Historic Route 66 Pet-friendly Vacations
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Top Pet-friendly 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 ￥382,160, price is now ￥307,376 per person
￥307,376
per person
May 14 - May 17
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Great experience and friendly staff
Reviewed on Apr 6, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥754,171, price is now ￥611,128 per person
￥611,128
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
The Thompson Chicago is a wonderful boutique Hotel located in the perfect part of the city.
Reviewed on Apr 6, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥394,250, price is now ￥329,920 per person
￥329,920
per person
May 14 - May 17
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,503 reviews)
Overall really clean I just wish they had room service, and the TVs had access to Netflix atleast.
Reviewed on Apr 6, 2026
Warwick Allerton - Chicago
Downtown Chicago
Price was ￥385,252, price is now ￥323,645 per person
￥323,645
per person
May 14 - May 17
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (3,032 reviews)
A beautiful historic hotel...we very much enjoyed our stay there.
Reviewed on Mar 31, 2026
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View all trips5* Pet-friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥412,786, price is now ￥371,364 per person
￥371,364
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥1,074,774, price is now ￥1,048,675 per person
￥1,048,675
per person
May 29 - May 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Enjoyed a very comfortable stay.
Reviewed on Mar 30, 2026
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View all trips3 Night Pet-friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥394,250, price is now ￥312,527 per person
￥312,527
per person
May 14 - May 17
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.
Reviewed on Apr 4, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥404,794, price is now ￥325,539 per person
￥325,539
per person
May 14 - May 17
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Great location. Staff was welcoming. Room could have been cleaned better hair on sink, toilet and bed but overall not the worse I’ve seen. Would stay again for sure.
Reviewed on Apr 5, 2026
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View all trips4 Night Pet-friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥1,079,368, price is now ￥956,661 per person
￥956,661
per person
May 29 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Great location. Staff was welcoming. Room could have been cleaned better hair on sink, toilet and bed but overall not the worse I’ve seen. Would stay again for sure.
Reviewed on Apr 5, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥1,111,450, price is now ￥970,464 per person
￥970,464
per person
May 29 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
I enjoyed this property and the view is top notch
Reviewed on Apr 6, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥1,072,628, price is now ￥966,250 per person
￥966,250
per person
May 29 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.
Reviewed on Apr 6, 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.
