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 $184

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

Bargain Flight
Tue, Oct 14 - Sat, Oct 25
CMH
John Glenn Columbus Intl.
MSN
Dane County Regional
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Oct 14 from John Glenn Columbus Intl. to Dane County Regional, returning Sat, Oct 25, priced at $184 found 1 day ago
Bargain Flight
Sat, Aug 9 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
MSN
Dane County Regional
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Sat, Aug 9 from Charlotte-Douglas Intl. to Dane County Regional, returning Tue, Aug 12, priced at $217 found 6 days ago
American Airlines
Thu, Oct 30 - Sat, Nov 1
STL
Lambert-St. Louis Intl.
MSN
Dane County Regional
$229 Roundtrip, found 5 days ago
$229
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Oct 30 from Lambert-St. Louis Intl. to Dane County Regional, returning Sat, Nov 1, priced at $229 found 5 days ago
Delta
Thu, Aug 21 - Tue, Aug 26
CMH
John Glenn Columbus Intl.
MSN
Dane County Regional
$229 Roundtrip, found 9 hours ago
$229
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Aug 21 from John Glenn Columbus Intl. to Dane County Regional, returning Tue, Aug 26, priced at $229 found 9 hours ago
Delta
Wed, Aug 20 - Tue, Aug 26
CMH
John Glenn Columbus Intl.
MSN
Dane County Regional
$232 Roundtrip, found 9 hours ago
$232
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Aug 20 from John Glenn Columbus Intl. to Dane County Regional, returning Tue, Aug 26, priced at $232 found 9 hours ago
Delta
Tue, Aug 19 - Tue, Aug 26
CMH
John Glenn Columbus Intl.
MSN
Dane County Regional
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Aug 19 from John Glenn Columbus Intl. to Dane County Regional, returning Tue, Aug 26, priced at $237 found 9 hours ago
Bargain Flight
Tue, Oct 7 - Sat, Oct 11
SLC
Salt Lake City Intl.
MSN
Dane County Regional
$244 Roundtrip, found 20 hours ago
$244
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Tue, Oct 7 from Salt Lake City Intl. to Dane County Regional, returning Sat, Oct 11, priced at $244 found 20 hours ago
Frontier Airlines
Mon, Oct 6 - Thu, Oct 9
SLC
Salt Lake City Intl.
MSN
Dane County Regional
$258 Roundtrip, found 20 hours ago
$258
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Mon, Oct 6 from Salt Lake City Intl. to Dane County Regional, returning Thu, Oct 9, priced at $258 found 20 hours ago
Bargain Flight
Thu, Aug 21 - Sat, Aug 23
SAN
San Diego Intl.
MSN
Dane County Regional
$260 Roundtrip, found 4 days ago
$260
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Thu, Aug 21 from San Diego Intl. to Dane County Regional, returning Sat, Aug 23, priced at $260 found 4 days ago
Frontier Airlines
Thu, Sep 18 - Fri, Sep 19
SFO
San Francisco Intl.
MSN
Dane County Regional
$273 Roundtrip, found 18 hours ago
$273
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Sep 18 from San Francisco Intl. to Dane County Regional, returning Fri, Sep 19, priced at $273 found 18 hours ago
American Airlines
Fri, Aug 22 - Sun, Aug 24
CLD
McClellan-Palomar
MSN
Dane County Regional
$294 Roundtrip, found 4 days ago
$294
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Aug 22 from McClellan-Palomar to Dane County Regional, returning Sun, Aug 24, priced at $294 found 4 days ago
American Airlines
Fri, Oct 31 - Wed, Nov 5
CLT
Charlotte-Douglas Intl.
MSN
Dane County Regional
$297 Roundtrip, found 6 days ago
$297
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Oct 31 from Charlotte-Douglas Intl. to Dane County Regional, returning Wed, Nov 5, priced at $297 found 6 days ago
American Airlines
Tue, Sep 16 - Sat, Sep 20
SAN
San Diego Intl.
DBQ
Dubuque Regional
$444 Roundtrip, found 2 days ago
$444
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 16 from San Diego Intl. to Dubuque Regional, returning Sat, Sep 20, priced at $444 found 2 days ago
American Airlines
Sat, Sep 13 - Tue, Sep 23
SAN
San Diego Intl.
LSE
La Crosse Municipal
$452 Roundtrip, found 6 days ago
$452
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Sep 13 from San Diego Intl. to La Crosse Municipal, returning Tue, Sep 23, priced at $452 found 6 days ago
American Airlines
Tue, Oct 21 - Wed, Oct 29
SFO
San Francisco Intl.
LSE
La Crosse Municipal
$454 Roundtrip, found 1 day ago
$454
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 21 from San Francisco Intl. to La Crosse Municipal, returning Wed, Oct 29, priced at $454 found 1 day ago
American Airlines
Sat, Aug 2 - Sat, Aug 9
CLT
Charlotte-Douglas Intl.
DBQ
Dubuque Regional
$790 Roundtrip, found 3 days ago
$790
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Aug 2 from Charlotte-Douglas Intl. to Dubuque Regional, returning Sat, Aug 9, priced at $790 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 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 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 $184, 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 $184 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$272

Last Minute Hotel Deals in Highland

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! (518 reviews)
"The rooms were clean. Price was very good. The breakfast was good."

Reviewed on Jul 14, 2025

Get rates
AmericInn by Wyndham Dodgeville
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! (1,005 reviews)
"The rooms were clean and the lounge was unique with barber chairs. The plane outside looked neat too."

Reviewed on Jul 13, 2025

Get rates
Don Q Inn
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! (566 reviews)
Our Visit to Taliesan
"Basic rustic motel. Rooms were clean and well equipped. Coffee offerings in the am but found Anita's just down that the road has a good breakfast at a reasonable price. Staff assisted with getting us, two couples, downstairs rooms which was nice for us."

Reviewed on Jul 23, 2025

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! (630 reviews)
"Pleasantly surprised, for a non-chain facility. They did have an attached waterpark, which I did not use, but people seem to enjoy it. Breakfast is also pretty good."

Reviewed on Jul 28, 2025

Get rates
Deer Valley Lodge & Golf
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! (529 reviews)
"Exceptional service/ staff and clean !"

Reviewed on Jul 29, 2025

Get rates
Holiday Inn Express and Suites-Platteville by IHG
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! (613 reviews)
"Great location to see House on the Rock. Clean and quiet"

Reviewed on Jul 21, 2025

Get rates
Best Western Dodgeville Inn & Suites
Super 8 by Wyndham Dodgeville

Super 8 by Wyndham Dodgeville

2 out of 5
1308 N Johns St, 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 in our reviews. ...
7.6/10 Good! (786 reviews)
"Very polite, clean, and helpful!! Thanks!"

Reviewed on Jul 28, 2025

Get rates
Super 8 by Wyndham Dodgeville
Quality Inn & Suites Belmont Route 151

Quality Inn & Suites Belmont Route 151

2.5 out of 5
103 W Mound View Avenue, Belmont, WI
Book a stay at this business-friendly hotel in Belmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
8.2/10 Very Good! (230 reviews)
"Excellent"

Reviewed on Jul 20, 2025

Get rates
Quality Inn & Suites Belmont Route 151
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.