
Southern Wisconsin Cheap Vacations
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Top Cheap 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 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Staff was friendly and helpful. Great value for price we paid.
Reviewed on Jul 15, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥520,328, price is now ¥420,151 per person
¥420,151
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Free beer no perfect everyone was great
Reviewed on Jul 15, 2026


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥516,279, price is now ¥430,770 per person
¥430,770
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk.
It took us a little while to figure out all the lighting but that was a small thing.
The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good!
All in all, a very happy experience.
Reviewed on Jul 14, 2026

Level Chicago - River North
Downtown Chicago
Price was ¥438,092, price is now ¥373,984 per person
¥373,984
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Holes in the carpeting in living room. Door that enters unit doesn’t close without slamming it. Looks like wear and tear since we were there before.
Reviewed on Jul 14, 2026
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View all trips5* Cheap 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 12 hours 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

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥516,279, price is now ¥430,770 per person
¥430,770
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk.
It took us a little while to figure out all the lighting but that was a small thing.
The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good!
All in all, a very happy experience.
Reviewed on Jul 14, 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 12 hours 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
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View all trips4 Night Cheap 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 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Staff was friendly and helpful. Great value for price we paid.
Reviewed on Jul 15, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥520,328, price is now ¥420,151 per person
¥420,151
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Free beer no perfect everyone was great
Reviewed on Jul 15, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥516,279, price is now ¥430,770 per person
¥430,770
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk.
It took us a little while to figure out all the lighting but that was a small thing.
The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good!
All in all, a very happy experience.
Reviewed on Jul 14, 2026
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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.
