Cheap Flights to Chicago , IL from CA $152

View CA $152 flight on Wed, Oct. 15, 2025Opens 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 $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
Sat, Nov. 15 - Mon, Nov. 17
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, found 1 hour ago
CA $243
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Nov. 15 from Toronto to Chicago, returning Mon, Nov. 17, priced at CA $243 found 1 hour ago
Porter Airlines
Fri, Nov. 21 - Sun, Nov. 23
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, just found
CA $243
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Nov. 21 from Toronto to Chicago, returning Sun, Nov. 23, priced at CA $243 just found
United
Thu, Nov. 6 - Sun, Nov. 9
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, just found
CA $244
Roundtrip
just found
Select United flight, departing Thu, Nov. 6 from Toronto to Chicago, returning Sun, Nov. 9, priced at CA $244 just found
American Airlines
Fri, Sep. 19 - Sun, Sep. 21
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, just found
CA $261
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep. 19 from Toronto to Chicago, returning Sun, Sep. 21, priced at CA $261 just found
Air Transat
Fri, Sep. 5 - Sat, Sep. 13
YTZ
Toronto
MDW
Chicago
CA $285 Roundtrip, found 3 days ago
CA $285
Roundtrip
found 3 days ago
Select Air Transat flight, departing Fri, Sep. 5 from Toronto to Chicago, returning Sat, Sep. 13, priced at CA $285 found 3 days ago

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

August is typically the cheapest month to fly

From CA $120 - CA $603 per traveller.

Graph displaying average flight prices per month

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!

Frequently asked questions

What is the name of Chicago's airport?
Chicago has multiple airports, but most visitors use O'Hare Intl. Airport (ORD).
How far is O'Hare Airport from central Chicago?
ORD is 26 kilometres from downtown Chicago, so expect a decent commute into the city.
What airport is best to fly into Chicago?
With a number of airports to pick from, Chicago is easy to book a flight to at the last moment. The terminals that see the majority of the city's air travel are O'Hare Airport (26 kilometres from downtown), MDW (14 kilometres from downtown) and Waukegan Regional Airport (UGN) (64 kilometres from downtown).
How many airlines fly to Chicago?
There are 51 air carriers connecting Chicago with 237 airports across the world.
Which airlines fly to Chicago?
Chicago receives the most flights from United Airlines, American Airlines and Delta with United Airlines being the favourite choice of airline. New York is the most popular city for travellers to jet off from.
How many nonstop flights are there to Chicago?
Flying to somewhere new is much more straightforward when there aren't any stopovers to worry about. If you're making your way to Chicago, the fantastic news is that there are roughly 7,564 direct flights every week.
Where are the most popular flights to Chicago departing from?
Flights to Chicago from New York, Washington and Dallas airports are always popular.
How long is the flight to Chicago Airport?
If you're flying to Chicago from New York, you'll have a flight time of 2 hours and 44 minutes. Those leaving from Washington can expect to be travelling for 2 hours and 15 minutes. From Dallas it's approximately 2 hours and 18 minutes away.
How to book the cheapest flight to Chicago?
Don't leave locking in your flight to Chicago until the last possible moment. That's one trick frequent jet-setters use to get the best deals. Booking ahead means more choices and cheaper flights. Another fantastic way to get the most affordable fare is to shop around. If where you're headed has multiple airports, don't forget to look into the cost of flying into a less busy terminal. And finally, don't forget that it's first in, best dressed. Familiarize yourself with airfare costs and be ready to snap up a ticket as soon as you spot a bargain. The sweetest deals don't last long.
Do you have any tips for my flight to Chicago?
We've got the lowdown on how to make your flight as stress-free as possible. Follow our tips and tricks and you'll be hightailing it through the airport and exploring Chicago before you know it. What to pack in your hand luggage:

  • Air travel can be easy if you've got all the right things. Firstly, you'll need basic toiletry items, such as lip balm and hand cream, a spare set of clothes and a magazine or two. Next, find room in your carry-on bag for your electronic gadgets, chargers, your medications and maybe a proper neck pillow as well. Lastly, and most importantly, be sure to take your passport, travel documents and some money.

Do not pack the following items in your hand luggage:

  • Check carefully that you don't have a sharp object lurking in the bottom of your carry-on luggage. Other prohibited items include flammable or explosive goods, such as bleach 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:

  • Go for comfort over style. Prepare for temperature changes in the cabin by donning layers, and pick closed-toe, flat shoes like sneakers.
  • The result of prolonged periods of inactivity, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers during long-haul flights. Lower your risks by staying hydrated, keeping your ankles and legs moving and wearing compression tights or socks.

How to get through airport security fast when flying to Chicago?
A little pre-planning before your flight can make your getaway to Chicago a pleasure. Here are some useful tips and tricks for a swift journey through security:

  • First things first. Your passport and boarding pass will need to be presented to airport security personnel. Have them close by so you don't hold up the line.
  • Next up, both you and your hand luggage will be X-rayed. To make the process quick and painless, take off anything that might set the alarms off. Personal belongings like your belt, jacket and headphones will be required to go through the machine.
  • For just a few moments, you'll have to unplug from the digital world. Your phone, tablet and any other electronics must also go through the scanner.
  • Want to bring along your favourite cologne? No problem. As long as it's in a container no larger than 3.4 ounces (100 millilitres) and it's stored in a clear zip-close bag, it's fine to bring with you in your carry-on baggage.
  • There's a chance you'll be required to take your shoes off for scanning, so wearing slip-on sneakers is always a wise idea.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp objects like a pocket knife or tools, put them in your checked suitcase. They won't be allowed on board and will be confiscated.

Flights to Chicago information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $92

Trending flights to Chicago

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
Sat, Nov. 15 - Mon, Nov. 17
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, found 1 hour ago
CA $243
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Nov. 15 from Toronto to Chicago, returning Mon, Nov. 17, priced at CA $243 found 1 hour ago
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