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Highland

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Highland Flights as Low as $279

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

Delta
Fri, Apr 25 - Fri, Apr 25
YYZ
Pearson Intl.
MSN
Dane County Regional
$279 Roundtrip, found 2 days ago
$279
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Apr 25 from Pearson Intl. to Dane County Regional, returning Fri, Apr 25, priced at $279 found 2 days ago
Air Canada
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $285 found 1 day ago
American Airlines
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $285 found 1 day ago
United
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $285 found 1 day ago
Delta
Sat, Apr 19 - Fri, Apr 25
YYZ
Pearson Intl.
MSN
Dane County Regional
$285 Roundtrip, found 2 days ago
$285
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 19 from Pearson Intl. to Dane County Regional, returning Fri, Apr 25, priced at $285 found 2 days ago
Delta
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$322 Roundtrip, found 1 day ago
$322
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $322 found 1 day ago
Air Canada
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $324 found 1 day ago
Delta
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $340 found 1 day ago
United
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$343 Roundtrip, found 1 day ago
$343
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $343 found 1 day ago
Delta
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$351 Roundtrip, found 1 day ago
$351
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $351 found 1 day ago
United
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $353 found 1 day ago
American Airlines
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$356 Roundtrip, found 1 day ago
$356
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $356 found 1 day ago
United
Tue, Apr 22 - Mon, Apr 28
YYZ
Pearson Intl.
MSN
Dane County Regional
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 22 from Pearson Intl. to Dane County Regional, returning Mon, Apr 28, priced at $358 found 1 day ago
American Airlines
Tue, Apr 1 - Tue, Apr 15
LAX
Los Angeles Intl.
LSE
La Crosse Municipal
$442 Roundtrip, found 5 hours ago
$442
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Apr 1 from Los Angeles Intl. to La Crosse Municipal, returning Tue, Apr 15, priced at $442 found 5 hours ago
American Airlines
Wed, Apr 16 - Mon, Apr 21
SEA
Seattle - Tacoma Intl.
LSE
La Crosse Municipal
$504 Roundtrip, found 3 days ago
$504
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Apr 16 from Seattle - Tacoma Intl. to La Crosse Municipal, returning Mon, Apr 21, priced at $504 found 3 days ago
American Airlines
Sun, Apr 20 - Fri, Apr 25
YYZ
Pearson Intl.
LSE
La Crosse Municipal
$578 Roundtrip, found 1 day ago
$578
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Apr 20 from Pearson Intl. to La Crosse Municipal, returning Fri, Apr 25, priced at $578 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 $279, 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 $279 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$217

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 $85 per night from Mar 26 to Mar 27
$85
includes taxes & fees
Mar 26 - Mar 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! (954 reviews)
"Unique rooms and historic themed areas"

Reviewed on Mar 23, 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 Apr 1 to Apr 2
$94
includes taxes & fees
Apr 1 - Apr 2
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! (574 reviews)
Great little Waterpark
"Friendly and helpful staff, good affordable family fun. The Waterpark was a big win."

Reviewed on Mar 18, 2025

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
The price is $131 per night from Apr 15 to Apr 16
$131
includes taxes & fees
Apr 15 - Apr 16
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! (488 reviews)
"This hotel is just about perfect. Staff is amazing... The rooms are very clean and comfortable."

Reviewed on Feb 27, 2025

Holiday Inn Express and Suites-Platteville by IHG
The Round Barn Lodge
The Round Barn Lodge
2.5 out of 5
E4830 Us Highway 14, Spring Green, WI
The price is $95 per night from Mar 30 to Mar 31
$95
includes taxes & fees
Mar 30 - Mar 31
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! (534 reviews)
"Rooms were spacious and clean. Had nice size fridge and microwave."

Reviewed on Feb 10, 2025

The Round Barn Lodge
AmericInn by Wyndham Dodgeville
AmericInn by Wyndham Dodgeville
2.5 out of 5
3637 State Road 23, Dodgeville, WI
The price is $106 per night from Apr 1 to Apr 2
$106
includes taxes & fees
Apr 1 - Apr 2
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! (469 reviews)
"Clean"

Reviewed on Feb 20, 2025

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
The price is $86 per night from Apr 6 to Apr 7
$86
includes taxes & fees
Apr 6 - Apr 7
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 ...
9.2/10 Wonderful! (201 reviews)
"Ever"

Reviewed on Mar 20, 2025

Sleep Inn & Suites Lancaster-Platteville
AmericInn by Wyndham Boscobel
AmericInn by Wyndham Boscobel
2.5 out of 5
1700 Elm St, Boscobel, WI
The price is $93 per night from Mar 31 to Apr 1
$93
includes taxes & fees
Mar 31 - Apr 1
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! (403 reviews)
"Better than average continental breakfast, but the cream cheese needs to be refrigerated."

Reviewed on Dec 30, 2024

AmericInn by Wyndham Boscobel
Ramada by Wyndham Richland Center
Ramada by Wyndham Richland Center
3 out of 5
1450 Veterans Dr, Richland Center, WI
The price is $84 per night from Apr 2 to Apr 3
$84
includes taxes & fees
Apr 2 - Apr 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! (556 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.