Historic Route 66 Ski Vacations
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Top Ski vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥1,093,078, price is now ￥764,910 per person
￥764,910
per person
Aug 8 - Aug 13
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Our room this time was more cozy (re: small). Bathroom was efficient (re: cramped). I would guess they took a suite and made an extra room of it. Staff was great, hotel clean. Just a bad draw in the room - we arrived late.
Reviewed on Jun 27, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥1,158,944, price is now ￥801,909 per person
￥801,909
per person
Aug 8 - Aug 13
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Great location and stay. Will stay again next time in Chicago.
Reviewed on Jun 28, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥1,200,320, price is now ￥837,176 per person
￥837,176
per person
Aug 8 - Aug 13
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
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View all trips5* Ski 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 ￥455,368, price is now ￥388,928 per person
￥388,928
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥491,901, price is now ￥444,328 per person
￥444,328
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Amazing the staff was so friendly. The hotel is just I can’t believe I never stayed at this hotel. This is by far my top five hotels I will definitely be returning. Thank you so much for such a wonderful stay
Kimberly Chardukian
Reviewed on Jun 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥463,062, price is now ￥457,214 per person
￥457,214
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
We had a lovely 2 night stay in Chicago and the room with lake view was superb with lovely touches by the cleaning staff who made the stay very special
Reviewed on Jun 1, 2026
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View all trips3 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥372,353, price is now ￥316,212 per person
￥316,212
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Great location and stay. Will stay again next time in Chicago.
Reviewed on Jun 28, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥455,368, price is now ￥388,928 per person
￥388,928
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips4 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥379,384, price is now ￥309,758 per person
￥309,758
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Great location and stay. Will stay again next time in Chicago.
Reviewed on Jun 28, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥514,854, price is now ￥440,845 per person
￥440,845
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
