
Southern Wisconsin Beach Vacations
Book a Beach Hotel + Flight or Car together to unlock savings
Photo by Evae
- Plan, book, travel with confidence
- Better togetherSave up to ¥109,000 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 Beach vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥413,758, price is now ¥340,688 per person
¥340,688
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Queen is very small but nice staff
Reviewed on Jul 16, 2026


Level Chicago – Old Town
Downtown Chicago
Price was ¥467,276, price is now ¥379,566 per person
¥379,566
per person
Aug 25 - Aug 29
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥457,188, price is now ¥381,469 per person
¥381,469
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
I love all about this hotel
Reviewed on Jul 15, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* Beach vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Nobu Hotel Chicago
Downtown Chicago
Price was ¥496,798, price is now ¥429,980 per person
¥429,980
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026


The Peninsula Chicago
Downtown Chicago
Price was ¥596,326, price is now ¥548,261 per person
¥548,261
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
Who said you can’t work and play at the same time? Certainly not me.
Chicago is a city that feels like home, no matter how much time passes. This trip has been all about balance... blending high-level work with the kind of downtime only The Peninsula can provide. It’s been a perfect backdrop for reflecting on my time living in the iconic Marina City "corncob" towers; they remain a meaningful piece of my own history.
Chicago is a city of food, and I’m tipping my hat to the spots that never miss. The Peninsula is at the top of that list: Egg Benedict and the best service team every morning, and drinks at the Z Bar (Tim and Krystal are absolute gems). When we step out, our favorites remain a consistent rotation: Smith & Wollensky, Gibsons, Rosebud, and NoMi, but it doesn't stop there. If you need advice, the concierge staff are phenomenal. Lastly, a special shout-out to housekeeping; they not only kept us organized but were incredibly attentive. We are very grateful.
Simply put: The Peninsula knows how to pamper you. They are consistent, classic, and always worth the stay. Perfection in motion.
Reviewed on Jul 13, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Beach vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥413,758, price is now ¥340,688 per person
¥340,688
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Queen is very small but nice staff
Reviewed on Jul 16, 2026


Level Chicago – Old Town
Downtown Chicago
Price was ¥467,276, price is now ¥379,566 per person
¥379,566
per person
Aug 25 - Aug 29
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 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.
