicago
Price was ￥566,982, price is now ￥473,232 per person
￥473,232
per person
Jul 15 - Jul 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
10/10 experience! Love this hotel!…the only negative was a less than nice /helpful staff person at the front desk of the spa when I asked about the use of the sauna/steam room and also my neighbors next to my room were quite loud
Reviewed on May 27, 2026
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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
Price was ￥741,610, price is now ￥574,700 per person
￥574,700
per person
Aug 8 - Aug 15
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
The view from our room was awesome!!
Reviewed on May 27, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥797,444, price is now ￥649,737 per person
￥649,737
per person
Aug 8 - Aug 15
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
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View all trips3 Night Mountain vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥356,926, price is now ￥291,502 per person
￥291,502
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
The staff is very helpful, always ready to answer any question about the hotel or about the city of Chicago. The hotel is very clean , the breakfast is very good with many choices and the staff in the restaurant is excellent.
My wife and I stayed in that place for eight days and seven nights and we are very happy to be there.
Also the hotel is in a very good location very close to some of the most important places of Chicago.
If you want to visit the beautiful city of Chicago do not miss the opportunity to know this hotel.
Reviewed on May 27, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥374,152, price is now ￥302,189 per person
￥302,189
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice.
Reviewed on May 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥449,300, price is now ￥369,966 per person
￥369,966
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
The view from our room was awesome!!
Reviewed on May 27, 2026
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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.
WorldMark Grand Lake
Price was ￥369,524, price is now ￥351,806 per person
￥351,806
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tulsa (TUL)
9.6/10 Exceptional! (129 reviews)
It was everything we needed to celebrate our granddaughter’s graduation.
I felt at home and will be back again.
Reviewed on May 24, 2026
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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.
