CHI - YYZ

$83 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 1/28. 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$185
Overall average: $337
Air Canada
Thu 1/29Sun 2/1
ORD - YYZ • Non-stop
Cheapest one-way
$83
Typical prices: $148-$333
Multiple Airlines
Wed 1/28
ORD - YYZ • 1 stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
United Airlines
Cheapest • from $220 (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 travelers who book at least 5 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 16% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
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

Thu, Jan 29 - Sun, Feb 1
Air Canada Logo
8:00 am - 10:40 am
ORD
-
YYZ
1h 40mnonstop
Air Canada Logo
12:05 pm - 1:01 pm
YYZ
-
ORD
1h 56mnonstop
$185Air Canada
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
8:43 pm - 2:40 pm
ORD
-
YYZ
16h 57m1 stop
Multiple Airlines Logo
12:15 pm - 7:38 pm
YYZ
-
ORD
32h 23m3 stops
$187Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
8:43 pm - 2:40 pm
ORD
-
YYZ
16h 57m1 stop
Multiple Airlines Logo
12:15 pm - 7:38 pm
YYZ
-
ORD
32h 23m3 stops
$189Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Air Canada Logo
8:00 am - 10:40 am
ORD
-
YYZ
1h 40mnonstop
Air Canada Logo
6:45 pm - 7:45 pm
YYZ
-
ORD
2h 00mnonstop
$194Air Canada
Fri, Feb 6 - Tue, Feb 10
American Airlines Logo
8:09 am - 3:30 pm
ORD
-
YYZ
6h 21m1 stop
American Airlines Logo
11:30 am - 12:25 pm
YYZ
-
ORD
1h 55mnonstop
$195American Airlines
Thu, Feb 12 - Tue, Feb 17
American Airlines Logo
8:14 am - 10:56 am
ORD
-
YYZ
1h 42mnonstop
American Airlines Logo
5:15 pm - 9:19 pm
YYZ
-
ORD
5h 04m1 stop
$200American Airlines
Mon, Feb 2 - Fri, Feb 6
Delta Logo
6:35 pm - 10:42 pm
MDW
-
YYZ
3h 07m1 stop
Delta Logo
10:05 am - 5:55 pm
YYZ
-
MDW
8h 50m1 stop
$233Delta
Thu, Feb 19 - Tue, Feb 24
Delta Logo
9:50 am - 3:59 pm
MDW
-
YYZ
5h 09m1 stop
Delta Logo
6:30 am - 1:07 pm
YYZ
-
MDW
7h 37m1 stop
$234Delta
Wed, Jan 14 - Fri, Jan 23
WestJet Logo
1:28 pm - 7:13 pm
MDW
-
YYZ
4h 45m1 stop
WestJet Logo
6:00 am - 8:52 am
YYZ
-
MDW
3h 52m1 stop
$302WestJet
Wed, Mar 25 - Mon, Mar 30
WestJet Logo
6:35 pm - 10:38 pm
MDW
-
YYZ
3h 03m1 stop
WestJet Logo
10:05 am - 12:29 pm
YYZ
-
MDW
3h 24m1 stop
$303WestJet
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 $180 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 Friday 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 February and January, where the average cost of round-trip tickets is $335 and $332 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 $232 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 54% 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

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

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.

YYZ

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

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

Good to know

Low seasonJanuary
Cheapest flight$83
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 13% lower 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 $83 for a one-way ticket and $184 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?

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

    The two airlines most popular with KAYAK users for flights from Chicago to Toronto are United Airlines and American Airlines. With an average price for the route of $328 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $349 and an overall rating of 7.2.

  • 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 $169 or less one-way and $410 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 3 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.
7.4
United AirlinesOverall score based on 9095 reviews
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

8.0 ExcellentSteve, Dec 2025
DEN - YYZ
Read more United Airlines reviews

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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.

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

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.

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

Information on your arrival and departure airports