Southwest Wisconsin Vacations from ₩544,118

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The Latest Southwest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Price was ₩657,820, price is now ₩544,118 per person
₩544,118
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.8/10 Excellent! (1,555 reviews)
Clean room nice staff

Reviewed on Jan 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₩841,634, price is now ₩578,395 per person
₩578,395
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!

Reviewed on Jan 11, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ₩827,394, price is now ₩658,103 per person
₩658,103
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights

Reviewed on Jan 8, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩738,239, price is now ₩595,602 per person
₩595,602
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
Hospitality over all was top tier! Will definitely stay again

Reviewed on Jan 11, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ₩733,186, price is now ₩593,931 per person
₩593,931
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Clean room, amazinggggg views, everyone was so nice. Must go downstairs to Toro and get a martini from John!!

Reviewed on Jan 10, 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
Madison showing a garden, a house and flowers

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

Find the Best Southwest Wisconsin Vacation Packages

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 ₩195,666 per night from Jan 29 to Jan 30
₩195,666
₩225,993 total
Jan 29 - Jan 30
includes taxes & fees
9.4/10 Exceptional! (3,437 reviews)
Amazing property. Will be back n

Reviewed on Jan 11, 2026

The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is ₩154,345 per night from Jan 13 to Jan 14
₩154,345
₩178,269 total
Jan 13 - Jan 14
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Great amenities and really friendly staff.

Reviewed on Jan 9, 2026

DoubleTree by Hilton Madison East
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is ₩106,486 per night from Jan 19 to Jan 20
₩106,486
₩122,990 total
Jan 19 - Jan 20
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
The front dest staff were exceptional, always a smiling face and a welcoming greeting. The room was clean and comfortable. I am confused about the billing. I was charged, but also credited for more than the charge of the room.

Reviewed on Jan 3, 2026

Hampton Inn & Suites Madison-West
See all 3,681 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.

Discover the most popular places to visit in Southwest Wisconsin

Christmas Mountain

Hit the slopes at Christmas Mountain during your trip to Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

Christmas Mountain

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

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.