A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Cheap Flights to Hillside , IL from CA $203

View CA $203 flight on Wed, Sep 2, 2026Opens in a new window

Popular airlines to Hillside

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How much is the cheapest flight to Hillside?

Prices were available within the past 7 days and start at CA $203 for one-way flights and CA $344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Mon, Sep 14 - Thu, Sep 17
YTZ
Toronto
ORD
Chicago
CA $344 Roundtrip, just found
CA $344
Roundtrip
just found
Select Air Canada flight, departing Mon, Sep 14 from Toronto to Chicago, returning Thu, Sep 17, priced at CA $344 just found
Porter Airlines
Wed, Sep 2 - Mon, Sep 7
YTZ
Toronto
ORD
Chicago
CA $344 Roundtrip, just found
CA $344
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Sep 2 from Toronto to Chicago, returning Mon, Sep 7, priced at CA $344 just found
American Airlines
Fri, Sep 4 - Tue, Sep 8
YYZ
Toronto
ORD
Chicago
CA $356 Roundtrip, just found
CA $356
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep 4 from Toronto to Chicago, returning Tue, Sep 8, priced at CA $356 just found
Delta
Fri, Sep 4 - Tue, Sep 8
YYZ
Toronto
ORD
Chicago
CA $364 Roundtrip, just found
CA $364
Roundtrip
just found
Select Delta flight, departing Fri, Sep 4 from Toronto to Chicago, returning Tue, Sep 8, priced at CA $364 just found
Air Transat
Mon, Nov 23 - Sat, Nov 28
YTZ
Toronto
ORD
Chicago
CA $384 Roundtrip, found 4 days ago
CA $384
Roundtrip
found 4 days ago
Select Air Transat flight, departing Mon, Nov 23 from Toronto to Chicago, returning Sat, Nov 28, priced at CA $384 found 4 days ago

Frequently asked questions

What is the name of Hillside's airport?
O'Hare Intl. Airport (ORD) is the main airport in Hillside.
How far is ORD from central Hillside?
If you're staying in central Hillside, it's a good idea to work out how you'll get into the city before you touchdown. The downtown area is about 11 kilometres from O'Hare Airport.
What airport is best to fly into Hillside?
Before flying to Hillside, it's a smart idea to find out which airport is the most convenient. O'Hare Airport is 11 kilometres from the downtown area. If you're landing at Midway Airport, you'll find yourself 16 kilometres away from the city centre.
How many airlines fly to Hillside?
There are 51 airlines connecting Hillside to 237 airports from all over the globe.
Which airlines fly to Hillside?
Most often, travellers opt to fly with United Airlines, American Airlines and Delta when heading to Hillside. The largest number of these flights originate in New York, with United Airlines servicing this route the most frequently.
How many nonstop flights are there to Hillside?
Organizing an unforgettable Hillside getaway is a walk in the park when there are 7,564 nonstop flights each week to choose from.
Where are the most popular flights to Hillside departing from?
The most popular flights to Hillside leave from New York, Washington and Dallas airports.
How long is the flight to Hillside Airport?
Which city you depart from determines how much of the in-flight entertainment you'll get to see. From New York to Hillside, the average flight time is 2 hours and 44 minutes. From Washington it takes about 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Hillside?
Don't leave locking in your flight to Hillside until the last possible moment. That's one trick frequent jet-setters use to get the best prices. Booking in advance means more options and less expensive flights. Don't stop there, though. Do some research and find out if there are a few airports at your destination. Ticket prices often differ depending on which airport you pick. Don't forget to compare prices across air carriers as well. Last of all, another easy way to save a few dollars is be ready to book fast. If you stumble on a fantastic deal, don't hesitate — snap it up while you can.
Do you have any tips for my flight to Hillside?
Wherever you're coming from, flying can be a pleasurable experience if you're prepared. Check out these handy tips and tricks that will get your Hillside escape started on the right note. What to pack in your hand luggage:

  • The trick to having a great travel experience is to plan ahead. So, let's start with the essentials: passport, travel docs, credit cards and medications. Next, bring on board items that'll help pass the time, like some electronic devices or a magazine. You'll also want to bring your chargers, a comfy neck pillow and a pair of earphones. Last but not least, don't forget to toss in toiletries like a toothbrush, cleansing wipes and a fresh set of clothes.

Do not pack the following items in your hand luggage:

  • Check carefully that you don't have sharp objects (like a pocket knife) lurking in one of the zippers of your carry-on luggage. Other banned items include explosive or flammable products, such as fuel and matches, and gels and liquids in containers with a capacity of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Comfort should be your highest priority when choosing what to wear during your flight. Loose clothing is a smart option, as are flat, slip-on shoes.
  • Deep vein thrombosis (DVT) can pose a risk on long-haul flights. It results from blood clots forming due to poor circulation, so do some gentle foot and leg exercises in your seat and consider wearing compression tights or socks.

How to get through airport security fast when flying to Hillside?
As seasoned travellers know, the secret is to be well prepared before you get to the security gate. That way, you'll be stepping onto that plane to Hillside in a flash. Follow these helpful tips and get your trip off to a great start:

  • Be sure to have your ID and boarding pass easily accessible. They're the first things you'll be asked for by security.
  • Next up, both you and your hand luggage will be X-rayed. To speed things up, remove anything that is likely to trigger the alarm. Items such as your belt, coat and headphones need to go through the machine.
  • For just a few moments, you'll need to unplug from technology. Your phone, laptop and any other electronic gadgets must also go through the scanner.
  • Don't forget to remove liquids and gels from your carry-on luggage. They often need to be sent through the X-ray scanner separately. Each item should be 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 a few precious minutes. Boots are often required to be removed and separately scanned. Slip-on shoes usually aren't.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, put them in your checked luggage. They won't be allowed on board.

Book with confidence

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

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 Hillside 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 Hillside.

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

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $343

Trending flights to Hillside

Prices were available within the past 7 days and start at CA $203 for one-way flights and CA $344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Mon, Sep 14 - Thu, Sep 17
YTZ
Toronto
ORD
Chicago
CA $344 Roundtrip, just found
CA $344
Roundtrip
just found
Select Air Canada flight, departing Mon, Sep 14 from Toronto to Chicago, returning Thu, Sep 17, priced at CA $344 just found

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