Cheap Flights to Chicago , IL from CA $200

View CA $200 flight on Thu, Sep 24, 2026Opens in a new window

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How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at CA $200 for one-way flights and CA $339 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Jun 5 - Sat, Jun 6
YTZ
Toronto
ORD
Chicago
CA $341 Roundtrip, just found
CA $341
Roundtrip
just found
Select Air Canada flight, departing Fri, Jun 5 from Toronto to Chicago, returning Sat, Jun 6, priced at CA $341 just found
Porter Airlines
Fri, Jun 5 - Sat, Jun 6
YTZ
Toronto
MDW
Chicago
CA $341 Roundtrip, just found
CA $341
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Jun 5 from Toronto to Chicago, returning Sat, Jun 6, priced at CA $341 just found
United
Wed, Jun 3 - Wed, Jun 10
YYZ
Toronto
ORD
Chicago
CA $354 Roundtrip, just found
CA $354
Roundtrip
just found
Select United flight, departing Wed, Jun 3 from Toronto to Chicago, returning Wed, Jun 10, priced at CA $354 just found
Delta
Tue, Jul 21 - Mon, Aug 10
YYC
Calgary
ORD
Chicago
CA $365 Roundtrip, found 5 days ago
CA $365
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 21 from Calgary to Chicago, returning Mon, Aug 10, priced at CA $365 found 5 days ago
American Airlines
Sat, May 23 - Tue, May 26
YYC
Calgary
ORD
Chicago
CA $370 Roundtrip, just found
CA $370
Roundtrip
just found
Select American Airlines flight, departing Sat, May 23 from Calgary to Chicago, returning Tue, May 26, priced at CA $370 just found

Alternative airports near Half Day

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest option available. Flights from CA $392
MDW
Midway Intl.
Cheapest
Flights from CA $392

Frequently asked questions

What is the name of Chicago's airport?
Chicago has more than one airport, but most travellers touch down at O'Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Chicago?
The journey from O'Hare Intl. Airport (ORD) to downtown Chicago is fairly long. You'll need to travel 26 kilometres before you can check in to your city hotel.
What airport is best to fly into Chicago?
A flight to Chicago means hopping off the plane at O'Hare Airport or Chicago Airport. The first is 26 kilometres away from downtown. The second is 14 kilometres away.
How many airlines fly to Chicago?
There are a total of 51 airlines connecting Chicago with 237 airports globally.
Which airlines fly to Chicago?
Chicago receives the highest number of flights from United Airlines, American Airlines and Delta with United Airlines being the number one choice of airline. New York is the most popular city for passengers to jet off from.
How many nonstop flights are there to Chicago?
With roughly 7,564 nonstop flights running every week, you'll be hitting the runway in Chicago before you can ask, "Are we there yet?"
Where are the most popular flights to Chicago departing from?
The most popular flights to Chicago set off from New York, Washington and Dallas airports.
How long is the flight to Chicago Airport?
If it's New York you're leaving behind, you'll be in the air for around 2 hours and 44 minutes before you arrive in Chicago. Terminal to terminal from Washington generally takes 2 hours and 15 minutes and from Dallas, the average flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Chicago?
Don't leave booking your flight to Chicago until the last minute. That's one trick seasoned travellers use to get the best prices. Booking well in advance means more choices and cheaper flights. Don't stop there, however. Do some research and see if there is more than one airport at your destination. Fares often differ depending on which airport you go for. Don't forget to compare fares across air carriers too. Finally, another easy way to save a few dollars is be ready to book at a moment's notice. If you stumble on a good bargain, don't hold off — grab it while you can.
Do you have any tips for my flight to Chicago?
Depending on where you're coming from, your trip to Chicago could be simple and straightforward or it could go on forever. We've put together some handy tips that will help you start your next unforgettable escape on the right foot. What to pack in your hand luggage:

  • It's simple — first, pack your passport, travel documents, wallet and daily medications. Next, you'll need some in-flight entertainment to while away the hours. A thrilling book and a laptop filled with your favourite shows are some wonderful options. If you intend to take a quick nap, a neck pillow and a pair of earplugs will also be useful. Finally, leave some space for a few toiletry items to ensure you touchdown feeling fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of shampoo and hair gel in your checked luggage. Any gels or liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp or pointed objects, like a Swiss Army knife, and dangerous products which are explosive or flammable, such as spray paint, flares and fireworks, are also restricted.

What to wear on a flight:

  • Choose comfort over style. Prepare for changes in temperature by donning layers, and opt for flat, enclosed shoes like sneakers.
  • Most of us have heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To reduce your risk on board, stay hydrated, consider wearing compression socks and move your lower limbs often.

How to get through airport security fast when flying to Chicago?
The secret is to be well prepared before you arrive at airport security. That way, you'll be boarding that plane to Chicago in a flash. Follow these helpful tips and get your vacation off to a fantastic start:

  • First things first. Your passport and boarding pass will need to be shown to airport security personnel. Keep them at hand so you don't have to dig around for them.
  • Your belt, jacket, keys and other small items, like your headphones, will need to go through the X-ray machine. Make the whole process faster by removing them as your turn draws near.
  • For just a few moments, you'll need to unplug from the digital world. Your phone, laptop and any other electronic gadgets will need to go through the scanner.
  • Remove all gels and liquids from your hand luggage. They often need to be sent through the X-ray machine separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a single quart-size (one litre), clear zip-close bag.
  • The right choice of footwear can save you several minutes. Boots are often required to be removed and X-rayed separately. Slip-on shoes usually aren't.
  • Airlines will not allow any sharp objects to come on board with you. If you must bring these kinds of items, check them in.

Book with confidence

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

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 Chicago 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 Chicago.

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

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $240

Trending flights to Chicago

Prices were available within the past 7 days and start at CA $200 for one-way flights and CA $339 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Sep 10 - Thu, Sep 10
YTZ
Toronto
ORD
Chicago
CA $339 Roundtrip, found 3 days ago
CA $339
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu, Sep 10 from Toronto to Chicago, returning Thu, Sep 10, priced at CA $339 found 3 days ago

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