
Southern Wisconsin Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
Photo by Evae
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Pet-friendly vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was ¥495,657, price is now ¥368,190 per person
¥368,190
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (414 reviews)
This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back.
Reviewed on Mar 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥640,345, price is now ¥417,190 per person
¥417,190
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)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.
Reviewed on Mar 9, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥624,805, price is now ¥463,414 per person
¥463,414
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
My stay at LondonHouse Chicago was absolutely amazing from start to finish. The hotel itself is beautiful and perfectly located, offering stunning views of the river and city skyline.
The restaurants were excellent, with delicious food and a great atmosphere. The rooftop experience was definitely a highlight and made the stay feel even more special.
I also had the chance to visit the spa, which was incredibly relaxing and well done. The environment was peaceful, the service was top-tier, and it was the perfect way to unwind during my trip.
Overall, everything—from the service to the amenities—was exceptional. I would definitely book again and highly recommend LondonHouse Chicago to anyone visiting the city. ⭐⭐⭐⭐⭐
Reviewed on Mar 10, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥653,618, price is now ¥488,172 per person
¥488,172
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at
Reviewed on Mar 10, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥573,854, price is now ¥430,932 per person
¥430,932
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Hotel had amazing views in the panaromic room. The other issue doe me was not having a shower door in the actual shower which made the shower not so warm. The shower head was either in the top of the shower or hand-held which made it a little uncomfortable but other than that this property views are amazing with beautifully decorated lobby and other floors were decorated beautifully.
Reviewed on Mar 10, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* Pet-friendly vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥653,618, price is now ¥488,172 per person
¥488,172
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at
Reviewed on Mar 10, 2026

Four Seasons Hotel Chicago
Downtown Chicago
Price was ¥757,635, price is now ¥657,312 per person
¥657,312
per person
May 28 - Jun 2
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Staff is incredible. Bartenders in lobby bar are phenomenal!!
Reviewed on Mar 9, 2026

The St. Regis Chicago
Downtown Chicago
Price was ¥730,948, price is now ¥684,891 per person
¥684,891
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (98 reviews)
My stay at the St. Regis Chicago was truly a beautiful and memorable luxury experience.
From the moment I arrived, the property immediately made an impression. The atmosphere is polished, calm, and intentional in a way that lets you know you are somewhere special. The design of the hotel is stunning, the rooms are beautifully done, the views are breathtaking, and there is a softness to the experience that makes you slow down and really appreciate the details. It is the kind of place where you naturally pause and take everything in.
One thing I always say is that luxury is not only about beautiful spaces. Of course the architecture, the rooms, and the views matter and the St. Regis absolutely delivers on all of that. But to me, true luxury is also about how people make you feel. The check-in and the checkout may seem like small parts of a stay, but they are actually the first impression and the last impression, and those moments matter just as much as the property itself.
I also want to acknowledge Alyssa and manager Richard. After speaking with them, I genuinely appreciated the professionalism, attentiveness, and willingness to listen. Richard in particular created space for a clear and respectful conversation, and I value that greatly. Sometimes what leaves the biggest impression is not perfection, but how a team responds with care, grace, and a desire to make sure a guest leaves feeling heard. That level of hospitality reflects well on the brand.
Reviewed on Mar 9, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips3 Night Pet-friendly vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ¥291,649, price is now ¥254,502 per person
¥254,502
per person
May 4 - May 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥360,232, price is now ¥275,371 per person
¥275,371
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.
Reviewed on Mar 9, 2026

The Godfrey Hotel Chicago
Downtown Chicago
Price was ¥307,418, price is now ¥255,935 per person
¥255,935
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,060 reviews)
I’d give this hotel an 9 out of 10. Overall, it was a really good stay and I’d definitely consider coming back. The room was clean, comfortable, and well-maintained. The bed was cozy, and everything looked neat and organized when we arrived. The staff was friendly and helpful, which made the check-in and check-out process smooth and easy. I do feel like there should be microwaves inside these rooms. Still, overall it was a great experience. Clean rooms, nice staff, and a comfortable stay. Solid 9/10. I’d recommend it to anyone looking for a reliable place to stay.
Reviewed on Mar 9, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Pet-friendly vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Embassy Suites by Hilton Chicago O'Hare Rosemont
Price was ¥361,562, price is now ¥321,902 per person
¥321,902
per person
May 15 - May 19
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,289 reviews)
Nice clean big rooms and the staff was great!
Reviewed on Mar 9, 2026

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ¥387,652, price is now ¥336,015 per person
¥336,015
per person
May 15 - May 19
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
