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Highland

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Highland Flights as Low as $219

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

Bargain Flight
Tue, Aug 5 - Thu, Aug 14
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Thu, Aug 14, priced at $219 found 3 days ago
Bargain Flight
Thu, Sep 4 - Fri, Sep 5
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$229 Roundtrip, found 4 days ago
$229
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Thu, Sep 4 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Sep 5, priced at $229 found 4 days ago
Delta
Tue, Jul 1 - Wed, Jul 2
MCO
Orlando Intl.
MSN
Dane County Regional
$242 Roundtrip, found 15 hours ago
$242
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Jul 1 from Orlando Intl. to Dane County Regional, returning Wed, Jul 2, priced at $242 found 15 hours ago
Delta
Tue, Aug 19 - Tue, Aug 26
BNA
Nashville Intl.
MSN
Dane County Regional
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 19 from Nashville Intl. to Dane County Regional, returning Tue, Aug 26, priced at $249 found 1 day ago
American Airlines
Tue, Aug 19 - Sat, Aug 23
BNA
Nashville Intl.
MSN
Dane County Regional
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 19 from Nashville Intl. to Dane County Regional, returning Sat, Aug 23, priced at $251 found 1 day ago
Delta
Thu, Jul 10 - Tue, Jul 15
BUF
Buffalo Niagara Intl.
MSN
Dane County Regional
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jul 10 from Buffalo Niagara Intl. to Dane County Regional, returning Tue, Jul 15, priced at $253 found 1 day ago
Delta
Mon, Aug 18 - Tue, Aug 26
BNA
Nashville Intl.
MSN
Dane County Regional
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 18 from Nashville Intl. to Dane County Regional, returning Tue, Aug 26, priced at $253 found 1 day ago
United
Tue, Jul 8 - Tue, Jul 15
BNA
Nashville Intl.
MSN
Dane County Regional
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jul 8 from Nashville Intl. to Dane County Regional, returning Tue, Jul 15, priced at $253 found 3 days ago
Delta
Wed, Jul 9 - Tue, Jul 15
BUF
Buffalo Niagara Intl.
MSN
Dane County Regional
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 9 from Buffalo Niagara Intl. to Dane County Regional, returning Tue, Jul 15, priced at $258 found 1 day ago
United
Tue, Aug 19 - Sat, Aug 23
BNA
Nashville Intl.
MSN
Dane County Regional
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 19 from Nashville Intl. to Dane County Regional, returning Sat, Aug 23, priced at $263 found 1 day ago
Delta
Tue, Jul 8 - Tue, Jul 15
BNA
Nashville Intl.
MSN
Dane County Regional
$264 Roundtrip, found 3 days ago
$264
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jul 8 from Nashville Intl. to Dane County Regional, returning Tue, Jul 15, priced at $264 found 3 days ago
Frontier Airlines
Tue, Jun 24 - Tue, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$271 Roundtrip, found 12 hours ago
$271
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Jun 24 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Tue, Jul 1, priced at $271 found 12 hours ago
Breeze Airways
Wed, Jun 25 - Sat, Jun 28
MCO
Orlando Intl.
MSN
Dane County Regional
$295 Roundtrip, found 15 hours ago
$295
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Jun 25 from Orlando Intl. to Dane County Regional, returning Sat, Jun 28, priced at $295 found 15 hours ago
American Airlines
Tue, Jun 24 - Tue, Jun 24
BOS
Logan Intl.
MSN
Dane County Regional
$335 Roundtrip, found 1 day ago
$335
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 24 from Logan Intl. to Dane County Regional, returning Tue, Jun 24, priced at $335 found 1 day ago
Delta
Thu, Jul 3 - Tue, Jul 29
CSG
Columbus Metropolitan
MSN
Dane County Regional
$395 Roundtrip, found 17 hours ago
$395
Roundtrip
found 17 hours ago
Select Delta flight, departing Thu, Jul 3 from Columbus Metropolitan to Dane County Regional, returning Tue, Jul 29, priced at $395 found 17 hours ago
American Airlines
Tue, Oct 14 - Sun, Oct 19
BNA
Nashville Intl.
LSE
La Crosse Municipal
$477 Roundtrip, found 23 hours ago
$477
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Oct 14 from Nashville Intl. to La Crosse Municipal, returning Sun, Oct 19, priced at $477 found 23 hours ago

Cheap Flights to Highland

Fall in love at first flight with your vacation to Highland 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 Highland on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Highland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highland 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 null airport.

What is the cheapest month to fly to Highland?

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 Highland are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Highland?

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 Highland.

What airport is best to fly into Highland?

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

How much are flights to Highland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $219, 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 Highland?

The trick to saving a stack of cash on your flight to Highland? 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 $219 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$218

Last Minute Hotel Deals in Highland

Don Q Inn
Don Q Inn
2.5 out of 5
3658 State Road 23, Dodgeville, WI
Stay at this hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8/10 Very Good! (1,000 reviews)
"The property is unique and has great antiques, including a WWII plane you can take a look into! The lobby has a great fireplace surrounded by old salon/barber chairs, very cool! Friendly staff and lovely grounds. The room was spacious. The only critique is that the electricity was odd and we could ..."

Reviewed on Jun 14, 2025

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Don Q Inn
Deer Valley Lodge & Golf
Deer Valley Lodge & Golf
2.5 out of 5
401 West Industrial Drive, Barneveld, WI
Book a stay at this golf hotel in Barneveld. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.8/10 Excellent! (601 reviews)
"Thank you for the great stay. We'll definitely visit again."

Reviewed on Jun 15, 2025

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Deer Valley Lodge & Golf
AmericInn by Wyndham Dodgeville
AmericInn by Wyndham Dodgeville
2.5 out of 5
3637 State Road 23, Dodgeville, WI
Book a stay at this business-friendly hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (493 reviews)
"Ok"

Reviewed on Jun 16, 2025

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AmericInn by Wyndham Dodgeville
Holiday Inn Express and Suites-Platteville by IHG
Holiday Inn Express and Suites-Platteville by IHG
2.5 out of 5
55 S ELM ST, Platteville, WI
Book a stay at this business-friendly hotel in Platteville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.6/10 Exceptional! (516 reviews)
"Great place to stay. Easy walk to restaurants. Comfortable bed!"

Reviewed on Jun 18, 2025

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Holiday Inn Express and Suites-Platteville by IHG
The Round Barn Lodge
The Round Barn Lodge
2.5 out of 5
E4830 Us Highway 14, Spring Green, WI
Book a stay at this business-friendly lodge in Spring Green. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
8.4/10 Very Good! (549 reviews)
"Easy to get to, friendly staff, super clean rooms!"

Reviewed on May 27, 2025

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The Round Barn Lodge
AmericInn by Wyndham Boscobel
AmericInn by Wyndham Boscobel
2.5 out of 5
1700 Elm St, Boscobel, WI
Book a stay at this business-friendly hotel in Boscobel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (421 reviews)
"Very nice….attentive crew…."

Reviewed on Jun 16, 2025

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AmericInn by Wyndham Boscobel
Sleep Inn & Suites Lancaster-Platteville
Sleep Inn & Suites Lancaster-Platteville
2.5 out of 5
1600 S Madison Street, Lancaster, WI
Book a stay at this golf hotel in Lancaster. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
9.2/10 Wonderful! (220 reviews)
"Great experience every time . Staff very accommodating. Breakfast is good lots of choices hot choices cold choices yogurts fresh fruit waffles 2 flavors juices milk danish etc. beds are awesome."

Reviewed on May 30, 2025

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Sleep Inn & Suites Lancaster-Platteville
Best Western Dodgeville Inn & Suites
Best Western Dodgeville Inn & Suites
2.5 out of 5
1130 N Johns Street, Dodgeville, WI
Stay at this hotel in Dodgeville. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (595 reviews)
"Outside door to parking lot never opened. We did not ask for a fix. Carpet was wet by exterior door."

Reviewed on Jun 16, 2025

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Best Western Dodgeville Inn & Suites
See all 118 properties in Highland
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.