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Cheap Flights to Chicago , IL from CA $191

View CA $191 flight on Thu, Sep 10, 2026Opens in a new window

Popular airlines to Chicago

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How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at CA $191 for one-way flights and CA $320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Porter Airlines
United
American Airlines
Delta

Alternative airports near Chicago

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

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

From CA $190 - CA $555 per traveller.

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

Find Your Flights to Chicago CHI

Cheap flights to Chicago (CHI)

Get started finding a cheap flight to Chicago on Expedia by either choosing a deal on this page or using the search bar to enter your travel dates, origin airport, and whether you want a roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Chicago.

Roundtrip prices range from CA $320 - CA $341, and one-ways Chicago start as low as CA $191.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

Airlines that fly to Chicago (CHI)

You have several options for which airline you choose to travel with to Chicago. There are 10 airlines flying into CHI: Porter Airlines, Air Canada, American Airlines, United, Air Transat, Delta. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check a bag or bring a carry-on, check whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked/carry-on baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programmes may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel on one online platform.

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at optimal times. Airfare to Chicago (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to CHI in September and in September for one-ways.

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24 hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Find Your Flights to Chicago CHI

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $224

Trending flights to Chicago

Prices were available within the past 7 days and start at CA $191 for one-way flights and CA $320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada

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