Historic Route 66 Beach Vacations
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Top Beach vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥659,915, price is now ￥426,058 per person
￥426,058
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Clean rooms, friendly staff.
Reviewed on Mar 13, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥560,889, price is now ￥424,265 per person
￥424,265
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026
Hilton Chicago
Downtown Chicago
Price was ￥605,910, price is now ￥499,852 per person
￥499,852
per person
May 28 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,658 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on Mar 12, 2026
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View all trips5* Beach vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel St Louis
Downtown St. Louis
Price was ￥500,924, price is now ￥486,718 per person
￥486,718
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to St. Louis (STL)
9.4/10 Exceptional! (1,001 reviews)
Beautiful accommodations. Attentive and genuine staff. We felt like celebrities. Beyond first class service!!
Reviewed on Feb 23, 2026
The Ritz-Carlton, St. Louis
Clayton
Price was ￥574,842, price is now ￥567,143 per person
￥567,143
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to St. Louis (STL)
9.2/10 Wonderful! (557 reviews)
Excellent hotel with various restaurants and expansive lobby area.. staff very attentive.
Reviewed on Feb 6, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips3 Night Beach vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥465,726, price is now ￥372,726 per person
￥372,726
per person
May 29 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 2026
Level Chicago - River North
Downtown Chicago
Price was ￥452,740, price is now ￥368,338 per person
￥368,338
per person
May 29 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (858 reviews)
I would stay here again without a second thought. Great
Reviewed on Mar 11, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips4 Night Beach vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥528,000, price is now ￥412,964 per person
￥412,964
per person
May 28 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 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.
