YYZ - CHI

C$ 124 Find Cheap Flights from Toronto Pearson Airport to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pearson Intl to Chicago departing on 24/5. 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.
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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.
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Cheap Flight Deals from Pearson Intl 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 Pearson Intl 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
12:00 p.m. - 12:55 p.m.YYZ-ORD
1h 55mdirect
8:25 p.m. - 11:07 p.m.ORD-YYZ
1h 42mdirect
C$ 124Air Canada
Find Deal
Sat, 24 May - Sat, 7 Jun
4:00 p.m. - 8:12 p.m.YYZ-ORD
5h 12m1 stop
8:25 p.m. - 11:07 p.m.ORD-YYZ
1h 42mdirect
C$ 203Air Canada
Find Deal
Sat, 24 May - Sat, 7 Jun
7:55 p.m. - 8:35 a.m.YYZ-ORD
13h 40m1 stop
6:25 p.m. - 11:55 p.m.ORD-YYZ
28h 30m2 stops
C$ 318
Find Deal
Sat, 22 Mar - Tue, 25 Mar
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
6:25 p.m. - 11:55 p.m.ORD-YYZ
28h 30m2 stops
C$ 324
Find Deal
Sat, 22 Mar - Tue, 25 Mar
6:30 a.m. - 6:33 p.m.YYZ-MDW
13h 03m1 stop
1:16 p.m. - 11:34 a.m.MDW-YYZ
21h 18m1 stop
C$ 347WestJet
Find Deal
Sat, 12 Apr - Mon, 21 Apr
6:30 a.m. - 2:15 p.m.YYZ-MDW
8h 45m1 stop
10:25 a.m. - 10:59 p.m.MDW-YYZ
11h 34m1 stop
C$ 348WestJet
Find Deal
Wed, 19 Mar - Wed, 26 Mar
9:00 a.m. - 10:01 a.m.YYZ-ORD
2h 01mdirect
1:00 p.m. - 3:46 p.m.ORD-YYZ
1h 46mdirect
C$ 351United Airlines
Find Deal
Sun, 4 May - Thu, 8 May
1:15 p.m. - 2:10 p.m.YYZ-ORD
1h 55mdirect
9:45 a.m. - 5:20 p.m.ORD-YYZ
6h 35m1 stop
C$ 367American Airlines
Find Deal
Sat, 3 May - Sat, 10 May
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
8:22 a.m. - 3:00 p.m.ORD-YYZ
5h 38m1 stop
C$ 374American Airlines
Find Deal
Sun, 30 Mar - Wed, 2 Apr
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
9:12 p.m. - 11:59 p.m.ORD-YYZ
1h 47mdirect
C$ 386United Airlines
Find Deal
Thu, 20 Mar - Mon, 24 Mar

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$ 311 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$ 311.

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 Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday 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$ 376 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is C$ 486 and C$ 450 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$ 1,086 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 10 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 124
Best time to beat the crowds (3% less expensive on average)
Most popular time to fly (6% 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.

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

Insights shared by verified travellers 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.

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$ 120 for a one-way ticket and C$ 87 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, 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 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$ 455 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$ 511 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$ 245 or less one-way and C$ 471 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, +13 more

ANA,Air Canada, +14 more

Tuesday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Wednesday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Thursday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Friday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Saturday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Sunday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

See more nonstop flights

Direct 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 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 276 reviews
7.6Food
8.2Boarding
8.7Crew
8.0Comfort
6.9Entertainment
Airline reviews

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

4.0 OkayJason, Feb 2025YHZ - YUL
Read more Porter Airlines reviews

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

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

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

Everything was good. Flight was on time, luggage pickup was quick. The staff were great. Could not ask for anything more.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

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

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Flight delayed, missed connection, had to stay overnight. Next flight instead of our business class we were booked on the very back row. Second time this had happened in 2 months.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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.

Flight cancelled and Kayak switched our return flight to a red eye. Ridiculous.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

Lost my luggage. Filed a report and there is no response. Received a phone call from another airline that said they had the bag and they did not know what to do with it

Very good over all , would have been nice to have entertainment on the flight

Absolutely the worst airline I have ever taken. They lost my baggage and told me my bag tags had been cancelled. When my bags arrived days later I had to pick them up at 3:15 am. My return flight was delayed another 6 hours and they broke my bag. Westjet does nothing to try and make it a better customer experience and all the customers services representatives I spoke with were useless and incompetent. Never flying westjet again.

Easy self checkin and baggage drop. No in seat entertainment, but wifi and app worked well

it's all good nothing you can do make better 😌

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.

My flight was cancelled and I was left to figure out where to find a hotel, something to eat and how to get a new flight at 11:30pm. Wasted a day. Thanks, Air Canada!

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

They kept changing the gate (6 times in 30 minutes) and then left us on the plane for 4 hours before departure. Likely was the storm, which is understandable, but the lack of communication and the e constant running between gates at opposite ends of the airport really threw me and my friend for a loop.

Legitimately everything about this flight was awful, was also so delayed I never want to use air Canada again

Terrible all around. Flight was late and airplane was very uncomfortable. The crew were unhelpful and hid in the back. Did zero work. No entertainment.

I like the free beer and wine but not the delays to the departure time.

Never again flying economy on Rouge!!! Literally like sardines!!! Will try to change to better seats 3 seat arrangement only so so if traveling with family. Who wants to squished to stranger!!😖 Can’t say enough bad about this!!!

I booked and paid extra for exit door seats also pre paid for my luggage air Canada changed plains and I never got what I paid for and they made me pay for luggage again they also did this to my wife. They are the most unorganized company I have ever dealt with. I am sure I will never see the extra money I paid for the seats or the recharge for the luggage. They are subsidized by the taxpayers and don’t give a dam just a horrible way to do business

Overall the experience was excellent. Plane was clean but more importantly quiet. Recently, I’ve noticed that Airbus planes seem quieter than their Boeing counterparts. I definitely prefer flying in an Airbus plane.

Delay after delay.......they are awful Delayed because of cold wx really!!!!! We live in Canada

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Porter

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