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Highland

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Highland Flights as Low as $203

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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 March, 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 $203, 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 $203 right now, why wait?

Highland Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$203

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)
Staff were friendly and available. Place was clean. Good for the price.

Reviewed on Jan 12, 2026

Don Q Inn
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! (678 reviews)
Fun!

Reviewed on Jan 17, 2026

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! (574 reviews)
Clean, comfortable rooms, covered parking, nice staff.

Reviewed on Jan 12, 2026

Holiday Inn Express and Suites-Platteville by IHG
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 ...
8.2/10 Very Good! (655 reviews)
Everything is fantastic at this hotel. We will be back.

Reviewed on Jan 8, 2026

Ramada by Wyndham Richland Center
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 ...
9.2/10 Wonderful! (280 reviews)
Friendly staff , clean rooms clean hotel since the moment you walk in .

Reviewed on Jan 23, 2026

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 ...
8.2/10 Very Good! (572 reviews)
Not much to say about the property. Clean and kept up.

Reviewed on Nov 27, 2025

AmericInn by Wyndham Dodgeville
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! (473 reviews)
clean room, great service & good options for breakfast

Reviewed on Jan 19, 2026

AmericInn by Wyndham Boscobel
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! (620 reviews)
Great place to stay, the day before House On The Rock.

Reviewed on Jan 12, 2026

The Round Barn Lodge
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.