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
Save 100% on your flight
Price was ￥336,284, price is now ￥236,733 per person
￥236,733
per person
Aug 1 - Aug 8
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,361 reviews)
This is our favorite hotel in chicago. Great location and staff. Rooms very comfortable.
Reviewed on May 11, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥551,352, price is now ￥397,630 per person
￥397,630
per person
Jun 15 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on May 13, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥538,023, price is now ￥410,128 per person
￥410,128
per person
Jul 19 - Jul 25
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Wonderful experience, beautiful place. Breakfast on site was a huge plus!
Reviewed on May 13, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥704,418, price is now ￥544,220 per person
￥544,220
per person
Jul 19 - Jul 25
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 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 Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥620,061, price is now ￥516,742 per person
￥516,742
per person
Aug 1 - Aug 8
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Loved our suite- gorgeous views! Great service and excellent location
Reviewed on May 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥704,418, price is now ￥544,220 per person
￥544,220
per person
Jul 19 - Jul 25
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 2026
Don't see what you're looking for?
See all available trips from Vancouver 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.
