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

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥453,524, price is now ¥272,138 per person
¥272,138
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
I had a really great stay at Hotel Riu Plaza Chicago overall. The location was honestly one of the best parts, it’s perfectly situated and close to so many attractions, restaurants, and things to do. Everything I planned during my trip was within easy reach, which made getting around super convenient and stress-free.
The room was clean, comfortable, and well-maintained, and the overall atmosphere of the hotel felt modern and welcoming. The staff was also pleasant and helpful throughout my stay.
If I had to rate the breakfast, I’d say it was mid, not bad, but nothing particularly memorable. It got the job done, but it wasn’t a highlight of the experience.
That said, the stay itself was great, and I truly enjoyed my time there. I’d definitely recommend it, especially if you’re looking for a hotel in a prime Chicago location.
Reviewed on Feb 20, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥399,936, price is now ¥293,079 per person
¥293,079
per person
May 1 - May 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥494,822, price is now ¥365,182 per person
¥365,182
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥393,963, price is now ¥294,424 per person
¥294,424
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥400,475, price is now ¥304,811 per person
¥304,811
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
The location and views were the best!
Reviewed on Feb 18, 2026
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View all trips5* Adventure vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥494,822, price is now ¥365,182 per person
¥365,182
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥496,748, price is now ¥378,294 per person
¥378,294
per person
May 1 - May 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥587,878, price is now ¥471,300 per person
¥471,300
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The room was comfortable and beautiful design. Comfortable bed and bedding. Large desk. Good walkable location. But we could hear sirens at night
Reviewed on Feb 16, 2026
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View all trips3 Night Adventure vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥373,341, price is now ¥278,734 per person
¥278,734
per person
May 13 - May 16
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
I had a really great stay at Hotel Riu Plaza Chicago overall. The location was honestly one of the best parts, it’s perfectly situated and close to so many attractions, restaurants, and things to do. Everything I planned during my trip was within easy reach, which made getting around super convenient and stress-free.
The room was clean, comfortable, and well-maintained, and the overall atmosphere of the hotel felt modern and welcoming. The staff was also pleasant and helpful throughout my stay.
If I had to rate the breakfast, I’d say it was mid, not bad, but nothing particularly memorable. It got the job done, but it wasn’t a highlight of the experience.
That said, the stay itself was great, and I truly enjoyed my time there. I’d definitely recommend it, especially if you’re looking for a hotel in a prime Chicago location.
Reviewed on Feb 20, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥346,104, price is now ¥295,819 per person
¥295,819
per person
May 13 - May 16
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026

Arlo Chicago
Downtown Chicago
Price was ¥348,052, price is now ¥299,496 per person
¥299,496
per person
May 13 - May 16
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Updated, modern clean hotel that smelled good! Great service!
Reviewed on Feb 20, 2026
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View all trips4 Night Adventure vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

The Iron Horse Hotel
Fifth Ward
Price was ¥402,854, price is now ¥373,624 per person
¥373,624
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Nice community seating areas . Fun pool table at the bar. All night valet. Clean comfortable room.
Reviewed on Feb 15, 2026


The Pfister Hotel
Downtown Milwaukee
Price was ¥433,257, price is now ¥398,860 per person
¥398,860
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Milwaukee (MKE)
9.6/10 Exceptional! (1,786 reviews)
Staff was great & extremely responsive. The property was very cool & we look forward to staying again!
Reviewed on Feb 19, 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.
