CHI - YYZ

C$ 150 Find Cheap Flights from Chicago to Toronto – Compare and Save

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 11/9. 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

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Everything you should know

Cheapest round-trip
C$ 335
Typical prices: C$ 314-C$ 498
Air Canada
Sun 13/9Wed 16/9
ORD - YYZ • Direct
Cheapest one-way flights
C$ 150
Typical prices: C$ 153-C$ 378
Air Canada
Fri 11/9
ORD - YYZ • 1 stop
Advice from real travellers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy has late boarding and no free checked bags.
Air Canada Preferred Economy adds 10 cm legroom; higher fares get priority check-in.
Expert advice
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Top airlines
Cheapest • from C$ 335 (round-trip)
Best reviews • 7.4 score
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Direct flights
You can fly direct with Air Canada, American Airlines, and United Airlines. Average duration is 1h 49m
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Top routes
Cheapest
Most popular
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Avoid delays
Most punctual • 83% on-time
Best time • Fewest delays
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When to book
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 49% compared to booking last minute.
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When to travel
Cheapest • 39% price drop
Most popular
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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

Sun, 13 Sep - Wed, 16 Sep
Air Canada Logo
2:15 p.m. - 5:01 p.m.
ORD
-
YYZ
1h 46mdirect
Air Canada Logo
2:00 p.m. - 2:55 p.m.
YYZ
-
ORD
1h 55mdirect
C$ 335Air Canada
Sun, 16 Aug - Sun, 23 Aug
Air Canada Logo
9:50 a.m. - 12:35 p.m.
ORD
-
YYZ
1h 45mdirect
Air Canada Logo
8:05 a.m. - 9:00 a.m.
YYZ
-
ORD
1h 55mdirect
C$ 342Air Canada
Sat, 1 Aug - Thu, 6 Aug
Air Canada Logo
3:45 p.m. - 6:30 p.m.
ORD
-
YYZ
1h 45mdirect
Air Canada Logo
6:55 p.m. - 7:52 p.m.
YYZ
-
ORD
1h 57mdirect
C$ 351Air Canada
Tue, 18 Aug - Wed, 26 Aug
Air Canada Logo
8:40 p.m. - 11:25 p.m.
ORD
-
YYZ
1h 45mdirect
Air Canada Logo
6:55 p.m. - 7:52 p.m.
YYZ
-
ORD
1h 57mdirect
C$ 352Air Canada
Thu, 30 Jul - Mon, 3 Aug
Air Canada Logo
2:15 p.m. - 5:01 p.m.
ORD
-
YYZ
1h 46mdirect
Air Canada Logo
6:55 p.m. - 7:52 p.m.
YYZ
-
ORD
1h 57mdirect
C$ 353Air Canada
Sun, 16 Aug - Sun, 23 Aug
Air Canada Logo
8:40 p.m. - 11:25 p.m.
ORD
-
YYZ
1h 45mdirect
Air Canada Logo
8:05 a.m. - 9:00 a.m.
YYZ
-
ORD
1h 55mdirect
C$ 355Air Canada
Wed, 7 Oct - Thu, 15 Oct
Delta Logo
9:29 a.m. - 5:20 p.m.
MDW
-
YYZ
6h 51m
1 stop
Delta Logo
12:10 p.m. - 6:05 p.m.
YYZ
-
MDW
6h 55m
1 stop
C$ 423Delta
Fri, 4 Sep - Mon, 7 Sep
Delta Logo
1:25 p.m. - 11:03 p.m.
MDW
-
YYZ
8h 38m
1 stop
Delta Logo
12:09 p.m. - 6:33 p.m.
YYZ
-
MDW
7h 24m
1 stop
C$ 426Delta
Fri, 28 Aug - Fri, 4 Sep
Delta Logo
1:25 p.m. - 11:03 p.m.
MDW
-
YYZ
8h 38m
1 stop
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
C$ 443Delta
Fri, 9 Oct - Mon, 12 Oct
WestJet Logo
1:33 p.m. - 11:06 p.m.
MDW
-
YYZ
8h 33m
1 stop
WestJet Logo
6:05 a.m. - 12:53 p.m.
YYZ
-
MDW
7h 48m
1 stop
C$ 507WestJet
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Toronto Pearson Intl Airport departing in September.

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$ 137 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 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 Sundays.

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 February, where tickets cost C$ 91 (return) on average. On the other hand, the most expensive months are March and September, where the average cost of round-trip tickets is C$ 251 and C$ 226 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 C$ 375, 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 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 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.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on Air Canada and ORD

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.

Mark Stachiew

Mark Stachiew

Expert on YYZ

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.

Good to know

Low seasonFebruary
Cheapest flightC$ 150
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly (2% 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 5 days, the lowest price for a flight from Chicago to Toronto Pearson Intl Airport was C$ 150 for a one-way ticket and C$ 335 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?

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

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

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Chicago to Toronto flight route.

  • Which airline alliances offer flights from Chicago to Toronto?

    Star Alliance is the only airline alliance operating flights between Chicago and Toronto.

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

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

  • 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$ 175 or less one-way and C$ 197 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 airline 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 9926 reviews
6.6Food
7.7Boarding
7.1Entertainment
7.3Comfort
8.1Crew
Airline reviews

Entertainment kept turning itself off. Gave up on watching a movie.

8.0 ExcellentLeslie, Feb 2026
SFO - YYZ
Read more United Airlines reviews

Entertainment kept turning itself off. Gave up on watching a movie.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Not United Airlines' fault. It's ORL airport's fault.

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.

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 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.

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.

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

The male air hostess was rude and didn’t even offer me a drink. Poor customer service!

My only concern was that we were on the tarmac for so long and weren’t told what was happening. It turned out that the system needed to be restarted but it would have been nice to know earlier.

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

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