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Highland

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Highland Flights as Low as $213

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
$213 Roundtrip, found 14 hours ago
$213
Roundtrip
found 14 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 $213 found 14 hours ago
American Airlines
Mon, Jul 20 - Wed, Aug 5
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Jul 20 from O'Hare Intl. to La Crosse Municipal, returning Wed, Aug 5, priced at $229 found 2 hours ago
Bargain Flight
Tue, Apr 14 - Mon, Apr 20
DTW
Detroit Metropolitan Wayne County
MSN
Dane County Regional
$230 Roundtrip, found 11 hours ago
$230
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Tue, Apr 14 from Detroit Metropolitan Wayne County to Dane County Regional, returning Mon, Apr 20, priced at $230 found 11 hours ago
American Airlines
Mon, Jul 20 - Sat, Aug 1
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$244 Roundtrip, found 20 hours ago
$244
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Mon, Jul 20 from O'Hare Intl. to La Crosse Municipal, returning Sat, Aug 1, priced at $244 found 20 hours ago
American Airlines
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$250 Roundtrip, found 5 hours ago
$250
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $250 found 5 hours ago
American Airlines
Mon, Jul 20 - Fri, Jul 31
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jul 20 from O'Hare Intl. to La Crosse Municipal, returning Fri, Jul 31, priced at $259 found 1 day ago
American Airlines
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$259 Roundtrip, found 5 hours ago
$259
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $259 found 5 hours ago
American Airlines
Mon, Jul 20 - Sun, Aug 2
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jul 20 from O'Hare Intl. to La Crosse Municipal, returning Sun, Aug 2, priced at $264 found 1 day ago
American Airlines
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$269 Roundtrip, found 5 hours ago
$269
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $269 found 5 hours ago
American Airlines
Thu, Jul 16 - Sat, Aug 1
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 16 from O'Hare Intl. to La Crosse Municipal, returning Sat, Aug 1, priced at $274 found 1 day ago
American Airlines
Thu, Apr 9 - Sat, Apr 11
ORD
O'Hare Intl.
MSN
Dane County Regional
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Apr 9 from O'Hare Intl. to Dane County Regional, returning Sat, Apr 11, priced at $275 found 2 days ago
American Airlines
Wed, Apr 8 - Sat, Apr 25
DTW
Detroit Metropolitan Wayne County
LSE
La Crosse Municipal
$311 Roundtrip, found 5 days ago
$311
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 $311 found 5 days ago
American Airlines
Mon, Jun 29 - Sat, Jul 4
BUF
Buffalo Niagara Intl.
MSN
Dane County Regional
$320 Roundtrip, found 5 hours ago
$320
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Jun 29 from Buffalo Niagara Intl. to Dane County Regional, returning Sat, Jul 4, priced at $320 found 5 hours ago
Delta
Tue, Apr 14 - Mon, Apr 20
DTW
Detroit Metropolitan Wayne County
MSN
Dane County Regional
$396 Roundtrip, found 11 hours ago
$396
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Apr 14 from Detroit Metropolitan Wayne County to Dane County Regional, returning Mon, Apr 20, priced at $396 found 11 hours ago
American Airlines
Sat, Apr 4 - Tue, Apr 21
BUF
Buffalo Niagara Intl.
LSE
La Crosse Municipal
$549 Roundtrip, found 1 day ago
$549
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 4 from Buffalo Niagara Intl. to La Crosse Municipal, returning Tue, Apr 21, priced at $549 found 1 day ago
American Airlines
Fri, Apr 10 - Sat, Apr 18
YYZ
Pearson Intl.
LSE
La Crosse Municipal
$617 Roundtrip, found 3 days ago
$617
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Apr 10 from Pearson Intl. to La Crosse Municipal, returning Sat, Apr 18, priced at $617 found 3 days 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 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 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 $213, 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 $213 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$212

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! (1,001 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! (295 reviews)
Great town!

Reviewed on Mar 21, 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
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! (667 reviews)
Gym looked ok, hottub we never used, waste of money cause we never had time, we didnt like you couldnt use after 11pm even in a private room that wasnt cheap

Reviewed on Mar 22, 2026

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Ramada by Wyndham Richland Center
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! (580 reviews)
Convenient location and friendly staff! Recommended!

Reviewed on Mar 22, 2026

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Holiday Inn Express and Suites-Platteville by IHG
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! (689 reviews)
Booked a double queen but they were not Queen beds, they were full size. Lamp shade needed dusting, pool corners were gray. Quiet time not inforced and kind allowed to run through the halls. Parents were drinking in the pool while other kids were swimming and not advised to leave the pool area.

Reviewed on Mar 22, 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! (483 reviews)
No pets so no concern other than the non service dog who shared the facility in the dining area. Not the most sanitary of conditions.

Reviewed on Mar 23, 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 123 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.