YYZ - CHI

$144 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 12/17. 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

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, 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 Toronto to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 46,646,933 times on KAYAK, and here is why:

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

 
These are the cheapest deals for flights from Pearson Intl to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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
9:00 am - 10:05 amYYZ-ORD
2h 05mnonstop
6:38 pm - 9:25 pmORD-YYZ
1h 47mnonstop
$237United Airlines
Find Deal
Sat, Dec 7 - Mon, Dec 9
2:05 pm - 6:36 pmYYZ-ORD
5h 31m1 stop
6:38 pm - 9:25 pmORD-YYZ
1h 47mnonstop
$244Air Canada
Find Deal
Sat, Dec 7 - Mon, Dec 9
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
8:25 pm - 11:06 pmORD-YYZ
1h 41mnonstop
$245United Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
5:30 pm - 6:37 pmYYZ-ORD
2h 07mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$246Air Canada
Find Deal
Fri, Dec 13 - Sun, Dec 15
2:45 pm - 1:20 pmYYZ-MDW
23h 35m1 stop
9:20 am - 10:58 pmMDW-YYZ
12h 38m1 stop
$273WestJet
Find Deal
Fri, Apr 11 - Sun, Apr 20
10:05 am - 5:01 pmYYZ-MDW
7h 56m1 stop
5:50 pm - 10:36 pmMDW-YYZ
3h 46m1 stop
$275Delta
Find Deal
Thu, Dec 12 - Mon, Dec 16
2:45 pm - 12:46 pmYYZ-MDW
23h 01m1 stop
6:59 pm - 1:48 pmMDW-YYZ
17h 49m1 stop
$283WestJet
Find Deal
Tue, Jan 7 - Sat, Jan 11
2:55 pm - 10:25 pmYYZ-ORD
8h 30m1 stop
10:30 am - 4:12 pmORD-YYZ
4h 42m1 stop
$287Delta
Find Deal
Sat, Dec 14 - Fri, Jan 10
6:00 am - 10:33 amYYZ-ORD
5h 33m1 stop
7:00 am - 3:45 pmORD-YYZ
7h 45m1 stop
$293American Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
1:14 pm - 2:14 pmYYZ-ORD
2h 00mnonstop
8:05 am - 3:45 pmORD-YYZ
6h 40m1 stop
$295American Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15

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 one-way flights from Toronto Pearson Intl Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from Toronto Pearson Intl Airport to Chicago cost $145 and was between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $229.

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

The average price of all flights from Toronto Pearson Intl Airport to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Toronto Pearson Airport to Chicago, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Toronto Pearson Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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 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 $239 on average. On the other hand, the most expensive months are November and August, where the average cost of tickets is $307 and $287 respectively.

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

The average 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 2 stops layover the cheapest option at $301 on average

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 124 days before departure.

Good to know

Low season

January

High season

August

Cheapest flight

$144
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 8% increase in price.
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 $144 for a one-way ticket and $237 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Toronto Pearson Airport and on arrival in Chicago.

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

    On your way to Chicago, you’ll fly out from Toronto Pearson Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

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

    Air Canada, and United 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 nonstop 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 $290 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 $361 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 travelers 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 $219 or less one-way and $306 or less round-trip.

Flights from Pearson Intl to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Pearson Intl to Chicago 
BrianFlew with Air CanadaYYZ-ORDOct 2024
Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.
Jo AnnFlew with Air CanadaYYZ-ORDJun 2024
It seemed that anyone who checked a bag was able to retrieve it quickly.
Verified travelerFlew with United AirlinesYYZ-ORDMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time
Verified travelerFlew with Air CanadaYYZ-ORDFeb 2024
I would definitely choose Air Canada over dirty old United airplanes any day.
Verified travelerFlew with United AirlinesYYZ-ORDDec 2023
The departure time was very convenient with the United.

Prefer to fly non-stop 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.

Nonstop 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 direct flights

Nonstop returns

Chicago to Toronto Pearson Intl

Monday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Tuesday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Wednesday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Thursday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Friday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Saturday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

Sunday

ANA, Air Canada, Air New Zealand, +11 more

ANA, Air Canada, +12 more

See more direct flights
See more direct flights

Top 3 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.
7.4
United AirlinesOverall score based on 9172 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.7Food
8.1Crew
Airline reviews

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

2.0 MediocreMichael, Nov 2024MSY - ORD
Read more United Airlines reviews

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

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

The plane used to go to Chicago was a bit outdated and needed a refresh

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.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

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!

On this flight, we didn't even get water offered, nor any other beverage. Therefore we got a snack of pretzels. Flight was good and Air Canada a good airline

I would realllllly like to have been in a seat closer than row FORTY. Needing assistance - longgg way to walk down and back; then they put me in the middle seat-needing to get up for the window seat passenger to go to the washroom etc.

Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!

The flight was delayed but at least they let us know early about it (the night before)! Everything after that was smooth!

Our seats were changed 3 times in the final 24 hours, and then my wife and I ended up with two middle seats in different rows. Full flight so no changes could be made at the gate.

Air Canada was on schedule, fast, and took care of me the whole flight. With affordable price, I 100% recommend you fly Air Canada if you are able to.

I book my air canada flight and i am an aeroplan card holder however I was required to pay for my first check-in bag. Terrible experience

Multiple change of the gates at Pearson, delayed flight was extremely uncomfortable.

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.
12/17Tue
nonstopAir Canada
2h 07mYYZ-ORD
$144
12/18Wed
nonstopAir Canada
1h 57mYYZ-ORD
$147
12/18Wed
1 stopUnited Airlines
7h 16mYYZ-ORD
$152
12/13Fri
nonstopUnited Airlines
2h 07mYYZ-ORD
$159
12/4Wed
1 stop
13h 24mYYZ-ORD
$162
2/4Tue
1 stop
10h 30mYYZ-ORD
$168
1/6Mon
1 stopDelta
3h 58mYYZ-MDW
$176
2/12Wed
nonstopAmerican Airlines
2h 00mYYZ-ORD
$181
12/8Sun
1 stopDelta
7h 56mYYZ-MDW
$184
12/23Mon
nonstopAmerican Airlines
2h 00mYYZ-ORD
$186

Search by stops

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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.
11/25Mon
nonstopAmerican Airlines
2h 00mYYZ-ORD
12/9Mon
multi-stopAmerican Airlines
4h 50mORD-YYZ
$401
11/26Tue
nonstopAmerican Airlines
2h 00mYYZ-ORD
12/4Wed
multi-stopAmerican Airlines
4h 58mORD-YYZ
$405
11/26Tue
multi-stopWestJet
4h 37mYYZ-MDW
12/3Tue
multi-stopWestJet
13h 11mMDW-YYZ
$405
11/25Mon
multi-stop
12h 46mYYZ-ORD
11/29Fri
multi-stop
7h 01mORD-YYZ
$410
11/26Tue
nonstopAir Canada
1h 51mYYZ-ORD
1/21Tue
nonstopAir Canada
1h 41mORD-YYZ
$415
11/26Tue
multi-stopWestJet
9h 10mYYZ-ORD
11/28Thu
multi-stopWestJet
6h 24mORD-YYZ
$419
11/24Sun
multi-stopAir Canada
5h 29mYYZ-ORD
12/3Tue
multi-stopAir Canada
5h 21mORD-YYZ
$420
11/25Mon
multi-stop
9h 31mYYZ-ORD
12/9Mon
multi-stop
35h 10mORD-YYZ
$433
11/23Sat
nonstopUnited Airlines
1h 57mYYZ-ORD
12/1Sun
nonstopUnited Airlines
1h 39mORD-YYZ
$473
11/22Fri
nonstopUnited Airlines
2h 07mYYZ-ORD
11/25Mon
nonstopUnited Airlines
1h 45mORD-YYZ
$504

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

Information on your arrival and departure airports

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