
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.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥211,851, price is now ¥168,581 per person
¥168,581
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥313,513, price is now ¥224,654 per person
¥224,654
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

The Emily Hotel
Downtown Chicago
Price was ¥230,676, price is now ¥179,926 per person
¥179,926
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025

Level Chicago - River North
Downtown Chicago
Price was ¥218,872, price is now ¥174,100 per person
¥174,100
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 2025

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View all trips5* Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥313,513, price is now ¥224,654 per person
¥224,654
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥1,253,017, price is now ¥1,111,188 per person
¥1,111,188
per person
Nov 22 - Nov 28
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
My wife and I spent an incredibly enjoyable weekend at the hotel. It is within walking distance to many different points of interest in the heart of the Magnificent Mile. The service, amenities, and stay were memorable. We will definitely return.
Reviewed on Sep 29, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥1,300,753, price is now ¥1,173,353 per person
¥1,173,353
per person
Nov 22 - Nov 28
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Excellent hotel, my only complaint would be the Peninsula food service.
We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster.
As to the main dining room the service continues, as always, to be erratic and frequently slow. Food is sometimes served hot, sometimes not.
The room service on our checkout day was absolutely abysmal. We both ordered eggs Benedict and both orders were served not a degree above room temperature. The hollandaise sauce was so cold it had solidified.
There really is no excuse for this.
And unfortunately we did not have time to return the order as we had a plane to catch and we were running a bit behind.
For an otherwise professional hotel the food service and quality is sadly lacking. It leads one to believe that the F&B manager could be a nephew, a cousin, or some other family member need of a job.
Reviewed on Sep 27, 2025
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View all trips3 Night Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North
Downtown Chicago
Price was ¥218,872, price is now ¥174,100 per person
¥174,100
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥313,513, price is now ¥224,654 per person
¥224,654
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

The Emily Hotel
Downtown Chicago
Price was ¥230,676, price is now ¥179,926 per person
¥179,926
per person
Nov 1 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025
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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 Riu Plaza Chicago
Downtown Chicago
Price was ¥321,722, price is now ¥261,166 per person
¥261,166
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
The stay was fine. The lobby area is very nice so one feels one is in a 4 or 5 star hotel. I would come back to stay again. The breakfast was good, a lot of different foods. Inside the room was very clean and seemed new.
Reviewed on Sep 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥497,763, price is now ¥379,929 per person
¥379,929
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

The Emily Hotel
Downtown Chicago
Price was ¥356,734, price is now ¥288,542 per person
¥288,542
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 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.