Southern Wisconsin Vacations from ￥316,657

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The Latest Southern Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was ￥357,911, price is now ￥316,657 per person
￥316,657
per person
Jul 1 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,252 reviews)
The parking was a little expensive

Reviewed on May 28, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ￥491,548, price is now ￥413,830 per person
￥413,830
per person
Jul 1 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
10/10 experience! Love this hotel!…the only negative was a less than nice /helpful staff person at the front desk of the spa when I asked about the use of the sauna/steam room and also my neighbors next to my room were quite loud

Reviewed on May 27, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥397,201, price is now ￥340,096 per person
￥340,096
per person
Jul 1 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Great hotel. Loved the lobby and our room. Would definitely stay here again.

Reviewed on May 19, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥588,458, price is now ￥507,032 per person
￥507,032
per person
Jul 1 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Everyone was so helpful and friendly Great environment. Cleaning, room service ,breakfast A+

Reviewed on May 29, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥370,218, price is now ￥325,702 per person
￥325,702
per person
Jul 1 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,405 reviews)
Shea was wondering! A couple of hiccups but she handled with ease. I would definitely stay again because of the service I received.

Reviewed on May 27, 2026

Where to stay in Southern Wisconsin

Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern Wisconsin
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

Find hotels in Downtown Milwaukee

Find the Best Southern Wisconsin Vacation Packages

Southern Wisconsin Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is ￥19,925 per night from Jun 14 to Jun 15
￥19,925
￥23,013 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (3,801 reviews)
"There were 2 beds in my room and one had 2 clips (for box spring) that were sticking out about 6” from floor. They would have ripped my leg open had I not had jeans on. My room was 305 right next to the elevators that dinged constantly all night!"

Reviewed on May 31, 2026

The Madison Concourse Hotel and Governor's Club
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
The price is ￥11,944 per night from Jun 3 to Jun 4
￥11,944
￥13,406 total
Jun 3 - Jun 4
includes taxes & fees
7/10 Good! (2,786 reviews)
"The hallway right outside of my room was very dirty. Trash and a cap to a water bottle sat there for about 2 days before it was cleaned up. The room was nice and slept great. Didn’t really ever hear anyone else down the hallways."

Reviewed on May 31, 2026

Mt. Olympus Water & Theme Park Resort
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is ￥23,652 per night from Jun 2 to Jun 3
￥23,652
￥27,886 total
Jun 2 - Jun 3
includes taxes & fees
9.2/10 Wonderful! (1,503 reviews)
"Gorgeous hotel and rooms were very nice!!"

Reviewed on May 30, 2026

Potawatomi Hotel & Casino
See all 7,516 properties in Southern Wisconsin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Southern Wisconsin

University of Wisconsin-Madison

University of Wisconsin-Madison

4.5/5(895 reviews)

Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Slidewheel water at a water park.

Mt. Olympus Water and Theme Park

3.5/5(148 reviews)

Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

Mt. Olympus Water and Theme Park
Historic Arched Entry to Camp Randall Stadium

Camp Randall Stadium

4.5/5(313 reviews)

Catch an event at Camp Randall Stadium during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Camp Randall Stadium

Frequently asked questions

Can I cancel my flight booking to Southern Wisconsin due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for almost every travel question, including about flight changes related to COVID-19. For more peace of mind, we recommend looking over the terms and conditions of your airfare before booking a seat.
What's the best way to find cheap flights to Southern Wisconsin that have flexible change policies?
By using our clever "No change fee" filter, that's how. All you have to do is enter your preferred dates and destination, click "Search," then click the checkbox directly under the "Flexible change policies" heading (it's on the left of your screen). Expedia makes it a snap to find inexpensive, flexible tickets to Southern Wisconsin.
What are some of the general tips for travelers to Southern Wisconsin during the COVID-19 outbreak?
In the face of the COVID-19 outbreak, traveling now comes with some extra challenges. Make a note of these valuable tips before jumping on your flight to Southern Wisconsin:
  • Understand what, if any, restrictions or rules apply to both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book your flight.
  • Wear a face mask during airport screening. A TSA employee will ask you to temporarily lower your mask for ID purposes.
  • Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. After that, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
  • Put any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection.

Which airlines fly to Southern Wisconsin?
Delta offers flights into or near Southern Wisconsin, including 573 that arrive at General Mitchell Intl. Airport (MKE) each month. Figure out your travel dates and then book your fare early for the best deal.
How can I find cheap tickets to Southern Wisconsin?
Book ahead of time, fly to or from nearby airports, avoid school vacation time — there are lots of ways! Another one is to take advantage of Expedia's "flexible dates" function. Search for your Southern Wisconsin flight, then check out the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to Southern Wisconsin was .
How much is a flight to Southern Wisconsin?
One-way flights leaving () sold for as low as in the last seven days. During this period, the cost of a round-trip journey to Southern Wisconsin ranged between and . If you find a fantastic deal, book fast — these prices don't wait around for long.
What are the most popular airports to fly into in Southern Wisconsin?
Get ready to pack your bags and fly into General Mitchell Intl. Airport (MKE), Southern Wisconsin's leading flight hub. Book one of the 2400 flights that touch down at this popular destination each month.
When is the cheapest time to fly to Southern Wisconsin?
Leave for Southern Wisconsin early on in the week and you'll usually be rewarded with cheaper fares. Tuesday is known for being the cheapest day to get on a plane, closely followed by Monday. If you're hoping to avoid the costliest flights, stay away from Saturdays.
How much is a plane ticket to Southern Wisconsin?
In the last seven days, airfares to Southern Wisconsin ranged between and . Prices depend on multiple things, particularly the departure time, airline, seating class and when you make your booking.
Which airlines with flights to Southern Wisconsin employ COVID-19 cleanliness policies?
As lockdowns and restrictions start to lift, airlines are back in the skies with new strategies including physical distancing and an increased supply of face masks, gloves and sanitizer. Here's what some carriers are doing to help stop the spread of COVID-19:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.