Cheap Flights to Highwood , IL from CA $143

View CA $143 flight on Thu, Aug. 28, 2025Opens in a new window

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How much is the cheapest flight to Highwood?

Prices were available within the past 7 days and start at CA $143 for one-way flights and CA $226 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, Aug. 29 - Sun, Aug. 31
YTZ
Toronto
MDW
Chicago
CA $226 Roundtrip, just found
CA $226
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Aug. 29 from Toronto to Chicago, returning Sun, Aug. 31, priced at CA $226 just found
Air Canada
Thu, Nov. 27 - Mon, Dec. 1
YTZ
Toronto
ORD
Chicago
CA $226 Roundtrip, found 1 hour ago
CA $226
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Thu, Nov. 27 from Toronto to Chicago, returning Mon, Dec. 1, priced at CA $226 found 1 hour ago
United
Wed, Sep. 3 - Sun, Sep. 14
YYZ
Toronto
ORD
Chicago
CA $235 Roundtrip, just found
CA $235
Roundtrip
just found
Select United flight, departing Wed, Sep. 3 from Toronto to Chicago, returning Sun, Sep. 14, priced at CA $235 just found
American Airlines
Wed, Nov. 26 - Tue, Dec. 2
YYZ
Toronto
ORD
Chicago
CA $260 Roundtrip, just found
CA $260
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov. 26 from Toronto to Chicago, returning Tue, Dec. 2, priced at CA $260 just found
Air Transat
Fri, Aug. 29 - Sun, Aug. 31
YTZ
Toronto
MDW
Chicago
CA $268 Roundtrip, just found
CA $268
Roundtrip
just found
Select Air Transat flight, departing Fri, Aug. 29 from Toronto to Chicago, returning Sun, Aug. 31, priced at CA $268 just found

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

June is typically the cheapest month to fly

From CA $106 - CA $340 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Highwood. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Highwood. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Highwood.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Highwood flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Highwood.

Looking to save even more? Get additional savings by bundling your Highwood flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Highwood trip!

Frequently asked questions

What is the name of Highwood's airport?
Book a flight to Highwood and you'll be hitting the tarmac at O'Hare Intl. Airport (ORD).
How far is ORD from central Highwood?
Long commutes don't have to be stressful if you consider your options ahead of time. Downtown Highwood is 27 kilometres from O'Hare Intl. Airport (ORD), so it's wise to know how to get to the city before you land.
What airport is best to fly into Highwood?
Sitting 27 kilometres from the centre of town, O'Hare Airport is likely to be your first stop in Highwood.
How many airlines fly to Highwood?
Highwood is serviced by 49 airlines from at least 224 airports across the globe.
Which airlines fly to Highwood?
Highwood receives the largest number of flights from United Airlines, American Airlines and Delta with United Airlines being the preferred choice of airline. New York is the most popular city for passengers to take off from.
How many nonstop flights are there to Highwood?
With roughly 6,379 direct flights every week, you'll be arriving in Highwood before you can say, "Are we there yet?"
Where are the most popular flights to Highwood departing from?
Flights to Highwood departing from New York, Washington and Dallas airports are highly sought after.
How long is the flight to Highwood Airport?
If you're going to Highwood from New York, you'll have a flight time of 2 hours and 48 minutes. Those taking off from Washington should expect to be airborne for around 2 hours and 18 minutes. From Dallas it's roughly 2 hours and 23 minutes away.
How to book the cheapest flight to Highwood?
We all know those fortunate jet-setters who manage to score incredibly cheap fares wherever they go. Want to know how to do it for your Highwood vacation? Don't wait until the last moment to lock in your flight. Don't stop there, however. Do some research and check if there are a few airports at your destination. Prices often differ depending on which airport you jet into. Don't forget to compare prices across airlines too. Last but not least, be prepared to secure your seat quickly if you stumble on a great deal. It might not stick around for too long. With a bit of know-how and some luck, the perfect fare can be yours.
Do you have any tips for my flight to Highwood?
Depending on where you're coming from, your journey to Highwood could be a breeze or it could go on forever. We've compiled some handy travel tips that will help you start your next unforgettable escape on a positive note. What to pack in your hand luggage:

  • First of all, pack in your passport, travel documents, credit cards and medications. Next, you'll want some extra in-flight entertainment to while away the time. A thrilling book and a phone crammed with your favourite movies are some fantastic options. If you intend to catch forty winks, a neck pillow and a pair of noise-cancelling headphones will also be useful. Finally, find room for a toothbrush and some deodorant to ensure you hop off the plane feeling fresh and ready to go.

Do not pack the following items in your hand luggage:

  • Pack 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) won't be allowed on. Sharp objects, like your precious pocket knife, and products which are explosive or flammable, such as aerosol cans, spray paint and gasoline, are also not allowed.

What to wear on a flight:

  • You'll want to go for comfort over style. Prepare for temperature changes in the cabin by donning layers, and pick easy-to-remove footwear like slip-ons.
  • Caused by lengthy periods of inactivity, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers during long flights. Lower your risks by staying hydrated, keeping your legs and ankles moving and wearing compression socks to help improve your circulation.

How to get through airport security fast when flying to Highwood?
Being organized before you arrive at the airport will make your trip to Highwood a breeze. Read through our top tips for a swift journey past security:

  • First things first. Your travel ID and boarding pass will need to be presented to security personnel. Keep them someplace accessible so you don't have to dig around for them.
  • The X-ray machine comes next. Empty your pockets and remove anything that is likely to set off the alarm. This includes things like headphones or earphones, as well as your coat or jacket. They'll all need to go on the X-ray conveyor belt.
  • Your electronic devices like laptops and phones will also need to go on a tray for inspection. Don't worry, you'll be back online before you know it.
  • Travelling with your favourite perfume? As long as the volume is no larger than 3.4 ounces (100 millilitres) and it's stored in a clear zip-lock bag, you can bring it with you in your carry-on.
  • There's a possibility that you'll need to take your shoes off to be X-rayed, so wearing lightweight sneakers is always a good idea.
  • Take all prohibited items out of your carry-on bag. If you have any sharp objects like a pocket knife or tools, put them in your checked suitcase. They won't be allowed on board and will be confiscated.

Flights to Highwood information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $225

Trending flights to Highwood

Prices were available within the past 7 days and start at CA $143 for one-way flights and CA $226 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, Aug. 29 - Sun, Aug. 31
YTZ
Toronto
MDW
Chicago
CA $226 Roundtrip, just found
CA $226
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Aug. 29 from Toronto to Chicago, returning Sun, Aug. 31, priced at CA $226 just found
*Available to Expedia members.