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Highland

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Highland Flights as Low as $215

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

Bargain Flight
Tue, Jun 16 - Sat, Jun 20
DTW
Detroit Metropolitan Wayne County
MSN
Dane County Regional
$215 Roundtrip, found 5 hours ago
$215
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Jun 16 from Detroit Metropolitan Wayne County to Dane County Regional, returning Sat, Jun 20, priced at $215 found 5 hours ago
Bargain Flight
Tue, Apr 7 - Mon, Apr 13
DTW
Detroit Metropolitan Wayne County
MSN
Dane County Regional
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Apr 7 from Detroit Metropolitan Wayne County to Dane County Regional, returning Mon, Apr 13, priced at $230 found 2 days ago
Bargain Flight
Tue, Apr 14 - Mon, Apr 20
DTW
Detroit Metropolitan Wayne County
MSN
Dane County Regional
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Apr 14 from Detroit Metropolitan Wayne County to Dane County Regional, returning Mon, Apr 20, priced at $242 found 1 day ago
American Airlines
Wed, Apr 8 - Sat, Apr 25
DTW
Detroit Metropolitan Wayne County
LSE
La Crosse Municipal
$264 Roundtrip, found 5 days ago
$264
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 8 from Detroit Metropolitan Wayne County to La Crosse Municipal, returning Sat, Apr 25, priced at $264 found 5 days ago
American Airlines
Sun, Apr 5 - Thu, Apr 16
DTW
Detroit Metropolitan Wayne County
LSE
La Crosse Municipal
$267 Roundtrip, found 5 days ago
$267
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Apr 5 from Detroit Metropolitan Wayne County to La Crosse Municipal, returning Thu, Apr 16, priced at $267 found 5 days ago
American Airlines
Sat, Apr 11 - Sat, Apr 25
BNA
Nashville Intl.
LSE
La Crosse Municipal
$284 Roundtrip, found 5 days ago
$284
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 11 from Nashville Intl. to La Crosse Municipal, returning Sat, Apr 25, priced at $284 found 5 days ago
American Airlines
Fri, Apr 17 - Sat, May 2
BNA
Nashville Intl.
LSE
La Crosse Municipal
$285 Roundtrip, found 5 days ago
$285
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Apr 17 from Nashville Intl. to La Crosse Municipal, returning Sat, May 2, priced at $285 found 5 days ago
American Airlines
Tue, Apr 14 - Mon, May 4
BNA
Nashville Intl.
LSE
La Crosse Municipal
$288 Roundtrip, found 5 days ago
$288
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Apr 14 from Nashville Intl. to La Crosse Municipal, returning Mon, May 4, priced at $288 found 5 days ago
American Airlines
Wed, May 27 - Wed, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
LSE
La Crosse Municipal
$298 Roundtrip, found 3 days ago
$298
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to La Crosse Municipal, returning Wed, Jun 10, priced at $298 found 3 days ago
Bargain Flight
Tue, May 19 - Tue, May 26
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, May 19 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Tue, May 26, priced at $340 found 1 day ago
Delta
Tue, Apr 14 - Mon, Apr 20
DTW
Detroit Metropolitan Wayne County
MSN
Dane County Regional
$385 Roundtrip, found 1 day ago
$385
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Apr 14 from Detroit Metropolitan Wayne County to Dane County Regional, returning Mon, Apr 20, priced at $385 found 1 day ago
Frontier Airlines
Sun, Apr 12 - Thu, Apr 16
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$423 Roundtrip, found 1 day ago
$423
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 12 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Thu, Apr 16, priced at $423 found 1 day ago
American Airlines
Thu, Apr 30 - Sun, May 3
RDU
Raleigh - Durham Intl.
LSE
La Crosse Municipal
$524 Roundtrip, found 1 hour ago
$524
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Apr 30 from Raleigh - Durham Intl. to La Crosse Municipal, returning Sun, May 3, priced at $524 found 1 hour ago
American Airlines
Wed, Apr 22 - Sat, May 9
ART
Watertown Intl.
LSE
La Crosse Municipal
$576 Roundtrip, found 6 days ago
$576
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Apr 22 from Watertown Intl. to La Crosse Municipal, returning Sat, May 9, priced at $576 found 6 days ago
Swiss International Air Lines
Mon, May 18 - Mon, Jun 1
FRA
Frankfurt Intl.
LSE
La Crosse Municipal
$914 Roundtrip, just found
$914
Roundtrip
just found
Select Swiss International Air Lines flight, departing Mon, May 18 from Frankfurt Intl. to La Crosse Municipal, returning Mon, Jun 1, priced at $914 just found
British Airways
Mon, May 18 - Mon, Jun 1
FRA
Frankfurt Intl.
LSE
La Crosse Municipal
$959 Roundtrip, just found
$959
Roundtrip
just found
Select British Airways flight, departing Mon, May 18 from Frankfurt Intl. to La Crosse Municipal, returning Mon, Jun 1, priced at $959 just found

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 June, 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 12 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 $215, 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 $215 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$215

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 ...
8.2/10 Very Good! (1,001 reviews)
Clearly there has never been a fire inspection done for this facility. Everything is ran by extension cords. Exposed wires and outlets held by duct tape. Luke warm water at best in the tub. Upon check in I showed my receipt where I booked 2 rooms and paid a deposit of half the room total for each ...

Reviewed on Mar 15, 2026

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Don Q Inn
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 ...
9.4/10 Exceptional! (293 reviews)
Very friendly staff. Love pet friendly hotels.

Reviewed on Mar 13, 2026

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Sleep Inn & Suites Lancaster-Platteville
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 ...
8.4/10 Very Good! (579 reviews)
Everything was wonderful! Room was spotless, bed was comfortable. The temperature of the hot tub was perfect and very relaxing! Perfect for the long drive aches! Kim at the front desk was the amazing host with valuable knowledge for places to visit and gave special attention to our dog. Thanks, ...

Reviewed on Mar 15, 2026

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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 ...
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Holiday Inn Express and Suites-Platteville by IHG
Ramada by Wyndham Richland Center

Ramada by Wyndham Richland Center

3 out of 5
1450 Veterans Dr Richland Center WI
Book a stay at this business-friendly hotel in Richland Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
8.4/10 Very Good! (665 reviews)
Parking was good. Close to the Phoenix center

Reviewed on Mar 9, 2026

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Ramada by Wyndham Richland Center
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! (688 reviews)
Overall okay stay. Large stain on comforter. Food on the remote. Few options for breakfast. Otherwise everything else is "okay"

Reviewed on Mar 1, 2026

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Deer Valley Lodge & Golf
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! (481 reviews)
Very clean hotel. Clean pool. The bed was very firm and the fan in the bathroom was extremely loud. Staff was very friendly. Nice breakfast options

Reviewed on Feb 28, 2026

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AmericInn by Wyndham Boscobel
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! (648 reviews)
Clean room, good price, very happy with stay. Second time user.

Reviewed on Mar 8, 2026

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Best Western Dodgeville Inn & Suites
See all 124 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.