CHI - YYZ

$75 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 9/30. 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

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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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

Tue, Sep 30 - Thu, Oct 2
Air Canada Logo
9:55 am - 12:37 pmORD-YYZ
1h 42mnonstop
Air Canada Logo
8:15 am - 9:09 amYYZ-ORD
1h 54mnonstop
$189Air Canada
Find Deal
Tue, Sep 30 - Thu, Oct 2
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
Air Canada Logo
6:15 am - 9:51 amYYZ-ORD
4h 36m1 stop
$193Air Canada
Find Deal
Mon, Oct 20 - Thu, Oct 23
 Logo
7:43 pm - 2:05 pmORD-YYZ
17h 22m1 stop
 Logo
6:30 am - 4:04 pmYYZ-ORD
10h 34m1 stop
Fri, Sep 26 - Tue, Sep 30
 Logo
6:44 pm - 2:05 pmORD-YYZ
18h 21m1 stop
 Logo
6:30 am - 5:39 pmYYZ-ORD
12h 09m1 stop
Thu, Oct 2 - Sun, Oct 5
United Airlines Logo
12:52 pm - 3:46 pmORD-YYZ
1h 54mnonstop
United Airlines Logo
7:00 am - 7:58 amYYZ-ORD
1h 58mnonstop
$201United Airlines
Find Deal
Wed, Oct 1 - Thu, Oct 2
United Airlines Logo
9:20 pm - 10:04 amORD-YYZ
11h 44m1 stop
United Airlines Logo
1:00 pm - 2:01 pmYYZ-ORD
2h 01mnonstop
$205United Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
Delta Logo
12:15 pm - 6:35 pmYYZ-MDW
7h 20m1 stop
$244Delta
Find Deal
Fri, Oct 3 - Mon, Oct 6
Delta Logo
6:15 pm - 10:56 pmMDW-YYZ
3h 41m1 stop
Delta Logo
12:15 pm - 6:25 pmYYZ-MDW
7h 10m1 stop
$277Delta
Find Deal
Sat, Oct 18 - Sun, Oct 19
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
$286WestJet
Find Deal
Wed, Nov 19 - Sun, Nov 23
WestJet Logo
10:47 am - 9:59 pmMDW-YYZ
10h 12m1 stop
WestJet Logo
12:25 pm - 9:52 amYYZ-MDW
22h 27m1 stop
$294WestJet
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers 6 inches more legroom.
Use the UP Express train from YYZ for a quick downtown trip.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Air Canada
Cheapest • from $189 (round-trip)
Porter Airlines
Best reviews • 7.9 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 travelers who book at least 5 weeks in advance save around 51% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 18% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$189
Overall average: $242
Air Canada
Tue 9/30Thu 10/2
ORD - YYZ • Non-stop
Cheapest one-way
$75
Typical prices: $138-278
Air Canada
Tue 9/30
ORD - YYZ • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pearson Intl!
Expert advice

Expert advice for your flight from Chicago to Pearson Intl

 
Snippets provided in this section are AI-generated based on a summarization 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
Air Canada

Air Canada's Preferred Economy seats offer 4 extra inches of legroom for added comfort.


Air Canada provides free messaging for Aeroplan members on flights with Wi-Fi.

Read more about Air Canadaby Stefanie Waldek
United Airlines

United offers Priority Boarding to avoid gate-checking carry-ons, ideal for quick boarding.


United's Economy Plus offers up to 6 inches more legroom, enhancing comfort on short flights.

American Airlines

American's Main Cabin Extra offers early boarding and complimentary drinks, enhancing travel comfort.


American Airlines' Wi-Fi offers 20 minutes free with an ad, useful for quick tasks.

Airports
ORD

For a quick commute to downtown Chicago, take the CTA Blue Line from ORD. It's reliable and avoids traffic delays.

Read more about ORDby Stefanie Waldek
YYZ

Use the UP Express train from YYZ to reach downtown Toronto in just 25 minutes, avoiding traffic congestion.

Read more about YYZby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada, United Airlines, ORD and YYZ

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
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
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.

How much is a round-trip flight from Chicago to Toronto Pearson Intl Airport?

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 $172 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.

If your flying dates are flexible, you should consider flying to Toronto Pearson Airport on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Toronto Pearson Airport. For your return ticket, we recommend flying on a Saturday and avoiding Mondays for the best deals.

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 $241 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $341 and $335 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.

No, with an average price for the route of $313, prices are generally cheapest when you fly direct.

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 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$75
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 4% increase in price.
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 $75 for a one-way ticket and $189 for a round-trip.

  • Do I need a passport to fly between Chicago and Toronto Pearson Airport?

    Yes, you’ll need a passport to travel to Toronto Pearson Airport from Chicago.

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

    Chicago is served by 2 major airports and there is only 1 main airport in Toronto Pearson Airport. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Toronto Pearson Intl.

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

    American Airlines, Air Canada, United Airlines, and Finnair offer inflight Wi-Fi service on the Chicago to Toronto Pearson Airport flight route.

  • 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 nonstop flights from Chicago to Toronto Pearson Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Toronto are Porter Airlines and United Airlines. With an average price for the route of $159 and an overall rating of 7.9, Porter Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $342 and an overall rating of 7.4.

  • 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 travelers 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 $212 or less one-way and $270 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 direct 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 direct flights

Reviews of the top 4 airlines serving 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.
7.9
Porter AirlinesOverall score based on 363 reviews
7.9Comfort
8.1Boarding
7.6Food
8.6Crew
7.0Entertainment
Airline reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

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.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Flight was actually on Air Canada. The flight itself was fine. Nothing special. Food was pretty pathetic except for cookies. They offered plenty of food and drinks but just wasn't very good. Even for airline food.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

Was a normal flight but it was delayed, and there wasn't an explanation.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

I found the boarding easy and my seat was very comfortable as I had a lot of leg room. I am not too happy that I no longer have lounge access even though I used to get it with my TD credit card.

Flight cancelled. Major disruption to our travel. Do not use Air Canada from KC. To few flights.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Re luggage I carried a backpack only. I did not check any bags in. However there were other passengers with carry on luggage going in the plane. My question is why are others allowed to have a carry on luggage inside the plane? Shouldn’t they have dropped it off at the gate? I’m asking because I could have brought the same thing instead of a backpack only. Please clarify for future reference. Thank you.

Like the service. Very hard to communicate or contact when have problems

Check in staff was incredibly rude and condescending. When I arrived at the gate I had been charged $125 for a checked back. I did have or check a bag. When I brought this to the attention of the staff member who checked me in, she said that she made a mistake and there was nothing she could do about it. I asked her to remove the charge and refund credit card, she said she could not and that I had to call my credit card company to contest the charge. I called Air Canada customer support, was put on hold, after 43 minutes a received a messages stating customer service was overwhelmed with calls and was then hung up on.

Refreshments and Air Hostess was good. Issues with customs in Toronto caused flight to depart and left me behind twice. Vouchers for delayed flight needs to increase.

Long wait to check in at the priority counter in Toronto

I had no communication, receipt etc from Air Canada until hours before flight

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

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