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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥542,266, price is now ￥421,644 per person
￥421,644
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The room was very small for 4 people. It has pull-out coach for 2 people and in reality one person sleeps comfortably. It is not for two people.
Reviewed on Jul 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥716,212, price is now ￥560,173 per person
￥560,173
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥606,160, price is now ￥477,030 per person
￥477,030
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great experience would book again
Reviewed on Jul 4, 2026
Omni Chicago Hotel
Downtown Chicago
Price was ￥560,823, price is now ￥445,210 per person
￥445,210
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!
Reviewed on Jul 4, 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, St. Louis
Clayton
Price was ￥518,810, price is now ￥518,810 per person
￥518,810
per person
Aug 10 - Aug 14
found 3 hours ago
Roundtrip flight included
Osaka (KIX) to St. Louis (STL)
9.2/10 Wonderful! (570 reviews)
Very nice property to stay at and a nice walk to Shaw Park.
Reviewed on Jun 28, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥716,212, price is now ￥560,173 per person
￥560,173
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was ￥740,956, price is now ￥625,204 per person
￥625,204
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.
Reviewed on Jul 2, 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.
Nobu Hotel Chicago
Downtown Chicago
Price was ￥462,314, price is now ￥404,850 per person
￥404,850
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.
Reviewed on Jul 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥580,704, price is now ￥522,144 per person
￥522,144
per person
Aug 8 - Aug 11
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips4 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ￥393,212, price is now ￥333,220 per person
￥333,220
per person
Aug 19 - Aug 23
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!
Reviewed on Jul 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥513,962, price is now ￥426,949 per person
￥426,949
per person
Aug 19 - Aug 23
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 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.
