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Southwest Wisconsin

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Southwest Wisconsin Flights as Low as $259

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Sat, Nov 14 - Mon, Nov 16
BOS
Logan Intl.
MSN
Dane County Regional
$259 Roundtrip, found 4 days ago
$259
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Sat, Nov 14 from Logan Intl. to Dane County Regional, returning Mon, Nov 16, priced at $259 found 4 days ago
Bargain Flight
Tue, Sep 1 - Sat, Sep 5
BOS
Logan Intl.
MSN
Dane County Regional
$270 Roundtrip, found 4 days ago
$270
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Sep 1 from Logan Intl. to Dane County Regional, returning Sat, Sep 5, priced at $270 found 4 days ago
Delta
Sat, Sep 19 - Tue, Oct 6
BOS
Logan Intl.
MSN
Dane County Regional
$313 Roundtrip, found 18 hours ago
$313
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Sep 19 from Logan Intl. to Dane County Regional, returning Tue, Oct 6, priced at $313 found 18 hours ago
Delta
Tue, Sep 8 - Tue, Sep 29
BOS
Logan Intl.
MSN
Dane County Regional
$320 Roundtrip, found 18 hours ago
$320
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Sep 8 from Logan Intl. to Dane County Regional, returning Tue, Sep 29, priced at $320 found 18 hours ago
Delta
Sat, Sep 19 - Wed, Oct 7
BOS
Logan Intl.
MSN
Dane County Regional
$323 Roundtrip, found 18 hours ago
$323
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Sep 19 from Logan Intl. to Dane County Regional, returning Wed, Oct 7, priced at $323 found 18 hours ago
American Airlines
Tue, Sep 1 - Sat, Sep 5
BOS
Logan Intl.
MSN
Dane County Regional
$331 Roundtrip, found 4 days ago
$331
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 1 from Logan Intl. to Dane County Regional, returning Sat, Sep 5, priced at $331 found 4 days ago
United
Tue, Sep 1 - Sat, Sep 5
BOS
Logan Intl.
MSN
Dane County Regional
$341 Roundtrip, found 4 days ago
$341
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 1 from Logan Intl. to Dane County Regional, returning Sat, Sep 5, priced at $341 found 4 days ago
United
Tue, Sep 1 - Sat, Sep 5
BOS
Logan Intl.
MSN
Dane County Regional
$346 Roundtrip, found 4 days ago
$346
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 1 from Logan Intl. to Dane County Regional, returning Sat, Sep 5, priced at $346 found 4 days ago
Delta
Thu, Sep 24 - Tue, Sep 29
BOS
Logan Intl.
MSN
Dane County Regional
$347 Roundtrip, found 18 hours ago
$347
Roundtrip
found 18 hours ago
Select Delta flight, departing Thu, Sep 24 from Logan Intl. to Dane County Regional, returning Tue, Sep 29, priced at $347 found 18 hours ago
Delta
Thu, Sep 10 - Tue, Sep 29
BOS
Logan Intl.
MSN
Dane County Regional
$355 Roundtrip, found 18 hours ago
$355
Roundtrip
found 18 hours ago
Select Delta flight, departing Thu, Sep 10 from Logan Intl. to Dane County Regional, returning Tue, Sep 29, priced at $355 found 18 hours ago
Delta
Thu, Sep 17 - Tue, Oct 6
BOS
Logan Intl.
MSN
Dane County Regional
$357 Roundtrip, found 18 hours ago
$357
Roundtrip
found 18 hours ago
Select Delta flight, departing Thu, Sep 17 from Logan Intl. to Dane County Regional, returning Tue, Oct 6, priced at $357 found 18 hours ago
United
Tue, Sep 1 - Sat, Sep 5
BOS
Logan Intl.
MSN
Dane County Regional
$359 Roundtrip, found 4 days ago
$359
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 1 from Logan Intl. to Dane County Regional, returning Sat, Sep 5, priced at $359 found 4 days ago
United
Tue, Sep 1 - Sat, Sep 5
BOS
Logan Intl.
MSN
Dane County Regional
$361 Roundtrip, found 4 days ago
$361
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 1 from Logan Intl. to Dane County Regional, returning Sat, Sep 5, priced at $361 found 4 days ago
Delta
Thu, Sep 10 - Sat, Sep 26
BOS
Logan Intl.
MSN
Dane County Regional
$365 Roundtrip, found 18 hours ago
$365
Roundtrip
found 18 hours ago
Select Delta flight, departing Thu, Sep 10 from Logan Intl. to Dane County Regional, returning Sat, Sep 26, priced at $365 found 18 hours ago
Delta
Thu, Sep 17 - Wed, Oct 7
BOS
Logan Intl.
MSN
Dane County Regional
$367 Roundtrip, found 18 hours ago
$367
Roundtrip
found 18 hours ago
Select Delta flight, departing Thu, Sep 17 from Logan Intl. to Dane County Regional, returning Wed, Oct 7, priced at $367 found 18 hours ago
Delta
Wed, Jul 15 - Tue, Jul 21
DAB
Daytona Beach Intl.
MSN
Dane County Regional
$407 Roundtrip, found 15 hours ago
$407
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Jul 15 from Daytona Beach Intl. to Dane County Regional, returning Tue, Jul 21, priced at $407 found 15 hours ago

Cheap Flights to Southwest Wisconsin

Fall in love at first flight with your vacation to Southwest Wisconsin by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Southwest Wisconsin on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Southwest Wisconsin, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Southwest Wisconsin

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Southwest Wisconsin with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the RFD airport.

What is the cheapest month to fly to Southwest Wisconsin?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Southwest Wisconsin are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Southwest Wisconsin?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Southwest Wisconsin.

What airport is best to fly into Southwest Wisconsin?

When you’re planning your trip to Southwest Wisconsin, convenience is the name of the game. Luckily, Southwest Wisconsin Dane County Regional Airport is nearby so you can deplane and get going on checking off everything on your Southwest Wisconsin must-do list.

How much are flights to Southwest Wisconsin?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Southwest Wisconsin on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $259, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Southwest Wisconsin?

The trick to saving a stack of cash on your flight to Southwest Wisconsin? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $259 right now, why wait?

Southwest Wisconsin Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$168

Last Minute Hotel Deals in Southwest Wisconsin

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road Wisconsin Dells WI
Book a stay at this family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access, and parking (surcharge). Our guests praise the ...
7/10 Good! (2,863 reviews)
"The room itself was decent, but there were a few cleanliness and maintenance issues that could be improved. The bed sheets didn’t appear to be completely clean, as there were visible stains. The refrigerator was clean, which was appreciated. However, the floors could have used a thorough mopping. ..."

Reviewed on Jul 13, 2026

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Mt. Olympus Water & Theme Park Resort
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
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (3,999 reviews)
"Great stay! The room was clean, comfortable, and quiet. The hotel was in a fantastic location, making it easy to walk to restaurants and explore downtown Madison. The staff was friendly and helpful, and everything was well maintained. We’d definitely stay here again!"

Reviewed on Jul 12, 2026

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The Madison Concourse Hotel and Governor's Club
Dellshire Resort

Dellshire Resort

3.5 out of 5
2277 Wisconsin Dells Pkwy Wisconsin Dells WI
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Mt. Olympus Water and Theme ...
9/10 Wonderful! (153 reviews)
"The property was beautiful, rooms were big, and amenities were great."

Reviewed on Jul 12, 2026

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Dellshire Resort
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
8/10 Very Good! (1,365 reviews)
"Breakfast was subpar — several options, but looked very unappetizing. The room was a disaster. We walked in and it stunk of mildew & cat urine. It was awful! The sheets had stains, towels had stains, hair in the shower, and pubic hair on the toilet tank. Just disgusted. We were doing to ask for a ..."

Reviewed on Jul 12, 2026

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Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,020 reviews)
"Very nice and clean"

Reviewed on Jul 11, 2026

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Best Western Plus InnTowner Madison
Natura Treescape Resort

Natura Treescape Resort

2.5 out of 5
400 County Road A Wisconsin Dells WI
Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, 2 indoor pools, and a private beach. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (1,145 reviews)
"We booked a tree house and we got a tiny house instead. The ad said the inflatable lake was close, but was 10 miles away. Lot of false information."

Reviewed on Jul 12, 2026

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Natura Treescape Resort
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Book a stay at this family-friendly resort in Baraboo. Enjoy free WiFi, 6 indoor pools, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (1,027 reviews)
"The only negative is they do charge $21.00 per car for parking. It’s overpriced on top of the room prices. Room prices have reached the limits for normal blue collar workers. I believe SOON it will take its toll on the massive water park resorts. The Dells in general is now out priced. You can fly ..."

Reviewed on Jul 12, 2026

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Great Wolf Lodge Wisconsin Dells
Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

2.5 out of 5
2504 Wisconsin Dells Parkway Wisconsin Dells WI
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,817 reviews)
"The best thing is the swimming pools"

Reviewed on Jul 12, 2026

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Days Inn & Suites by Wyndham Wisconsin Dells
See all 3,833 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.

Top Hotels With Free Airport Shuttle

Best Western East Towne Suites

Best Western East Towne Suites

2.5 out of 5
4801 Annamark Dr Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (1,013 reviews)
"Not clean, smelt bad, stained mattresses, dirty"

Reviewed on Jul 11, 2026

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Best Western East Towne Suites
AmericInn by Wyndham La Crosse Riverfront-Conference Center

AmericInn by Wyndham La Crosse Riverfront-Conference Center

3 out of 5
1835 Rose Street La Crosse WI
Book a stay at this beach hotel in La Crosse. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
7.6/10 Good! (1,004 reviews)
"They are in the midst of remodeling, so one would hope some of the issues would resolve with completion of that project. Our original handicap room had a leaking showerhead and a wet bathroom floor upon our arrival. Once the maintenance person stopped the drip, there was no water to the shower at ..."

Reviewed on Jul 11, 2026

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AmericInn by Wyndham La Crosse Riverfront-Conference Center
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
8/10 Very Good! (1,365 reviews)
"Breakfast was subpar — several options, but looked very unappetizing. The room was a disaster. We walked in and it stunk of mildew & cat urine. It was awful! The sheets had stains, towels had stains, hair in the shower, and pubic hair on the toilet tank. Just disgusted. We were doing to ask for a ..."

Reviewed on Jul 12, 2026

Get rates
Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,020 reviews)
"Very nice and clean"

Reviewed on Jul 11, 2026

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Best Western Plus InnTowner Madison
Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
22 S Carroll Street Madison WI
Book a stay at this spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,014 reviews)
"Great location"

Reviewed on Jul 12, 2026

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Best Western Premier Park Hotel
AmericInn by Wyndham Prairie du Chien

AmericInn by Wyndham Prairie du Chien

3 out of 5
37502 Us Highway 35 And 18 S Prairie Du Chien WI
Book a stay at this business-friendly hotel in Prairie Du Chien. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (635 reviews)
"Clean, friendly, and great parking"

Reviewed on Jul 10, 2026

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AmericInn by Wyndham Prairie du Chien
See all 3,833 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.