Central Chicago Pet-friendly Vacations
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Top Pet-friendly vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥454,488, price is now ￥361,036 per person
￥361,036
per person
May 1 - May 6
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon
Reviewed on Mar 29, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥408,952, price is now ￥326,052 per person
￥326,052
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing
Reviewed on Mar 27, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥491,402, price is now ￥394,486 per person
￥394,486
per person
Jun 4 - Jun 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
My husband and I stayed in the presidential suite. It was absolutely spectacular. Wonderful food at prime Ocean and good breakfast. Amenities were out of this world. Customer service was amazing. We met the best bartender ever at the rooftop bar. The views were the best in Chicago!! highly recommend this hotel.
Reviewed on Mar 31, 2026
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View all trips5* Pet-friendly vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥483,150, price is now ￥395,209 per person
￥395,209
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Quality staff and the property was well appointed
Reviewed on Mar 30, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥458,142, price is now ￥430,439 per person
￥430,439
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
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View all trips3 Night Pet-friendly vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥395,386, price is now ￥337,268 per person
￥337,268
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Breakfast was delish! Staff was nice..great location.
Reviewed on Mar 31, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥513,756, price is now ￥438,043 per person
￥438,043
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Quality staff and the property was well appointed
Reviewed on Mar 30, 2026
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View all trips4 Night Pet-friendly vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel
Downtown Chicago
Price was ￥425,648, price is now ￥380,130 per person
￥380,130
per person
Jun 4 - Jun 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Price was great. Room was huge with such a beautiful view of the city. Also a safe location within walking distance of things to see and do
Reviewed on Mar 5, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥491,402, price is now ￥394,486 per person
￥394,486
per person
Jun 4 - Jun 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
My husband and I stayed in the presidential suite. It was absolutely spectacular. Wonderful food at prime Ocean and good breakfast. Amenities were out of this world. Customer service was amazing. We met the best bartender ever at the rooftop bar. The views were the best in Chicago!! highly recommend this hotel.
Reviewed on Mar 31, 2026
Pendry Chicago
Downtown Chicago
Price was ￥462,616, price is now ￥416,814 per person
￥416,814
per person
Jun 4 - Jun 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back.
Reviewed on Mar 23, 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.
