CHI - YYZ

C$ 104 Find Cheap Flights from Chicago to Toronto

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 23/10. 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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Booking Insights
Flight Deals

Cheap Flights from Chicago to Toronto (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 Toronto 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, 23 Oct - Mon, 27 Oct
Multiple Airlines Logo
7:43 p.m. - 2:05 p.m.ORD-YYZ
17h 22m1 stop
Multiple Airlines Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
C$ 275Multiple Airlines
Find Deal
Thu, 23 Oct - Mon, 27 Oct
Multiple Airlines Logo
12:53 p.m. - 9:07 p.m.ORD-YYZ
7h 14m1 stop
Multiple Airlines Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
C$ 283Multiple Airlines
Find Deal
Wed, 22 Oct - Sun, 26 Oct
Multiple Airlines Logo
7:43 p.m. - 2:05 p.m.ORD-YYZ
17h 22m1 stop
Multiple Airlines Logo
4:00 p.m. - 3:49 p.m.YYZ-ORD
24h 49m1 stop
C$ 286Multiple Airlines
Find Deal
Tue, 7 Oct - Mon, 13 Oct
Multiple Airlines Logo
5:05 a.m. - 2:05 p.m.ORD-YYZ
8h 00m1 stop
Multiple Airlines Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
C$ 293Multiple Airlines
Find Deal
Fri, 31 Oct - Mon, 3 Nov
Multiple Airlines Logo
5:25 a.m. - 8:00 p.m.ORD-YYZ
13h 35m1 stop
Multiple Airlines Logo
4:00 p.m. - 10:39 p.m.YYZ-ORD
7h 39m1 stop
C$ 298Multiple Airlines
Find Deal
Fri, 31 Oct - Sun, 9 Nov
Multiple Airlines Logo
5:25 a.m. - 8:00 p.m.ORD-YYZ
13h 35m1 stop
Multiple Airlines Logo
4:00 p.m. - 10:42 a.m.YYZ-ORD
19h 42m1 stop
C$ 300Multiple Airlines
Find Deal
Mon, 6 Oct - Mon, 13 Oct
Multiple Airlines Logo
7:43 p.m. - 2:05 p.m.ORD-YYZ
17h 22m1 stop
Multiple Airlines Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
C$ 301Multiple Airlines
Find Deal
Sat, 1 Nov - Mon, 3 Nov
Multiple Airlines Logo
6:00 a.m. - 2:20 p.m.ORD-YYZ
7h 20m1 stop
Multiple Airlines Logo
4:00 p.m. - 10:39 p.m.YYZ-ORD
7h 39m1 stop
C$ 304Multiple Airlines
Find Deal
Sat, 4 Oct - Sat, 18 Oct
WestJet Logo
1:40 p.m. - 12:31 a.m.ORD-YYZ
9h 51m1 stop
WestJet Logo
8:00 a.m. - 4:43 p.m.YYZ-ORD
9h 43m1 stop
C$ 344WestJet
Find Deal
Sat, 4 Oct - Thu, 16 Oct
WestJet Logo
1:40 p.m. - 12:31 a.m.ORD-YYZ
9h 51m1 stop
WestJet Logo
8:00 a.m. - 4:43 p.m.YYZ-ORD
9h 43m1 stop
C$ 345WestJet
Find Deal

Everything you should know

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 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 51% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 19% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 275
Overall average: C$ 403
Multiple Airlines
Thu 23/10Mon 27/10
ORD - YYZ • 1 stop
Cheapest direct flights
C$ 403
Typical prices: C$ 247-507
Air Canada
Thu 23/10Mon 27/10
ORD - YYZ • Direct
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KAYAK searches hundreds 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 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
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$ 113 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?

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, you should consider leaving on a Saturday 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 Tuesdays.

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$ 333 (return) on average. On the other hand, the most expensive months are September and December, where the average cost of round-trip tickets is C$ 471 and C$ 471 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$ 127 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 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 flightC$ 104
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly (14% 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 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$ 75 for a one-way ticket and C$ 199 for a round-trip.

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

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Toronto (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?

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

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

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

  • Which airline alliances offer flights from Chicago to Toronto?

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

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

    There are direct flights from Chicago to Toronto 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$ 454 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$ 392 and an overall rating of 7.1.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto 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?

    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 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?

    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 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$ 354 or less one-way and C$ 314 or less round-trip.

Prefer to fly direct from Chicago to Toronto?

 
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 8929 reviews
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

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.

10.0 ExcellentAnonymous, Aug 2025EWR - YYZ
Read more United Airlines reviews

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.

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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