Cheap Flights to Highland: Highland Flight Deals

View €177 flight on Thu, 23 Jul 2026Opens in a new window

Popular airlines to Highland

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Cheap round-trip flights to Highland

Prices were available within the past 7 days and start at €177 for one-way flights and €209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, 29 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
€209 Return, found 1 day ago
€209
Return
found 1 day ago
Select United flight, departing Sat, 29 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at €209 found 1 day ago
American Airlines
Sat, 29 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
€265 Return, found 1 day ago
€265
Return
found 1 day ago
Select American Airlines flight, departing Sat, 29 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at €265 found 1 day ago
Delta
Fri, 21 Nov - Sun, 23 Nov
DUB
Dublin
MSN
Madison
€550 Return, found 4 days ago
€550
Return
found 4 days ago
Select Delta flight, departing Fri, 21 Nov from Dublin to Madison, returning Sun, 23 Nov, priced at €550 found 4 days ago
KLM
Wed, 19 Nov - Mon, 24 Nov
DUB
Dublin
MSN
Madison
€598 Return, found 6 days ago
€598
Return
found 6 days ago
Select KLM flight, departing Wed, 19 Nov from Dublin to Madison, returning Mon, 24 Nov, priced at €598 found 6 days ago
Air France
Wed, 19 Nov - Sun, 23 Nov
DUB
Dublin
MSN
Madison
€619 Return, found 2 days ago
€619
Return
found 2 days ago
Select Air France flight, departing Wed, 19 Nov from Dublin to Madison, returning Sun, 23 Nov, priced at €619 found 2 days ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

July is typically the cheapest month to fly

From €67 - €252 per traveller.

Frequently asked questions

What is the name of Highland's airport?
Highland has only one airport, Dane County Regional Airport (MSN).
What airport is best to fly into Highland?
With just one main airport in Highland, it won't take very long to get your hands on the best flight. You'll be jetting off to MSN, which sits around 88 kilometres from the centre of town.
How many airlines fly to Highland?
Highland is serviced by 5 air carriers from 16 airports around the world.
Which airlines fly to Highland?
United Airlines and American Airlines fly often into Highland. Catching a United Airlines flight from Chicago is one of the most popular ways to travel there.
How many nonstop flights are there to Highland?
Flying to a new place is much easier when there aren't any stopovers to worry about. If you're jetting off to Highland, the great news is that there are approximately 264 direct flights operating each week.
Where are the most popular flights to Highland departing from?
Flights to Highland from Chicago, Minneapolis - St. Paul and Detroit airports are very popular.
How long is the flight to Highland Airport?
If you're heading to Highland from Chicago, you're looking at a flight duration of 1 hour and 6 minutes. Those leaving from Minneapolis - St. Paul can expect to be travelling for 1 hour and 12 minutes. From Detroit it's roughly 1 hour and 27 minutes away.
How to book the cheapest flight to Highland?
If you want to save some cash on your Highland holiday, listen up! As every seasoned jet-setter knows, don't leave booking until the last minute. Prices are often highest just prior to the departure date. Also, shop around and compare your options. If your destination has more than one airport, you may be able to score a fantastic deal by flying into one that's further away. Lastly, another simple way to save some cash is be ready to book fast. If you see an amazing deal, don't hold off — grab it while you've got the chance.
Do you have any tips for my flight to Highland?
Depending on where you're coming from, your flight to Highland could be simple and straightforward or it could go on forever. We've pulled together some useful travel tips that will help you start your next great adventure on the right foot. What to pack in your hand luggage:

  • It's simple — first, put in your passport, important documents, credit cards and daily medications. Next, you'll want some in-flight entertainment to help pass the time. A juicy book and a tablet filled with your favourite shows are some fantastic options. If you plan to take a short nap, a comfy neck pillow and some noise-cancelling headphones will also be useful. Finally, find room for a toothbrush and some cleansing wipes so you'll arrive looking and feeling fresh.

Do not pack the following items in your hand luggage:

  • Put all your full-sized bottles of shampoo and hair gel in your checked baggage. Any liquids or gels in your carry-on suitcase larger than 3.4 ounces (100 millilitres) won't be allowed on. Sharp objects, like your precious Swiss Army knife, and dangerous goods which are flammable or explosive, such as spray paint, flares and matches, are also banned.

What to wear on a flight:

  • Comfort should be your top priority when choosing what to wear on your flight. Loose, breathable clothing is a smart option, as are enclosed shoes like sneakers.
  • Deep vein thrombosis (DVT), a blood clotting condition caused by lengthy periods of inactivity, can be a risk on long-haul flights. Try to walk around the cabin and stretch your legs or do some simple exercises in your seat to improve your circulation.

How to get through airport security fast when flying to Highland?
It's easy — be prepared. We've rounded up some top tips for a stress-free trip through security. Watch out Highland, here you come:

  • Security personnel first need to verify that you have a valid passport and matching travel documents before you're allowed to proceed any further. Have them ready to show.
  • After that, both you and your hand luggage must be X-rayed. To make the process quick and painless, remove anything that might trigger the alarms. Items such as your jacket, belt and earphones will be required to go through the machine.
  • All your electronic gadgets, including your tablet and phone, must also be scanned separately.
  • Remove liquids and gels from your carry-on luggage. They often need to be sent through the X-ray scanner separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a quart-size (one litre), clear zip-close bag.
  • The right choice of footwear can save you several minutes. Boots and bulky shoes are often required to be removed and separately scanned. Lightweight sneakers usually aren't.
  • Take all prohibited items out of your carry-on bag. If you have any sharp or pointed objects, put them in your checked baggage. They won't be allowed on board.

Book with confidence

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Highland. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Highland. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Highland, or are just on the lookout for the best flights to Highland, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Highland to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Travel information

Destination airport
Dane County Regional
Destination airport IATA code
MSN
Destination city name
Madison
Return price
€198

Trending flights to Highland

Prices were available within the past 7 days and start at €177 for one-way flights and €209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 21 Nov - Sun, 23 Nov
DUB
Dublin
MSN
Madison
€550 Return, found 4 days ago
€550
Return
found 4 days ago
Select Delta flight, departing Fri, 21 Nov from Dublin to Madison, returning Sun, 23 Nov, priced at €550 found 4 days ago

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