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Highland

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Highland Flights as Low as $217

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

Delta
Tue, Apr 15 - Tue, Apr 22
MCO
Orlando Intl.
MSN
Dane County Regional
$217 Roundtrip, found 23 hours ago
$217
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Apr 15 from Orlando Intl. to Dane County Regional, returning Tue, Apr 22, priced at $217 found 23 hours ago
Delta
Sat, Aug 9 - Wed, Aug 13
IND
Indianapolis Intl.
MSN
Dane County Regional
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 9 from Indianapolis Intl. to Dane County Regional, returning Wed, Aug 13, priced at $219 found 1 day ago
Delta
Wed, Mar 5 - Tue, Mar 11
PDX
Portland Intl.
MSN
Dane County Regional
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Mar 5 from Portland Intl. to Dane County Regional, returning Tue, Mar 11, priced at $232 found 4 days ago
United
Wed, Mar 5 - Tue, Mar 11
PDX
Portland Intl.
MSN
Dane County Regional
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select United flight, departing Wed, Mar 5 from Portland Intl. to Dane County Regional, returning Tue, Mar 11, priced at $234 found 4 days ago
United
Wed, Mar 5 - Tue, Mar 11
PDX
Portland Intl.
MSN
Dane County Regional
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select United flight, departing Wed, Mar 5 from Portland Intl. to Dane County Regional, returning Tue, Mar 11, priced at $237 found 4 days ago
Delta
Wed, Jun 18 - Wed, Jun 25
AUS
Austin-Bergstrom Intl.
MSN
Dane County Regional
$259 Roundtrip, found 17 hours ago
$259
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Jun 18 from Austin-Bergstrom Intl. to Dane County Regional, returning Wed, Jun 25, priced at $259 found 17 hours ago
United
Wed, Mar 5 - Tue, Mar 11
PDX
Portland Intl.
MSN
Dane County Regional
$264 Roundtrip, found 4 days ago
$264
Roundtrip
found 4 days ago
Select United flight, departing Wed, Mar 5 from Portland Intl. to Dane County Regional, returning Tue, Mar 11, priced at $264 found 4 days ago
Delta
Tue, Mar 11 - Wed, Mar 26
TUL
Tulsa Intl.
MSN
Dane County Regional
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 11 from Tulsa Intl. to Dane County Regional, returning Wed, Mar 26, priced at $268 found 1 day ago
Delta
Tue, Apr 15 - Wed, Apr 23
MCO
Orlando Intl.
MSN
Dane County Regional
$268 Roundtrip, found 23 hours ago
$268
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Apr 15 from Orlando Intl. to Dane County Regional, returning Wed, Apr 23, priced at $268 found 23 hours ago
American Airlines
Wed, Mar 12 - Tue, Mar 25
TUL
Tulsa Intl.
MSN
Dane County Regional
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 12 from Tulsa Intl. to Dane County Regional, returning Tue, Mar 25, priced at $269 found 1 day ago
American Airlines
Tue, Apr 15 - Wed, Apr 16
MCO
Orlando Intl.
MSN
Dane County Regional
$279 Roundtrip, found 23 hours ago
$279
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Apr 15 from Orlando Intl. to Dane County Regional, returning Wed, Apr 16, priced at $279 found 23 hours ago
Delta
Tue, Apr 15 - Mon, Apr 21
MCO
Orlando Intl.
MSN
Dane County Regional
$288 Roundtrip, found 23 hours ago
$288
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Apr 15 from Orlando Intl. to Dane County Regional, returning Mon, Apr 21, priced at $288 found 23 hours ago
American Airlines
Thu, Mar 13 - Tue, Mar 25
TUL
Tulsa Intl.
MSN
Dane County Regional
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Mar 13 from Tulsa Intl. to Dane County Regional, returning Tue, Mar 25, priced at $294 found 1 day ago
Breeze Airways
Sat, Jun 7 - Sat, Jun 21
MCO
Orlando Intl.
MSN
Dane County Regional
$323 Roundtrip, found 4 days ago
$323
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Jun 7 from Orlando Intl. to Dane County Regional, returning Sat, Jun 21, priced at $323 found 4 days ago
Frontier Airlines
Wed, Apr 16 - Thu, Apr 24
MCO
Orlando Intl.
MSN
Dane County Regional
$329 Roundtrip, found 23 hours ago
$329
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, Apr 16 from Orlando Intl. to Dane County Regional, returning Thu, Apr 24, priced at $329 found 23 hours ago
Delta
Tue, Feb 4 - Wed, Feb 12
PHL
Philadelphia Intl.
MSN
Dane County Regional
$489 Roundtrip, found 1 day ago
$489
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 4 from Philadelphia Intl. to Dane County Regional, returning Wed, Feb 12, priced at $489 found 1 day 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 April, 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 16 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 $217, 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 $217 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$438

Last Minute Hotel Deals in Highland

Don Q Inn
Don Q Inn
2.5 out of 5
3658 State Road 23, Dodgeville, WI
The price is $74 per night from Jan 26 to Jan 27
$74
includes taxes & fees
Jan 26 - Jan 27
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 ...
7.8/10 Good! (939 reviews)
"great place .great people. great service perfect place to get away for a weekend"

Reviewed on Jan 19, 2025

Don Q Inn
Deer Valley Lodge & Golf
Deer Valley Lodge & Golf
2.5 out of 5
401 West Industrial Drive, Barneveld, WI
The price is $94 per night from Jan 26 to Jan 27
$94
includes taxes & fees
Jan 26 - Jan 27
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! (563 reviews)
"Water park was fun after a long day of traveling. Clean, large room. Breakfast was good."

Reviewed on Jan 2, 2025

Deer Valley Lodge & Golf
AmericInn by Wyndham Dodgeville
AmericInn by Wyndham Dodgeville
2.5 out of 5
3637 State Road 23, Dodgeville, WI
The price is $108 per night from Feb 3 to Feb 4
$108
includes taxes & fees
Feb 3 - Feb 4
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! (463 reviews)
"So quiet and the views to the country are our outstanding"

Reviewed on Jan 4, 2025

AmericInn by Wyndham Dodgeville
AmericInn by Wyndham Boscobel
AmericInn by Wyndham Boscobel
2.5 out of 5
1700 Elm St, Boscobel, WI
The price is $85 per night from Jan 29 to Jan 30
$85
includes taxes & fees
Jan 29 - Jan 30
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! (399 reviews)
"Better than average continental breakfast, but the cream cheese needs to be refrigerated."

Reviewed on Dec 30, 2024

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
The price is $86 per night from Jan 30 to Jan 31
$86
includes taxes & fees
Jan 30 - Jan 31
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 ...
8.2/10 Very Good! (573 reviews)
"Friendly staff and very helpful"

Reviewed on Jan 7, 2025

Best Western Dodgeville Inn & Suites
Holiday Inn Express and Suites-Platteville, an IHG Hotel
Holiday Inn Express and Suites-Platteville, an IHG Hotel
2.5 out of 5
55 S ELM ST, Platteville, WI
The price is $134 per night from Feb 2 to Feb 3
$134
includes taxes & fees
Feb 2 - Feb 3
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! (476 reviews)
"By far, the best place to stay in Platteville. We’re always happy with the service —staff are welcoming, responsive and very friendly."

Reviewed on Jan 11, 2025

Holiday Inn Express and Suites-Platteville, an IHG Hotel
The Round Barn Lodge
The Round Barn Lodge
2.5 out of 5
E4830 Us Highway 14, Spring Green, WI
The price is $92 per night from Jan 26 to Jan 27
$92
includes taxes & fees
Jan 26 - Jan 27
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! (530 reviews)
"Such a great place! A must stay."

Reviewed on Jan 17, 2025

The Round Barn Lodge
Ramada by Wyndham Richland Center
Ramada by Wyndham Richland Center
3 out of 5
1450 Veterans Dr, Richland Center, WI
The price is $87 per night from Feb 2 to Feb 3
$87
includes taxes & fees
Feb 2 - Feb 3
Stay at this 3-star business-friendly hotel in Richland Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
8.2/10 Very Good! (551 reviews)
Find another place to stay
"Walked into a 45 degree room that took four hours to heat up, window sills and walls by shower are filthy, sign in elevator says no continental breakfast on fri/sat/sun but they had one, no garbage can in breakfast area, broken outlet cover in breakfast area, bottom safety handle in shower not attached, ..."

Reviewed on Jan 6, 2025

Ramada by Wyndham Richland Center
See all 116 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.