Cheap Flights to Hillside , IL from CA $152

View CA $152 flight on Thu, Oct. 9, 2025Opens in a new window

Popular airlines to Hillside

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

How much is the cheapest flight to Hillside?

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
Tue, Sep. 23 - Fri, Sep. 26
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, just found
CA $243
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Sep. 23 from Toronto to Chicago, returning Fri, Sep. 26, priced at CA $243 just found
Air Canada
Sat, Sep. 13 - Sun, Sep. 14
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, just found
CA $243
Roundtrip
just found
Select Air Canada flight, departing Sat, Sep. 13 from Toronto to Chicago, returning Sun, Sep. 14, priced at CA $243 just found
United
Fri, Nov. 28 - Sun, Nov. 30
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, just found
CA $244
Roundtrip
just found
Select United flight, departing Fri, Nov. 28 from Toronto to Chicago, returning Sun, Nov. 30, priced at CA $244 just found
American Airlines
Fri, Sep. 12 - Sun, Sep. 28
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 15 hours ago
CA $256
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Fri, Sep. 12 from Calgary to Chicago, returning Sun, Sep. 28, priced at CA $256 found 15 hours ago
WestJet
Fri, Nov. 14 - Mon, Nov. 17
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 10 hours ago
CA $256
Roundtrip
found 10 hours ago
Select WestJet flight, departing Fri, Nov. 14 from Calgary to Chicago, returning Mon, Nov. 17, priced at CA $256 found 10 hours 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 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!

Frequently asked questions

What is the name of Hillside's airport?
Many visitors prefer to fly into O'Hare Intl. Airport (ORD) when visiting the buzzing city of Hillside.
How far is O'Hare Airport from central Hillside?
It's 11 kilometres from O'Hare Intl. Airport (ORD) to downtown Hillside. Make things easy by researching the fastest way of commuting from the airport to the city centre before you land.
What airport is best to fly into Hillside?
Before booking your flight to Hillside, it's a wise idea to decide which airport is most convenient. O'Hare Intl. Airport (ORD) is 11 kilometres from downtown. If you touchdown at Midway Airport, you'll be 16 kilometres away from the city centre.
How many airlines fly to Hillside?
There are 51 airlines that fly into Hillside from 237 worldwide airports.
Which airlines fly to Hillside?
United Airlines, American Airlines and Delta are the most frequent fliers to Hillside. The highest number of flights arrive here from New York, with United Airlines having the most services on this route.
How many nonstop flights are there to Hillside?
Flying to someplace new is much more fun when there aren't any annoying stopovers to slow you down. If you're jetting off to Hillside, the good news is that there are around 7,564 direct flights operating every week.
Where are the most popular flights to Hillside departing from?
The most popular flights to Hillside take off from New York, Washington and Dallas airports.
How long is the flight to Hillside Airport?
Where you depart from determines how long you'll be strapped into your seat. From New York to Hillside, the average flight time is 2 hours and 44 minutes. From Washington it's around 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Hillside?
We all know those lucky travellers who manage to nab wonderfully cheap fares wherever they go. Eager to know how to do it for your Hillside vacation? Don't leave it until the last moment to lock in your flight. Also, shop around and compare your options. If your destination has several airports, you may be able to pick up an excellent deal by flying into a less busy terminal. Lastly, be ready to book quickly if you stumble on a great price. It might not be available for too long. With a bit of know-how and a little good fortune, the perfect fare can be yours.
Do you have any tips for my flight to Hillside?
Wherever you're coming from, flying can be a pleasurable experience if you prepare well enough. We've put together a list of handy hints that will get your Hillside vacation started on the right foot. What to pack in your hand luggage:

  • First, pack your passport, travel docs, wallet and vital medications. Next, you'll want some entertainment to while away the hours. A thrilling book and a laptop filled with your favourite shows are some wonderful options. If you plan to catch a few z's, a neck pillow and a pair of noise-cancelling headphones will also come in handy. Finally, find room for a few toiletry items to ensure you arrive feeling fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Double-check that you don't have sharp objects (like a pocket knife) lurking in your hand luggage. Other restricted items include explosive or flammable goods, such as aerosol cans and fuel, and gels and liquids in containers with a capacity of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • The aisles of an aircraft are no place for a fashion parade. Layer up with comfortable clothing and pick shoes that are enclosed, flat and easy to pull on and off.
  • You're probably aware of deep vein thrombosis (DVT), a blood clotting condition caused by prolonged periods of inactivity. To reduce your risk on board, drink lots of water, consider wearing compression socks and move your legs and feet often.

How to get through airport security fast when flying to Hillside?
The answer is simple --- be organized. We've compiled some tips and tricks for a speedy trip through security. Watch out Hillside, here you come:

  • Have your passport and boarding pass within close reach. They'll be the first things you'll be asked to present to airport security.
  • Your belt, jacket, keys and other small items, like your headphones, will need to go through the X-ray machine. Make the whole process easier by removing them before your turn arrives.
  • All your electronics, including your tablet and phone, are also required to be separately scanned.
  • Remember to remove liquids and gels from your carry-on luggage. They usually need to be sent through the X-ray separately. Each product 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 several valuable minutes. Boots and heavy shoes are often required to be removed and separately scanned. Slip-on shoes usually aren't.
  • Airlines won't allow any sharp objects in your carry-on baggage. If you need to bring these kinds of items, pack them in your checked luggage.

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

Trending flights to Hillside

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
Tue, Sep. 23 - Fri, Sep. 26
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, just found
CA $243
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Sep. 23 from Toronto to Chicago, returning Fri, Sep. 26, priced at CA $243 just found
*Available to Expedia members.