Southwest Wisconsin Vacations from ¥93,126

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The Latest Southwest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥93,126
per person
Nov 25 - Nov 29
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
¥193,537
per person
Nov 25 - Nov 29
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to. I know Trump Hotels' bar is high, but this is on another level. Obviously, being a landmark in Chicago, location is the best in Chicago. There is a Langham property right next to it, but this is it. Rooms are well maintained, and the restaurants were excellent. I hope to visit again soon.

Reviewed on Oct 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
¥134,441
per person
Nov 25 - Nov 29
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Cet hôtel est tout simplement parfait. Tout est d'une propreté irréprochable, le buffet du matin compris dans le prix de la chambre est exceptionnel et varie tous les jours, Et que dire de l'emplacement, tout simplement idéal, au coeur de Chicago, au coin de selon moi la plus belle rue de Chicago le Michigan Avenue, à deux pas de la Chicago River. Je vous conseille fortement de faire le tour de bateau Architecture sur la rivière, c'est vraiment intéressant et ça va donnes une vue complètement différente de la ville. Chicago a été un énorme coup de cœur pour moi. Le seul bémol est que si vous y allez en vacances, mois ce fut pour affaire, prévoyez un budget car c'est assez dispendieux.

Reviewed on Oct 12, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥133,892
per person
Nov 25 - Nov 29
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Lovely hotel with a great location. Kind staff. Only slight disappointment is that the fan in our bathroom did not work so it got a bit foggy. But outside of that very small thing this place was perfect.

Reviewed on Oct 11, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥122,640
per person
Nov 25 - Nov 29
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)

Where to stay in Southwest Wisconsin

Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin
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.

A pink water lily in a pond with green lily pads.

Historic Downtown La Crosse

1 out of top 10 points of interest in this area

The abundant dining options and stunning river views are top of the list for many visitors to Historic Downtown La Crosse. A stop by La Crosse Center or Oktoberfest Grounds might round out your trip.

A wooden boardwalk through a forest with moss-covered rock walls.

Lake Delton

1 out of top 10 points of interest in this area

If you're spending some time in Lake Delton, Noah's Ark Waterpark and Mt. Olympus Water and Theme Park are top sights worth seeing.

A calm lake with a city skyline in the background, surrounded by trees.

Monona

Situated on Lake Monona's southeastern shore, this Madison suburb boasts the historic Indian Mounds Park, a site on the National Register of Historic Places.

A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Capitol

While visiting Capitol, you might make a stop by sights like Wisconsin State Capitol and Overture Center for the Arts.

Find the Best Southwest Wisconsin Vacation Packages

Things to do near Southwest Wisconsin

Shopping

For unique gifts, visit the Spring Green General Store, located 32.2km away. The Viking Village Shopping Center, just 30.6km from Southwest Wisconsin, offers a vibrant mix of shopping and entertainment. Don't miss WI River Outings, a charming store 43.5km away for outdoor adventure gear.

Recreation

Explore West Side Park for family-friendly outdoor fun, featuring a playground perfect for relaxation and play. For a serene escape, visit Sauk County Forest, where you can unwind in nature's tranquility. Fireman's Park also offers a peaceful environment for recreation and rejuvenation amidst beautiful landscapes.

Adventure

Explore Miner Hill Trails Park, a scenic hiking trail located 8.0km from Southwest Wisconsin, offering breathtaking views and a sense of adventure. The 400 State Trail, 22.5km away, provides a picturesque journey through nature, while the Meadow Valley Trailhead, 45.1km distant, invites you to discover more stunning landscapes.

Nightlife

In Southwest Wisconsin, enjoy the vibrant nightlife in towns like La Crosse and Platteville, where you'll find lively bars, cozy pubs, and dance clubs. Explore local breweries, live music venues, and seasonal festivals that bring energy to the evenings while connecting with friendly locals.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Southwest Wisconsin

Southwest Wisconsin is an ideal destination for outdoor enthusiasts and those seeking romantic getaways. Visitors can explore urban parks, intriguing caves, and local libraries while enjoying family-friendly activities and cultural experiences. Highlights include the scenic Wisconsin River, picturesque Wisconsin State Parks, and the famous Wisconsin Dells, making it a captivating region for travelers looking to immerse themselves in nature and adventure.

  • Richland County Fairgrounds: Experience the charm of a classic American fair at the Richland County Fairgrounds. Located just 6.4km away, this venue offers family-friendly activities, outdoor entertainment, and a vibrant atmosphere where you can enjoy local crafts, food, and games, making it a perfect spot for creating lasting memories.
  • Pier County Park: A serene natural reserve located 6.4km from Southwest Wisconsin, Pier County Park is ideal for those seeking tranquility. The park features scenic trails for hiking, picnicking areas, and opportunities for wildlife viewing, allowing you to immerse yourself in the beauty of the Wisconsin wilderness.
  • North Park: Situated 8.0km away, North Park is a lively urban park that combines city vibes with outdoor fun. It offers playgrounds, walking paths, and spacious green areas, making it an excellent destination for families to relax and enjoy recreational activities in a vibrant community setting.

Best time to go to Southwest Wisconsin

The best time to visit Southwest Wisconsin can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Southwest Wisconsin falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature around Southwest Wisconsin falls in January, visitor numbers are moderately low and weather is mostly cloudy with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.800000000000001°C)No RainMostly CloudyModerately LowSlightly Low
February20.7°F (-6.300000000000001°C)No RainMostly CloudyModerately LowAverage
March34.7°F (1.5°C)Light RainMostly CloudyAverageSlightly Low
April44.1°F (6.7°C)Light RainMostly CloudyAverageAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June67.8°F (19.9°C)Light RainMostly SunnyModerately HighSlightly High
July71.2°F (21.8°C)Light RainMostly SunnyModerately HighSlightly High
August70.2°F (21.200000000000003°C)Light RainMostly SunnyModerately HighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageAverage
November37.6°F (3.1°C)Light RainMostly SunnyAverageAverage
December23.7°F (-4.6000000000000005°C)Light RainMostly CloudyModerately LowSlightly Low

Tips to save on your trip to Southwest Wisconsin

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Southwest Wisconsin during the low season (March and December to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Southwest 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
¥15,038
¥16,879 total
Oct 23 - Oct 24
includes taxes & fees
7/10 Good! (3,077 reviews)
"Easy access to water park"

Reviewed on Oct 12, 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
¥18,704
¥21,603 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (4,234 reviews)
"Hot tub and pool were great and excellent bed and perfect location."

Reviewed on Oct 11, 2026

The Madison Concourse Hotel and Governor's Club
Natura Vue Resort & Boathouse

Natura Vue Resort & Boathouse

1015 River Rd Wisconsin Dells WI
¥9,260
¥12,168 total
Oct 13 - Oct 14
includes taxes & fees
Natura Vue Resort & Boathouse
See all 3,883 properties in Southwest 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 Southwest Wisconsin attractions

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.
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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.
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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.
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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.
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La Crosse Center

8.8/10 (441 reviews)
Catch an event at La Crosse Center during your trip to La Crosse. Wander the area's riverfront or simply enjoy one of its lively bars.
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Frequently asked questions

How much does a Southwest Wisconsin vacation package cost?
Starting from an incredible ¥93,126, you can handcraft your own Southwest Wisconsin package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Southwest Wisconsin?
If you love scoring a bargain, bundle your bookings into a Southwest Wisconsin vacation package. Whether you're looking for hotels, flights, activities or rental cars, you can browse and book them all in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options globally to pick from. Fly with who you prefer, book a room where you like and save a tidy sum — now that's the ideal escape!
What are the top hotels in Southwest Wisconsin?
Chula Vista Resort, Trademark Collection by Wyndham and Adams Inn know how to make their guests feel at home in Wisconsin Dells. If your travel plans also include Baraboo, check out La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton and Days Inn & Suites by Wyndham Wisconsin Dells. Both are popular with travelers.
How far in advance should I book my Southwest Wisconsin vacation?
It all depends on the airline, but you can usually look up international fares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky travelers occasionally score a cheaper flight just weeks prior to the date of departure.
What does an Expedia Southwest Wisconsin travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Southwest Wisconsin getaway. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Southwest Wisconsin travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything together will make your trip planning easier. So why waste your time or money? Whether you're organizing a luxury city stay with your love or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Southwest Wisconsin Expedia vacation package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and traveling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin vacation package?
Yes, it's possible to cancel your Southwest Wisconsin booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

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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.