Southwest Wisconsin Vacation Packages

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Your Southwest Wisconsin Vacation

Choose a vacation package to Southwest Wisconsin and make planning your adventure a breeze. With all the details arranged before you leave, you can focus on enjoying every second in this destination. A trip to Southwest Wisconsin wouldn't be complete without experiencing some of its best cities, starting with Wisconsin Dells. A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. La Crosse is another favourite city with Southwest Wisconsin travellers. Visitors to this destination enjoy Oktoberfest Grounds and Onalaska Omni Centre. From the moment you book your Southwest Wisconsin vacation to when you get back home, Expedia will take care of you every step of the way.

Top Southwest Wisconsin Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield

4 out of 5
Price was CA $916, price is now CA $670 per person
CA $670
per person
Jun 18 - Jun 22
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
I booked this property after a day at O'Hare airport and multiple flight cancellations. I was greeted and checked in efficiently, had a drink and dinner and retired to a very comfortable and clean room. Breakfast the next day consusted of an excellent omelet. Overall a very comfortable and well appointed hotel. Thank you!

Reviewed on Mar 16, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,931, price is now CA $1,301 per person
CA $1,301
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.

Reviewed on Apr 11, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,118, price is now CA $768 per person
CA $768
per person
Jun 29 - Jul 3
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!

Reviewed on Apr 3, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,411 per person
CA $1,411
per person
Jun 16 - Jun 19
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The room was clean, spacious, with good views.

Reviewed on Apr 12, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,075, price is now CA $1,522 per person
CA $1,522
per person
Jun 18 - Jun 21
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
I booked this stay specifically because I saw they had a steam room and Sauna. They were both very pleasant and available 24/7. The room was very high quality with great views but if the city. The game rooms looked really nice and spacious but I sadly didn’t have time to enjoy that aspect of the hotel. There is also a great cafe and bakery connected to the lobby. I’m excited to book here again with a little more time to make the most of my stay

Reviewed on Apr 11, 2026

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

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

Ready to book your vacation to Southwest Wisconsin?

 

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Southwest 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 CA $173 per night from Apr 19 to Apr 20
CA $173
CA $200 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (3,638 reviews)
Clean room, friendly staff, was there for a conference so the ballrooms were clean and functional.

Reviewed on Apr 12, 2026

The Madison Concourse Hotel and Governor's Club
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 CA $165 per night from Apr 13 to Apr 14
CA $165
CA $185 total
Apr 13 - Apr 14
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
I loved the stay, they offer everything that they have with the room, they was very clean, and the staff was friendly and helpful. I will definitely be back.

Reviewed on Apr 8, 2026

Great Wolf Lodge Wisconsin Dells
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 CA $69 per night from Apr 14 to Apr 15
CA $69
CA $78 total
Apr 14 - Apr 15
includes taxes & fees
7/10 Good! (2,703 reviews)
I never do reviews I rarely have bad things to say but I have never had such terrible stay somewhere ,First the check in area is across town from the actual resort wouldve been nice to know before booking , 2nd we get there get up to the room with all of our luggage and the room is filthy and I mean ...

Reviewed on Apr 12, 2026

Mt. Olympus Water & Theme Park Resort
See all 3,743 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.
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Discover the most popular places to visit in Southwest Wisconsin

Slidewheel water at a water park.

Mt. Olympus Water and Theme Park

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.

Mt. Olympus Water and Theme Park
Casino hotel and convention center by Upper Mississippi on calm misty morning at Dubuque Iowa

Q Casino

Why not roll the dice with a visit to Q Casino during your visit to Dubuque? Make time to visit the area's casinos, or simply enjoy its top-notch restaurants.

Q Casino

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 lakeside or experience the entertainment choices in this family-friendly area.

Kalahari Indoor 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.