Cheap Flights to Highland: Highland Flight Deals

View €248 flight on Tue, 25 Nov 2025Opens 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 €248 for one-way flights and €344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Icelandair
Fri, 9 Jan - Sun, 11 Jan
DUB
Dublin
ORD
Chicago
€344 Return, just found
€344
Return
just found
Select Icelandair flight, departing Fri, 9 Jan from Dublin to Chicago, returning Sun, 11 Jan, priced at €344 just found
TAP Portugal
Fri, 21 Nov - Fri, 28 Nov
DUB
Dublin
ORD
Chicago
€353 Return, found 8 hours ago
€353
Return
found 8 hours ago
Select TAP Portugal flight, departing Fri, 21 Nov from Dublin to Chicago, returning Fri, 28 Nov, priced at €353 found 8 hours ago
Scandinavian Airlines
Thu, 20 Nov - Thu, 27 Nov
DUB
Dublin
ORD
Chicago
€363 Return, found 5 days ago
€363
Return
found 5 days ago
Select Scandinavian Airlines flight, departing Thu, 20 Nov from Dublin to Chicago, returning Thu, 27 Nov, priced at €363 found 5 days ago
Aer Lingus
Sat, 1 Nov - Fri, 7 Nov
DUB
Dublin
ORD
Chicago
€363 Return, found 1 hour ago
€363
Return
found 1 hour ago
Select Aer Lingus flight, departing Sat, 1 Nov from Dublin to Chicago, returning Fri, 7 Nov, priced at €363 found 1 hour ago
American Airlines
Tue, 23 Dec - Sat, 3 Jan
DUB
Dublin
ORD
Chicago
€385 Return, found 1 hour ago
€385
Return
found 1 hour ago
Select American Airlines flight, departing Tue, 23 Dec from Dublin to Chicago, returning Sat, 3 Jan, priced at €385 found 1 hour ago

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

July is typically the cheapest month to fly

From €66 - €224 per traveller.

Frequently asked questions

What is the name of Highland's airport?
Highland has more than one airport, but most visitors prefer to touch down at O'Hare Intl. Airport (ORD).
What airport is best to fly into Highland?
Disembark the plane at O'Hare Intl. Airport (ORD) and you'll be 56 kilometres from the centre of town. Midway Intl. Airport (MDW) is another major airport in Highland. You'll find it 32 kilometres from the centre of the city.
How many airlines fly to Highland?
There are 51 air carriers connecting Highland with 237 airports across the globe.
Which airlines fly to Highland?
In general, travellers opt to fly with United Airlines, American Airlines and Delta when heading to Highland. The majority of these flights arrive from New York, with United Airlines flying this route the most.
How many nonstop flights are there to Highland?
Flying to a new place is much easier when there aren't any annoying stopovers to slow you down. If you're making your way to Highland, the good news is that there are around 7,564 nonstop flights operating each week.
Where are the most popular flights to Highland departing from?
Flights to Highland from New York, Washington and Dallas airports are always popular.
How long is the flight to Highland Airport?
If it's New York you're departing, you'll be airborne for around 2 hours and 44 minutes before you touchdown in Highland. Tarmac to tarmac from Washington takes approximately 2 hours and 15 minutes and from Dallas, the flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Highland?
Don't leave locking in your flight to Highland until the very last minute. That's one trick frequent jet-setters use to get the best prices. Booking well in advance means more options and less expensive flights. Don't stop there, however. Do some research and see if there is more than one airport at your destination. Ticket prices often differ depending on the airport you fly into. Be sure to compare prices across airlines as well. And finally, don't forget that it's first in, best dressed. Familiarise yourself with airfare costs and have your credit card ready to reserve your seat as soon as you see a great bargain. The sweetest deals don't last long.
Do you have any tips for my flight to Highland?
Depending on where you're coming from, your journey to Highland could be simple and straightforward or it could drag on forever. Here are some handy tips that will help you start your next great escape on a positive note. What to pack in your hand luggage:

  • The trick to having a hassle-free flight experience is to plan ahead. So, let's start with the basics: passport, travel documents, credit cards and any vital medications. Next, bring on board items that'll help keep you occupied, like some electronic gadgets or a few magazines. It's also wise to pack your chargers, a neck pillow and a pair of noise-cancelling headphones. Finally, be sure to toss in toiletry items like a toothbrush, cleansing wipes and a fresh set of clothes.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of shampoo and hairspray in your checked luggage. Any liquids or gels in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated by security. Pointed or sharp objects, like your pocket knife, and products which are explosive or flammable, such as spray paint, flares and strong acids, are also not allowed.

What to wear on a flight:

  • Go for comfort over style. Prepare for temperature changes in the cabin by dressing in layers, and opt for flat, slightly roomy footwear like sneakers.
  • Caused by sustained periods of immobility, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers during long-haul flights. Reduce the risks by drinking water, keeping your lower limbs moving and wearing compression tights or socks.

How to get through airport security fast when flying to Highland?
It's all about being organised. We've rounded up some helpful hints for an easy trip through security. Watch out Highland, here you come:

  • First things first. Your passport and travel documents will need to be shown to airport security personnel. Keep them within easy reach to avoid fumbling around for them.
  • The X-ray machine comes next. Remove anything metal on you that is likely to set off the scanner's alarm. This includes items like earphones or headphones, as well as your coat or jacket. They'll need to be placed on the conveyor belt for screening.
  • All electronic gadgets, including your tablet and phone, are also required to be separately scanned.
  • Remove all gels and liquids from your carry-on bag. They usually need to be sent through the X-ray machine separately. Each item should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit in a single quart-size (one litre), clear zip-lock bag.
  • There's a chance you'll need to take your shoes off to be X-rayed, so wearing slip-on shoes is always a smart idea.
  • Take all prohibited items out of your carry-on bag. If you have any sharp objects like a pocket knife or tools, pack them in your checked suitcase. They won't be allowed on board.

Book with confidence

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

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
€118

Trending flights to Highland

Prices were available within the past 7 days and start at €248 for one-way flights and €344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Icelandair
Fri, 9 Jan - Sun, 11 Jan
DUB
Dublin
ORD
Chicago
€344 Return, just found
€344
Return
just found
Select Icelandair flight, departing Fri, 9 Jan from Dublin to Chicago, returning Sun, 11 Jan, priced at €344 just found

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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