
Southern Wisconsin Pet-friendly Vacations
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Top Pet-friendly vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Downtown Chicago
Price was ¥201,130, price is now ¥161,431 per person
¥161,431
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,034 reviews)
The theme and room were amazing. CheckIn at 3AM was the smoothest with the kindest staff. I was so comfortable and did not want to leave such a lovely space! Can’t wait to stay here again, sincerely! Thank you!
Reviewed on Sep 8, 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥391,765, price is now ¥264,080 per person
¥264,080
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025

Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was ¥278,320, price is now ¥223,338 per person
¥223,338
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (132 reviews)
My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced.
Reviewed on Sep 5, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥291,130, price is now ¥243,804 per person
¥243,804
per person
Nov 20 - Nov 24
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 2025

Pendry Chicago
Downtown Chicago
Price was ¥244,828, price is now ¥206,978 per person
¥206,978
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on Sep 8, 2025
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Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥391,765, price is now ¥264,080 per person
¥264,080
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥533,264, price is now ¥326,389 per person
¥326,389
per person
Dec 1 - Dec 3
found 5 hours ago
Roundtrip flight included
Kagoshima (KOJ) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on Sep 8, 2025

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View all trips4 Night Pet-friendly vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥306,856, price is now ¥238,872 per person
¥238,872
per person
Nov 20 - Nov 24
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
Very clean, nice smelling, good breakfast and good customer service
Reviewed on Sep 8, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥409,760, price is now ¥304,676 per person
¥304,676
per person
Nov 20 - Nov 24
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on Sep 8, 2025

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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.