Search Cheap Flights to
Highland

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Flights as Low as $211

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

Frontier Airlines
Sat, Oct 10 - Sat, Oct 24
LAS
Harry Reid Intl.
MSN
Dane County Regional
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Harry Reid Intl. to Dane County Regional, returning Sat, Oct 24, priced at $211 found 1 day ago
Frontier Airlines
Sat, Oct 10 - Wed, Oct 21
LAS
Harry Reid Intl.
MSN
Dane County Regional
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Harry Reid Intl. to Dane County Regional, returning Wed, Oct 21, priced at $222 found 1 day ago
Frontier Airlines
Sat, Sep 12 - Sun, Sep 27
LAS
Harry Reid Intl.
MSN
Dane County Regional
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Harry Reid Intl. to Dane County Regional, returning Sun, Sep 27, priced at $234 found 1 day ago
Frontier Airlines
Thu, Oct 1 - Sat, Oct 17
SFO
San Francisco Intl.
MSN
Dane County Regional
$235 Roundtrip, found 16 hours ago
$235
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, Oct 1 from San Francisco Intl. to Dane County Regional, returning Sat, Oct 17, priced at $235 found 16 hours ago
Frontier Airlines
Sat, Oct 10 - Fri, Oct 23
LAS
Harry Reid Intl.
MSN
Dane County Regional
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Harry Reid Intl. to Dane County Regional, returning Fri, Oct 23, priced at $238 found 1 day ago
Bargain Flight
Thu, Oct 1 - Fri, Oct 9
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Oct 1 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Oct 9, priced at $240 found 1 day ago
Frontier Airlines
Sun, Sep 6 - Thu, Sep 17
LAS
Harry Reid Intl.
MSN
Dane County Regional
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Harry Reid Intl. to Dane County Regional, returning Thu, Sep 17, priced at $250 found 1 day ago
Frontier Airlines
Sat, Oct 10 - Sat, Oct 24
LAS
Harry Reid Intl.
MSN
Dane County Regional
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Harry Reid Intl. to Dane County Regional, returning Sat, Oct 24, priced at $253 found 1 day ago
Frontier Airlines
Thu, Oct 1 - Fri, Oct 16
SFO
San Francisco Intl.
MSN
Dane County Regional
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 1 from San Francisco Intl. to Dane County Regional, returning Fri, Oct 16, priced at $254 found 1 day ago
Bargain Flight
Thu, Aug 20 - Tue, Aug 25
BOS
Logan Intl.
MSN
Dane County Regional
$285 Roundtrip, found 5 days ago
$285
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Thu, Aug 20 from Logan Intl. to Dane County Regional, returning Tue, Aug 25, priced at $285 found 5 days ago
Frontier Airlines
Sun, Aug 23 - Thu, Aug 27
MCO
Orlando Intl.
MSN
Dane County Regional
$299 Roundtrip, found 19 hours ago
$299
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sun, Aug 23 from Orlando Intl. to Dane County Regional, returning Thu, Aug 27, priced at $299 found 19 hours ago
Delta
Tue, Oct 13 - Sat, Oct 24
LAS
Harry Reid Intl.
MSN
Dane County Regional
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 13 from Harry Reid Intl. to Dane County Regional, returning Sat, Oct 24, priced at $307 found 1 day ago
American Airlines
Thu, Oct 1 - Tue, Oct 13
BGR
Bangor Intl.
MSN
Dane County Regional
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 1 from Bangor Intl. to Dane County Regional, returning Tue, Oct 13, priced at $309 found 1 day ago
Breeze Airways
Wed, Aug 26 - Sat, Aug 29
MCO
Orlando Intl.
MSN
Dane County Regional
$324 Roundtrip, found 19 hours ago
$324
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Dane County Regional, returning Sat, Aug 29, priced at $324 found 19 hours ago
Delta
Tue, Oct 27 - Sat, Nov 14
FCA
Glacier Park Intl.
MSN
Dane County Regional
$359 Roundtrip, found 15 hours ago
$359
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Oct 27 from Glacier Park Intl. to Dane County Regional, returning Sat, Nov 14, priced at $359 found 15 hours ago
Alaska Airlines
Wed, Sep 2 - Tue, Sep 8
LAS
Harry Reid Intl.
MSN
Dane County Regional
$565 Roundtrip, found 2 days ago
$565
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Sep 2 from Harry Reid Intl. to Dane County Regional, returning Tue, Sep 8, priced at $565 found 2 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 October, 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 $211, 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 $211 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$211

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)
"We enjoyed the experience and had fun, however the room was outdated and needed some work. We were in the Blue Room. But overall I would definitely do it again for the memories we made and the laughter we had while there! Just know that there will be some flaws."

Reviewed on Aug 11, 2026

Get rates
Don Q Inn
Dodgeville inn and suites

Dodgeville inn and suites

2.5 out of 5
1308 n johns st Dodgeville WI
Stay at this hotel in Dodgeville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cox Hollow Beach and Governor Dodge State Park are located ...
7.2/10 Good! (83 reviews)
"The beds were terrible. Woke up with bad back pain. There was no pool or hot tub. Breakfast was not great. Juice was warm or non existent. Door leading up to place had swipe reader broken on it. Would not recommend staying there."

Reviewed on Aug 11, 2026

Get rates
Dodgeville inn and suites
AmericInn by Wyndham Dodgeville

AmericInn by Wyndham Dodgeville

3 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! (626 reviews)
"Very friendly employees!"

Reviewed on Aug 6, 2026

Get rates
AmericInn by Wyndham Dodgeville
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! (351 reviews)
"Property well cared for. Staff friendly and helpful when needed."

Reviewed on Aug 10, 2026

Get rates
Sleep Inn & Suites Lancaster-Platteville
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 ...
8.6/10 Excellent! (670 reviews)
"It was very nice, clean, good location for seeing APT, Taliesin etc. The pool was clean and pleasant, and I liked waking up to see the field of solar panels across from the parking lot. There's a nice breakfast place down the road. It would be great if they added an EV charger!"

Reviewed on Aug 12, 2026

Get rates
The Round Barn Lodge
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! (724 reviews)
"We stayed here because of an event our family had in Barneveld, WI. It was good. The linens were a bit tired but clean. The pool and hot tub were kept decently clean though the kids on the weekends pretty much took the place over. The staff were helpful with what the area had to offer. I would stay ..."

Reviewed on Aug 10, 2026

Get rates
Deer Valley Lodge & Golf
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! (724 reviews)
"The restaurant had no nachos and my son’s room had pink mold on walls"

Reviewed on Aug 11, 2026

Get rates
Ramada by Wyndham Richland Center
Spring Valley Inn

Spring Valley Inn

2.5 out of 5
6279 County Road C Arena WI
Book a stay at this business-friendly hotel in Arena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (442 reviews)
"Admired the efforts made to have the property reflect the APT and Wright designs. Efficient use of space in rooms, sustainable practices, and very pleasant staff. Loved the pool and hot tub. Close to theater for evening performances!"

Reviewed on Aug 10, 2026

Get rates
Spring Valley Inn
See all 125 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.