Southern Wisconsin Vacations from ￥264,532

Book a Hotel + Flight or Car together to unlock savings

Photo by Evae

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Southern Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥264,532
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Great service

Reviewed on Oct 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥434,344
per person
Nov 28 - Dec 3
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The room was beautiful and clean. I have no complaints regarding the room or staff. I did go to the rooftop bar and wish they had seats at the bar. Kind of defeated the purpose of going to a bar solo and the only available seats are at tables or near the edge of the balcony. Other than that service was a bit slow at the rooftop bar. However, the staff at check-in/check out were so helpful and attentive. I enjoyed the Halloween decorations. I will definitely be back in the future.

Reviewed on Oct 13, 2026

The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
￥293,826
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Milwaukee (MKE)
9.6/10 Exceptional! (2,283 reviews)
Kind staff and gorgeous interiors. Truly a classic hotel.

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
￥408,276
per person
Nov 28 - Dec 3
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
￥270,010
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,187 reviews)
The room was clean, comfortable and safe. The staff were incredibly informative. The lication was THE BEST.

Reviewed on Oct 13, 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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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
A large domed building surrounded by modern cityscape and a body of water.

Downtown Madison

2 out of top 10 points of interest in this area

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Overture Center for the Arts or Orpheum Theater might round out your trip.

Find hotels in Downtown Madison
A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

Find hotels in West Allis
A waterfront cityscape at dusk with a calm river reflecting buildings and a bridge.

Wauwatosa

Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town.

Find hotels in Wauwatosa
A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

Find hotels in Historic Third Ward

Find the Best Southern Wisconsin Vacation Packages

Southern Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
￥15,673
￥17,595 total
Oct 15 - Oct 16
includes taxes & fees
7/10 Good! (3,085 reviews)
"Great large room. The kids loved the bunk beds. There is no staff at the property check in etc is in a completely different building a mile or so away. Not coffee etc at the hotel Or in the room. But we really enjoyed the stay and the kids loved the water park (again you have to drive there i didn’t ..."

Reviewed on Oct 13, 2026

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

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI
￥18,743
￥21,649 total
Nov 1 - Nov 2
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
￥14,723
￥17,358 total
Nov 10 - Nov 11
includes taxes & fees
8.6/10 Excellent! (1,534 reviews)
"We picked this hotel because of the connecting bridge to the conference center. Unfortunately it was only open 1 of the days we were there. We were vendors at a conference and had to transport all of our booth items on the street level rather than getting to use the direct bridge. The hotel staff ..."

Reviewed on Oct 12, 2026

Hyatt Regency Milwaukee
See all 7,676 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.

Stay near popular Southern Wisconsin attractions

A sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.
Photo by trenton.badillo

American Family Field

9.0/10 (2,832 reviews)
Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
See properties
A cityscape with a variety of buildings, including a prominent white structure with a curved roof, a tall tower, and a mix of older and modern architecture.

Fiserv Forum

9.2/10 (2,312 reviews)
Catch an event at Fiserv Forum during your trip to Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties
A water park with a large Ferris wheel and a water slide.

Mt. Olympus Water and Theme Park

7.4/10 (1,284 reviews)
Bring the kids to Mt. Olympus Water and Theme Park and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.
See properties
A stone archway with inscriptions and statues, surrounded by greenery.

Camp Randall Stadium

9.0/10 (1,067 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.
See properties

Kalahari Indoor Waterpark

8.8/10 (445 reviews)
Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.
See properties

Noah's Ark Waterpark

8.4/10 (959 reviews)
Bring your family to Noah's Ark Waterpark and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
See properties

Chula Vista Waterparks

7.6/10 (630 reviews)
Enjoy a stop at Chula Vista Waterparks, an entertaining place to visit in Wisconsin Dells. While you're in the area, stroll along the riverfront.
See properties

Alliant Energy Center

8.6/10 (944 reviews)
Catch an event at Alliant Energy Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Frequently asked questions

How much does a Southern Wisconsin vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Southern Wisconsin from just ￥264,532. And the more you bundle, the more you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Southern Wisconsin?
Our Southern Wisconsin vacation packages promise plenty of savings for the savvy traveler. For the best deal, simply bundle your flights, hotels and activities into one neat package. But great bargains are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels throughout the world to choose from. Whatever your style, there's a vacation package with your name on it.
Where should I stay in Southern Wisconsin?
To see popular sights like Milwaukee Art Museum and American Family Field, Milwaukee is the place to be. Lots of travelers also love visiting Appleton, home to Gardens of the Fox Cities and Hearthstone Historic House Museum. If time is on your side, why not visit both cities?
What are the top hotels in Southern Wisconsin?
When it comes to hotels in Milwaukee, Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr are among the favorites. If you're also staying in Wisconsin Dells, Inn of the Pines and Silver Spruce Resort are waiting to welcome you.
How far in advance should I book my Southern Wisconsin vacation?
Savvy travelers often book early. You can usually start comparing international fares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Cheap prices sometimes occur just weeks before departure.
What does an Expedia Southern Wisconsin travel package include?
From hotels and flights to car rentals, Expedia can help you put together a Southern Wisconsin package that works for you. Heading away for a few weeks? Check out a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, a flight and hotel deal could be more your style. Tours and activities can be added once you've made your booking. Our packages make it simple to save and plan.
What should I know before booking a Southern Wisconsin travel package?
So many places to travel to, so many things to do. With a travel package, you can cross more of them off your list. Combine your flights, rental cars and hotels and see how much you save.
If I'm not able to travel, can I cancel my Southern Wisconsin vacation package?
Yes, you can cancel your Southern Wisconsin booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Explore a world of travel with Expedia