Cheap Flights to Highland Park , IL from CA $152

View CA $152 flight on Thu, Nov. 27, 2025Opens in a new window

Popular airlines to Highland Park

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How much is the cheapest flight to Highland Park?

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Nov. 27 - Mon, Dec. 1
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, just found
CA $243
Roundtrip
just found
Select Air Canada flight, departing Thu, Nov. 27 from Toronto to Chicago, returning Mon, Dec. 1, priced at CA $243 just found
United
Thu, Nov. 13 - Sun, Nov. 16
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, just found
CA $244
Roundtrip
just found
Select United flight, departing Thu, Nov. 13 from Toronto to Chicago, returning Sun, Nov. 16, priced at CA $244 just found
Porter Airlines
Tue, Aug. 12 - Wed, Sep. 3
YTZ
Toronto
MDW
Chicago
CA $249 Roundtrip, found 4 days ago
CA $249
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Tue, Aug. 12 from Toronto to Chicago, returning Wed, Sep. 3, priced at CA $249 found 4 days ago
American Airlines
Fri, Oct. 31 - Thu, Nov. 6
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, found 2 hours ago
CA $261
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Oct. 31 from Toronto to Chicago, returning Thu, Nov. 6, priced at CA $261 found 2 hours ago
Air Transat
Fri, Sep. 5 - Sat, Sep. 13
YTZ
Toronto
MDW
Chicago
CA $285 Roundtrip, found 4 days ago
CA $285
Roundtrip
found 4 days ago
Select Air Transat flight, departing Fri, Sep. 5 from Toronto to Chicago, returning Sat, Sep. 13, priced at CA $285 found 4 days ago

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

June is typically the cheapest month to fly

From CA $105 - CA $339 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Highland Park. 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 Highland Park. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Highland Park.

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 Highland Park 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 Highland Park.

Looking to save even more? Get additional savings by bundling your Highland Park 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 Highland Park trip!

Frequently asked questions

What is the name of Highland Park's airport?
Highland Park has several airports, but most visitors touch down at O'Hare Intl. Airport (ORD).
How far is O'Hare Airport from central Highland Park?
If you plan on staying in central Highland Park, it's wise to arrange how you'll get into the city before you arrive. The downtown area is 24 kilometres from O'Hare Intl. Airport (ORD).
What airport is best to fly into Highland Park?
Flying to Highland Park means stepping off the plane at either ORD or Midway Airport. The first is 24 kilometres away from the downtown area. The second one is 40 kilometres away.
How many airlines fly to Highland Park?
There are 51 airlines that jet into Highland Park from 237 worldwide airports.
Which airlines fly to Highland Park?
United Airlines, American Airlines and Delta are the most frequent fliers to Highland Park. The majority of flights come in from New York, with United Airlines having the most services on this route.
How many nonstop flights are there to Highland Park?
With approximately 7,564 direct flights running each week, you'll be hitting the tarmac in Highland Park before you can ask, "Are we there yet?"
Where are the most popular flights to Highland Park departing from?
A large number of flights to Highland Park set off from New York, Washington and Dallas airports.
How long is the flight to Highland Park Airport?
If you're flying to Highland Park from New York, you'll have a flight time of 2 hours and 44 minutes. Those setting off from Washington can expect to be airborne for 2 hours and 15 minutes. From Dallas it's around 2 hours and 18 minutes away.
How to book the cheapest flight to Highland Park?
We've all come across those jet-setters who somehow manage to score incredibly cheap airfares whenever they fly. Would you like to know how to do it for your Highland Park vacation? Don't leave it until the very last minute to secure your flight. Another great way to get an unbeatable deal is to research all options. If your destination has multiple airports, don't forget to research the cost of flying into a less busy terminal. And finally, remember that the early bird catches the worm. Familiarize yourself with airfare costs and be ready to snap up a ticket as soon as you spot an unbeatable bargain. The sweetest deals don't last long.
Do you have any tips for my flight to Highland Park?
No matter where you're coming from, flying can be a seamless experience if you've prepared well. We've made a list of handy tips that will get your Highland Park escape started on the right note. What to pack in your hand luggage:

  • The secret to having a worry-free travel experience is to pack in advance. So, let's start with the essentials: passport, travel documents, cash and medications. Next, take on board items that'll help keep you busy, like some electronic devices or a good read. You'll also want to pack your chargers, a comfy neck pillow and a pair of earplugs. Finally, be sure to chuck in toiletries like a toothbrush, cleansing wipes and a spare change of clothes.

Do not pack the following items in your hand luggage:

  • While the list of restricted items differs between air carriers, the general rule to follow is avoid carrying anything flammable, sharp or explosive. This includes box cutters, razor blades, fuel and fireworks. Sporting equipment like hockey sticks, and items that could injure passengers, such as swords and batons, can't come on board with you either.

What to wear on a flight:

  • The aisles of a plane are no place for a fashion parade. Layer up with comfy clothing and opt for shoes that are flat, enclosed and easy to slip on and off.
  • Deep vein thrombosis (DVT) is a risk on long-haul flights. It's the result of blood clotting due to inactivity and poor circulation, so do some gentle foot and leg exercises in your seat and consider wearing compression socks.

How to get through airport security fast when flying to Highland Park?
As seasoned travellers know, the secret is to be prepared before you arrive at the security gate. That way, you'll be stepping onto that plane to Highland Park in the blink of an eye. Follow these helpful tips and get your vacation off to a great start:

  • Have your boarding pass and ID easily accessible. They're the first things you'll be asked for by airport security.
  • Time to strip down. Well kind of. Your belt, jacket, keys and other contents of your pockets, like coins, will need to go on a tray through the X-ray machine. Make your life easier by removing them before your turn arrives.
  • Your electronic gadgets like phones and laptops will also have to go through the machine to be scanned. No need to worry though, you'll be back online soon enough.
  • Don't forget to remove gels and liquids from your carry-on bag. They often 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-close bag.
  • The right choice of footwear can save you several minutes. Hiking or heavy-style boots are often required to be removed and separately scanned. Slip-on sneakers are usually not.
  • Airlines won't allow any sharp items or pocket knives in your carry-on luggage. If you must bring these kinds of items, pack them safely in your checked baggage.

Flights to Highland Park information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $243

Trending flights to Highland Park

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Wed, Oct. 8 - Wed, Oct. 8
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, found 10 hours ago
CA $243
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Wed, Oct. 8 from Toronto to Chicago, returning Wed, Oct. 8, priced at CA $243 found 10 hours ago
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