Southwest Wisconsin Trips (flight + hotel)

Photo by Inbal Arieh

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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
Wisconsin State Capitol building, view from Monona Terrace rooftop.; Shutterstock ID 5305432

Downtown Madison

1 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 Orpheum Theater or Overture Center for the Arts might round out your trip.

Find hotels in Downtown Madison

Things to do near Southwest Wisconsin

Shopping

Discover the Spring Green General Store, a charming spot located 32.2km from Southwest Wisconsin, perfect for unique gifts. The Viking Village Shopping Center, 30.6km away, offers a blend of shopping and entertainment, while WI River Outings, situated 43.5km from the area, provides local treasures and experiences.

Recreation

At West Side Park, enjoy a vibrant playground atmosphere perfect for families, just 9.7km from Southwest Wisconsin. Experience tranquility at Sauk County Forest, renowned for its wellness and relaxation vibes, located 27.4km away. Fireman's Park, a serene recreational area, is also 19.7km away, offering a peaceful retreat.

Adventure

At Miner Hill Trails Park, located 8.0km from Southwest Wisconsin, immerse yourself in breathtaking scenery while hiking through diverse landscapes. The 400 State Trail, 22.5km away, offers a thrilling adventure with picturesque views. For a more tranquil experience, explore Meadow Valley Trailhead, situated 45.1km from the heart of the region.

Nightlife

Southwest Wisconsin's nightlife is vibrant and diverse. Visit the River City Saloon in La Crosse for a lively atmosphere and dance floor. For a more laid-back evening, try The Grumpy Troll in Mount Horeb, known for its craft brews and relaxed pub vibe, perfect for unwinding with friends.

*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 offers a picturesque escape for outdoor enthusiasts and couples alike, featuring attractions such as urban parks, caves, and libraries. Visitors can explore the scenic Wisconsin Dells and the serene Wisconsin River Valley, while also enjoying various state parks. This region caters to families and those seeking a cultural experience, making it a perfect destination for a diverse range of travellers.

  • Richland County Fairgrounds: Experience the lively atmosphere of the Richland County Fairgrounds, a hub for family-friendly events and outdoor activities. With its charming fairground vibe, visitors can enjoy local fairs, exhibits, and various recreational activities that bring the community together, all set against a backdrop of picturesque Wisconsin landscapes.
  • Pier County Park: Explore the natural beauty of Pier County Park, a serene reserve that offers tranquil walking paths and picnic spots. Ideal for nature enthusiasts, this park is perfect for leisurely strolls and birdwatching, allowing you to immerse yourself in the stunning flora and fauna of the area.
  • North Park: Enjoy the vibrant atmosphere at North Park, where urban charm meets outdoor fun. This park features playgrounds, sports facilities, and open spaces for family gatherings, making it a popular spot for both relaxation and recreational activities amidst a city 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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Southwest Wisconsin.
  • 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.

Top hotels in Southwest Wisconsin

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 P6,961 per night from Mar 15 to Mar 16
P6,961
P8,040 total
Mar 15 - Mar 16
includes taxes & fees
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 P2,945 per night from Mar 18 to Mar 19
P2,945
P3,306 total
Mar 18 - Mar 19
includes taxes & fees
7/10 Good! (2,650 reviews)
The pool area was packed on a Saturday evening. Had to wait in line for all the fun slides and the hot tubs. The room was excitingly larger than expected and clean but dated. Each mattress was different and cold air blew in from the heating unit. It is early spring.

Reviewed on Mar 9, 2026

Mt. Olympus Water & Theme Park Resort
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Fully refundableReserve now, pay when you stay
The price is P7,023 per night from Apr 5 to Apr 6
P7,023
P7,883 total
Apr 5 - Apr 6
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
Clean room | Staff | Family-friendly | Pool

Reviewed on Mar 9, 2026

Great Wolf Lodge Wisconsin Dells
See all 3,708 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.

Popular places to visit

Kalahari Indoor Waterpark

Bring the family to Kalahari Indoor Waterpark and have a fun-filled day at this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

Kalahari Indoor Waterpark

Noah's Ark Waterpark

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.

Noah's Ark Waterpark

Frequently asked questions

Can I cancel my flight booking to Southwest Wisconsin due to COVID-19?
Our Customer Service Portal is where you can get important information about changing or canceling your flight due to COVID-19. Before you reserve a seat, it's a good idea to look over the terms and conditions of your preferred carrier too.
What's the best way to find cheap flights to Southwest Wisconsin that have flexible change policies?
It's as easy as counting to three with Expedia. First, enter your preferred travel dates and press "Search." Step 2: Check the "No change fee" box below the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Reserve your flexible and cheap ticket to Southwest Wisconsin.
What are some of the general tips for travelers to Southwest Wisconsin during the COVID-19 outbreak?
With new rules, restrictions and safety measures to follow, travel looks a bit different these days. These are some helpful things to know before you hop on that plane to Southwest Wisconsin:
  • Investigate if any travel restrictions apply to your origin and destination before locking in a flight. Also check if there are any requirements you'll need to follow on arrival, such as taking a COVID-19 test.
  • When you pass through airport screening, do not remove your face mask. You will be asked to lower it briefly for identification purposes. Travelers who refuse to wear a mask may face civil penalties and may also be escorted from the terminal.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. Once that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for scanning.
  • To minimize handling during the screening process, put items such as your belt, phone and wallet into your carry-on instead of into the bins.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA agent will need to touch and open your bag for inspection.

Which airlines fly to Southwest Wisconsin?
Arrange your airfare with United Airlines and then start piecing together your Southwest Wisconsin to-do list. This leading airline provides 238 flights every month to Dane County Regional Airport (MSN), a major gateway.
How can I find cheap tickets to Southwest Wisconsin?
In the last seven days, was the best price for a flight to Southwest Wisconsin. If you want to save even more, book ahead of time and be flexible with your travel dates. Search for your flight to Southwest Wisconsin, then see prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Southwest Wisconsin?
The cost of a round-trip flight to Southwest Wisconsin in the last seven days fluctuated between and . If you were heading one way from (), you could have landed a cheap fare from only .
What are the most popular airports to fly into in Southwest Wisconsin?
Jet into Dane County Regional Airport (MSN) and enjoy all that Southwest Wisconsin has to offer. As the region's main entry point, around 1068 flights touch down here each month.
When is the cheapest time to fly to Southwest Wisconsin?
If you can be flexible with what date you travel to Southwest Wisconsin, try to fly out earlier in the week. The most economical day to take off is usually Tuesday, followed by Monday. Saturday is typically the costliest day, with many vacationers opting to take off on the weekend.
How much is a plane ticket to Southwest Wisconsin?
In the last seven days, fares varied between and . Have a look at our fantastic deals to Southwest Wisconsin, pick your favorite and then start packing your bags.
Which airlines with flights to Southwest Wisconsin employ COVID-19 cleanliness policies?
In response to the current pandemic, many airlines have adopted extra rules and standards to help their passengers fly with peace of mind. Check out what these carriers are doing:
  • 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.
  • United 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.