YYZ - CHI

C$ 182 Find Cheap Flights from Toronto Pearson Airport to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pearson Intl to Chicago departing on 19/2. 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
0 bags

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago.
In the last 7 days, travellers have searched 41,299,237 times on KAYAK, and here is why:

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Cheap Flight Deals from Toronto Pearson Airport to Chicago (YYZ-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto Pearson Airport to Chicago 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.

Recent round-trip flight deals from Pearson Intl to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Pearson Intl to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:00 a.m. - 2:23 p.m.YYZ-ORD
8h 23m1 stop
3:16 p.m. - 11:53 p.m.ORD-YYZ
7h 37m1 stop
C$ 342
Find Deal
Fri, 10 Jan - Mon, 27 Jan
7:35 a.m. - 2:48 p.m.YYZ-ORD
8h 13m1 stop
3:16 p.m. - 11:53 p.m.ORD-YYZ
7h 37m1 stop
C$ 343
Find Deal
Thu, 9 Jan - Mon, 27 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
9:49 a.m. - 12:30 p.m.ORD-YYZ
1h 41mdirect
C$ 368American Airlines
Find Deal
Thu, 23 Jan - Sun, 26 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
6:00 a.m. - 11:45 a.m.ORD-YYZ
4h 45m1 stop
C$ 381American Airlines
Find Deal
Thu, 23 Jan - Sun, 26 Jan
6:30 a.m. - 3:30 p.m.YYZ-ORD
10h 00m1 stop
6:15 a.m. - 1:48 p.m.ORD-YYZ
6h 33m1 stop
C$ 402WestJet
Find Deal
Sun, 19 Jan - Sun, 26 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 414Air Canada
Find Deal
Wed, 8 Jan - Fri, 31 Jan
8:00 a.m. - 8:57 a.m.YYZ-ORD
1h 57mdirect
7:20 a.m. - 1:41 p.m.ORD-YYZ
5h 21m1 stop
C$ 421Air Canada
Find Deal
Fri, 24 Jan - Mon, 27 Jan
6:00 a.m. - 9:16 a.m.YYZ-ORD
4h 16m1 stop
4:15 p.m. - 11:07 p.m.ORD-YYZ
5h 52m1 stop
C$ 430WestJet
Find Deal
Fri, 24 Jan - Mon, 3 Feb
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 431United Airlines
Find Deal
Sun, 19 Jan - Wed, 22 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
8:50 a.m. - 2:18 p.m.ORD-YYZ
4h 28m1 stop
C$ 437United Airlines
Find Deal
Tue, 7 Jan - Wed, 8 Jan

Flights from Pearson Intl to Chicago - Travel Insights & Trends

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Toronto Pearson Intl Airport to Chicago.
Our data shows that the cheapest route for a return flight from Toronto Pearson Intl Airport to Chicago cost C$ 379 and was between Toronto Pearson Intl Airport (YYZ) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is C$ 379.

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

The average price of all round-trip flights from Toronto Pearson Intl Airport to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Tuesday, 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 Toronto Pearson Airport to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Chicago, 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 Toronto Pearson Intl Airport to Chicago is April, where tickets cost C$ 343 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is C$ 424 and C$ 417 respectively.

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

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$ 422 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Toronto Pearson Intl Airport to Chicago, 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 Toronto Pearson Intl Airport to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 182
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly (7% more expensive on average)
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

When to book flights from Pearson Intl to Chicago

Are your dates flexible? Find out the best times to travel from Pearson Intl to Chicago 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 Toronto Pearson Airport to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago was C$ 127 for a one-way ticket and C$ 238 for a round-trip.

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

    When flying out of Toronto Pearson Airport you will be using Toronto Pearson Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Toronto Pearson Airport to Chicago flight route.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are United Airlines and American Airlines. With an average price for the route of C$ 453 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 C$ 520 and an overall rating of 7.2.

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

    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 Toronto Pearson Airport to Chicago.

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

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

    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 Chicago with an airline and back to Toronto Pearson Airport with another airline.

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

    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 Chicago from Toronto Pearson Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 344 or less one-way and C$ 629 or less round-trip.

Prefer to fly direct from Toronto Pearson Airport to Chicago?

Find which airlines fly direct from Toronto Pearson Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Chicago

Monday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Tuesday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Wednesday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Thursday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Friday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Saturday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Sunday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

See more nonstop flights

Direct returns

Chicago to Toronto Pearson Intl

Monday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Tuesday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Wednesday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Thursday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Friday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Saturday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Sunday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

See more nonstop flights
See more nonstop flights

Top 5 airlines serving from Pearson Intl to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. 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 Pearson Intl to Chicago? 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 283 reviews
8.0Comfort
8.1Boarding
8.7Crew
7.0Entertainment
7.6Food
Airline reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

10.0 ExcellentJoan, Nov 2024YOW - YYZ
Read more Porter Airlines reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

Cramped seats. Audio jack for the in -flight entertainment was broken.

Flight was great albeit the long line before the int’l immigration given the timing of the year.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

United airlines was top for my last trip in every way

Connection coordination with Star Alliance partner could be better. Lots of check in setup was not interlinked between operators.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Single flights to Cancun purchased through third-party, initially had issues printing luggage labels with the lady at the airport Pearson… Was super friendly and assisted quickly despite being very busy

Very old planes. Seats were not comfortable. Air was not on during the flight leading to incredibly stuffy conditions.

It was so bad experience they wanted just charged passengers for any reason.

The flight was on time and shorter time arrival than planned. I was an ultra basic passenger and understood one personal item on the plane. The announcements of one personal item and zone 9 boarding certainly felt like we were separated from the rest. Actually zone 9 passengers should be boarded second; we are not blocking aisles and can be seated much faster and deboarded faster too.

Still sitting in a hotel when I'm due for work

Delays happen but communication and care were very low on what ended up being a long day.

Never been on a long haul flight that didn't have on flight entertainment. I hope the way back is better !

Very easy boarding. The on board snacks were not good.

They canceled the flight with no reason given they should not be in business

We had a 44 minute layover ( ??? ) to change planes for our flight to SRQ. We landed at Concourse D, and the SRQ plane was located at Concourse B, as we were told in Toronto. We got to "B4" as directed by ( Delta Help ), in less than 10 minutes, only to see the flight we booked to leave at 2:28, was showing "DEPARTED". Back to Delta Help, got an extremely obnoxious and rude clerk who gave use two options, next flight leaving 5:20, on "B12", (STANDBY). or (CONFIRMED), leaving around 8:PM, not sure of the exact time because they took our seat request and gave us another boarding pass minus the exact time. We had been waiting hours for the 5:20 flight and at the very last minute a group appeared and were allowed to board. When the "standby" folks were summoned, several were allowed to board ahead of us, even though we were there much earlier. The clerk, who gave his name as Markus, a black man with a beard, was the most arrogant. rude and condescending individual in existence. When I asked him to repeat his name he said "what did it sound like?". Had I been thinking I would have answered to me it sounded like (markasshole) which is exactly what he was. When we originally got to that gate and asked for advice, he went on and on telling me he could only comment on the flight that was in progress, that ATL was a big airport, and treated us, both, in our 80"s like we were children unable to understand the process, and directly in my face in a loud voice, shouted exactly what we were already aware of. Not one ounce of consideration for our problem, of just trying to get home. When he called out the names of the remaining "standby" people, he left several go before us, even though we were there waiting hours earlier. He called out our names, John and Nubia, looked at us and shouted out that he only had ONE, and with a grin on his face, let another standby board, and told that person that she got the "lucky" last seat, still grinning, meaning we had to wait once again for the later flight. This obviously prejudiced and biased poor excuse of human beings needs to find a job he is better suited for, perhaps dog catcher or janitor, IMHO. This entire fiasco put us home more than 7 hours later than previously indicated on our original and paid for flight schedule. If Kayak continues to offer flights with different concourse locations and with only a 44 minute layover, they might also consider a more reasonable and reliable time frame for layover. It was a horrible experience and considering alternatives to this service is paramount.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

Fantastic. I am low vision and was impressed with how helpful and accommodating the service tam was. It was super appreciated! I was pleasantly surprised about how delicious the food was. Like, “I wish I had more even though I’m no longer hungry” delicious. 100% enjoyable trip.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Flights were on time both ways, such a big plus! Staff was very accommodating and friendly. Question the choice of snacks that, which on both flights was dairy based. Appreciated using bottled water.

Service was excellent, but they ran out of food options by the time they got to my seat (row 36).

The idea of needing to go outside in the winter to board in icy cold temperatures is totally a non starter for me. Seats were very uncomfortable though the leg room not too terrible. Attendants were nice

The experience was good. Flight was on time. Liked how they offered to accept carryon baggage for free before as I was checking in online.

Flight was delayed by 45 min. No problems. Everyone took it in stride.

Crew was friendly and helpful; cabin seemed roomy even in economy class.

The flight attendants that assisted me were exceptionally nice, kind and helpful

Something wrong with the plane so had to deplane and waited over 2 hours to finally leave

AC needs to update their fleet. Too many mechanical issues, dated planes and too many delays

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

was wondreful! just let me know what airline im flying in advance!

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
19/2Wed
1 stop
8h 25mYYZ-ORD
C$ 182
19/2Wed
1 stop
10h 38mYYZ-ORD
C$ 193
22/1Wed
directAmerican Airlines
2h 15mYYZ-ORD
C$ 218
15/1Wed
directAmerican Airlines
2h 15mYYZ-ORD
C$ 234
19/1Sun
directUnited Airlines
1h 51mYYZ-ORD
C$ 236
18/1Sat
2 stopsWestJet
15h 58mYYZ-ORD
C$ 249
19/1Sun
directUnited Airlines
2h 10mYYZ-ORD
C$ 250
21/1Tue
1 stopAir Canada
8h 30mYYZ-ORD
C$ 282
22/1Wed
1 stopWestJet
12h 17mYYZ-MDW
C$ 283
23/3Sun
1 stopAir Canada
6h 45mYYZ-ORD
C$ 292

Search by stops

Search by airline

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Last minute flights from Pearson Intl to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
25/12Wed
directAmerican Airlines
2h 15mYYZ-ORD
25/1Sat
directAmerican Airlines
1h 35mORD-YYZ
C$ 543
25/12Wed
directAmerican Airlines
2h 00mYYZ-ORD
25/1Sat
multi-stopAmerican Airlines
7h 46mORD-YYZ
C$ 558
26/12Thu
multi-stopWestJet
24h 25mYYZ-ORD
29/1Wed
multi-stopWestJet
15h 07mORD-YYZ
C$ 596
26/12Thu
directAir Canada
1h 51mYYZ-ORD
29/1Wed
multi-stopAir Canada
6h 21mORD-YYZ
C$ 606
26/12Thu
multi-stopWestJet
24h 25mYYZ-ORD
29/1Wed
multi-stopWestJet
23h 03mORD-YYZ
C$ 609
25/12Wed
multi-stopDelta
4h 10mYYZ-MDW
25/1Sat
multi-stopDelta
6h 57mMDW-YYZ
C$ 609
23/12Mon
directUnited Airlines
1h 57mYYZ-ORD
6/1Mon
multi-stopUnited Airlines
11h 53mORD-YYZ
C$ 616
23/12Mon
multi-stopUnited Airlines
11h 32mYYZ-ORD
6/1Mon
multi-stopUnited Airlines
15h 34mORD-YYZ
C$ 624
25/12Wed
multi-stopAir Canada
8h 33mYYZ-ORD
29/1Wed
directAir Canada
1h 41mORD-YYZ
C$ 662
23/12Mon
multi-stopDelta
7h 19mYYZ-MDW
25/12Wed
multi-stopDelta
5h 18mMDW-YYZ
C$ 805

Search by stops

Search by airline

Search by price

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

Information on your arrival and departure airports

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