CHI - YYZ

C$ 120 Find Cheap Flights from Chicago to Toronto Pearson Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Pearson Intl departing on 3/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Toronto Pearson Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 274
Overall average: C$ 516
American Airlines
Fri 20/2Mon 23/2
ORD - YYZ • 1 stop
Cheapest direct flights
C$ 277
Typical prices: C$ 413-C$ 619
Air Canada
Thu 11/12Sun 14/12
ORD - YYZ • Direct
Our travellers' advice
AI-generated summary based on content written by travel experts
American's Basic Economy has late boarding and no free bags.
Use the Union Pearson Express for a quick ride to Toronto.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from C$ 274 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-YYZ
Cheapest
ORD-YYZ
Most popular
Insights
Insights
Insights
Insights
When to book
5 weeks
in advance
Our data shows that travellers who book at least 5 weeks in advance save around 55% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 18% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Pearson Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Pearson Intl (CHI-YYZ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Pearson Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Pearson Intl

Fri, 20 Feb - Mon, 23 Feb
American Airlines Logo
6:00 a.m. - 11:50 a.m.ORD-YYZ
4h 50m1 stop
American Airlines Logo
6:29 p.m. - 7:29 p.m.YYZ-ORD
2h 00mdirect
C$ 274American Airlines
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Air Canada Logo
3:55 p.m. - 6:34 p.m.ORD-YYZ
1h 39mdirect
Air Canada Logo
6:30 p.m. - 7:30 p.m.YYZ-ORD
2h 00mdirect
C$ 277Air Canada
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Air Canada Logo
3:55 p.m. - 6:34 p.m.ORD-YYZ
1h 39mdirect
Air Canada Logo
6:20 a.m. - 11:18 a.m.YYZ-ORD
5h 58m1 stop
C$ 281Air Canada
Find Deal
Fri, 5 Dec - Fri, 12 Dec
American Airlines Logo
8:10 a.m. - 10:56 a.m.ORD-YYZ
1h 46mdirect
American Airlines Logo
4:30 p.m. - 11:39 p.m.YYZ-ORD
8h 09m1 stop
C$ 282American Airlines
Find Deal
Sat, 7 Mar - Sun, 8 Mar
United Airlines Logo
6:40 p.m. - 9:28 p.m.ORD-YYZ
1h 48mdirect
United Airlines Logo
9:00 a.m. - 10:09 a.m.YYZ-ORD
2h 09mdirect
C$ 292United Airlines
Find Deal
Fri, 27 Feb - Wed, 11 Mar
United Airlines Logo
6:00 a.m. - 1:43 p.m.ORD-YYZ
6h 43m1 stop
United Airlines Logo
9:00 p.m. - 9:59 p.m.YYZ-ORD
1h 59mdirect
C$ 310United Airlines
Find Deal
Sun, 14 Dec - Fri, 2 Jan
Delta Logo
6:45 a.m. - 2:48 p.m.ORD-YYZ
7h 03m1 stop
Delta Logo
9:54 a.m. - 5:22 p.m.YYZ-ORD
8h 28m1 stop
C$ 329Delta
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Delta Logo
9:34 a.m. - 5:15 p.m.MDW-YYZ
6h 41m1 stop
Delta Logo
6:05 a.m. - 8:54 a.m.YYZ-MDW
3h 49m1 stop
C$ 329Delta
Find Deal
Tue, 20 Jan - Thu, 22 Jan
WestJet Logo
1:49 p.m. - 11:13 p.m.MDW-YYZ
8h 24m1 stop
WestJet Logo
6:14 p.m. - 9:58 a.m.YYZ-MDW
16h 44m1 stop
C$ 425WestJet
Find Deal
Fri, 16 Jan - Mon, 19 Jan
WestJet Logo
7:16 p.m. - 3:53 p.m.MDW-YYZ
19h 37m2 stops
WestJet Logo
6:10 a.m. - 5:32 p.m.YYZ-MDW
12h 22m1 stop
C$ 433WestJet
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Pearson Intl flights

Get data-powered insights and trends into flights from Chicago to Pearson Intl to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Toronto Pearson Intl Airport flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Toronto Pearson Intl Airport costs C$ 239 on the route between Chicago O'Hare Intl Airport (ORD) and Toronto Pearson Intl Airport (YYZ). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Toronto Pearson Airport?

The average price of all round-trip flights from Chicago to Toronto Pearson Intl Airport clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Toronto Pearson Airport, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

What is the cheapest month to fly from Chicago to Toronto Pearson Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Toronto Pearson Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Toronto Pearson Intl Airport is June, where tickets cost C$ 340 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is C$ 481 and C$ 473 respectively.

Can I save money by flying with a layover from Chicago to Toronto Pearson Intl Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 290 on average.

How far in advance should I book a flight from Chicago to Toronto Pearson Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Toronto Pearson Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Toronto Pearson Intl Airport, you should book around 5 weeks before departure, which saves you about 55% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Pearson Intl

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Main Cabin Extra offers early boarding and complimentary drinks for a fee.


Basic Economy includes late boarding and no free checked bags.

Air Canada

Priority check-in available for higher fare classes and elite status members.


Economy seats offer 76-86 cm legroom; Preferred Economy adds 10 cm for a fee.

Read more about Air Canadaby Stefanie Waldek
Airports
ORD

For a quick trip to downtown Chicago, take the CTA Blue Line from ORD, which runs 24/7 and takes about 45 minutes.

Read more about ORDby Stefanie Waldek
YYZ

Use the Union Pearson Express for a stress-free 25-minute ride from YYZ to downtown Toronto, with trains every 15 minutes.

Read more about YYZby Mark Stachiew
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Mark Stachiew

Mark Stachiew

Expert on YYZ

Mark Stachiew

Mark Stachiew

Mark Stachiew has been exploring the world and writing about it for more than 30 years. His travel stories have appeared in numerous newspapers, magazines and online publications in Canada, the United States and beyond.

Read more

Good to know

Low seasonJanuary
Cheapest flightC$ 120
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly (16% more expensive on average)
Flight from Chicago O'Hare Airport to Toronto Pearson Airport

When to book flights from Chicago to Pearson Intl

Are your dates flexible? Find out the best times to travel from Chicago to Pearson Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Toronto Pearson Airport flights

  • What is the cheapest flight from Chicago to Toronto Pearson Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago to Toronto Pearson Intl Airport was C$ 120 for a one-way ticket and C$ 274 for a round-trip.

  • Which airports will I be using when flying from Chicago to Toronto Pearson Airport?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Toronto Pearson Airport (Toronto Pearson Intl). The cheapest flights are generally found on the Chicago O'Hare Airport to Toronto Pearson Intl flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Toronto Pearson Airport?

    All the following airlines offer inflight Wi-Fi service on the Chicago to Toronto Pearson Airport flight route: Air Canada, American Airlines, United Airlines, British Airways, Finnair, Iberia, and Porter Airlines.

  • Which aircraft models fly most regularly from Chicago to Toronto Pearson Airport?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Toronto Pearson Airport flight route.

  • Which airline alliances offer flights from Chicago to Toronto Pearson Airport?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Toronto Pearson Airport, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Toronto Pearson Airport?

    There are direct flights from Chicago to Toronto Pearson Airport on a daily basis.

  • Which is the best airline for flights from Chicago to Toronto, United Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Chicago to Toronto are United Airlines and Air Canada. With an average price for the route of C$ 463 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of C$ 372 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Toronto Pearson Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Toronto Pearson Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Toronto Pearson Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto Pearson Airport from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Toronto Pearson Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Toronto Pearson Airport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Toronto Pearson Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Toronto Pearson Airport from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Toronto Pearson Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 130 or less one-way and C$ 353 or less round-trip.

Prefer to fly direct from Chicago to Toronto Pearson Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Toronto Pearson Intl.
Find which airlines fly direct from Chicago to Toronto Pearson Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to Toronto Pearson Intl

Monday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Tuesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Wednesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Thursday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Friday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Saturday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Sunday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

See more nonstop flights

Direct returns

Toronto Pearson Intl to Chicago

Monday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Tuesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Wednesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Thursday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Friday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Saturday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Sunday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

See more nonstop flights

Reviews of the top airlines flying from Chicago to Pearson Intl

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Toronto. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Pearson Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9007 reviews
7.1Entertainment
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

10.0 ExcellentDr. Joseph, Oct 2025ORD - STL
Read more United Airlines reviews

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

Elderly female flight attendant was not customer friendly. There were only about 12 people on a regional jet that had about 60 seats. There were 8 exit row seats and none of them were taken. We attempted to sit in those seats and the flight attendant gave the standard " you didn't pay for those" so she would not allow us to move. What harm would that have caused ? They assigned seats to 5 of the 12 people in 2 rows, row 20 and 21. A simple friendly customer experience gesture of allowing us to sit in exit rows would have gone a long way in me having a very favorable impression on Air Canada. After that I have very poor impression of Air Canada and will not fly with them when I can avoid it.

Pearson Airport could not properly handle all the passengers who they needed to process in order to properly get them on board. As a result, I missed the departure of my flight from Toronto. The only saving grace is that Air Canada found a flight that only delayed me by one hour. However, this was no thanks to Pearson Airport!

Almost everything it was a “cool” ambiance but we arrived to Toronto so that it’s ok for me

The crew was really nice. The plane seats were kinda small even for a 5’6” / 158 lbs person.

Check in agent was very helpful and polite. He helped me board the earlier flight back home instead of waiting 2 hours at the airport for the next flight

Everything you need to know for your flight from Chicago to Pearson Intl

Information on your arrival and departure airports