YYZ - CHI

$120 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 4/15. 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, 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
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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
2:00 pm - 6:53 pmYYZ-ORD
5h 53m1 stop
10:40 am - 5:58 pmORD-YYZ
6h 18m1 stop
$214Air Canada
Find Deal
Fri, Jun 6 - Sun, Jun 8
2:05 pm - 6:54 pmYYZ-ORD
5h 49m1 stop
2:05 pm - 4:45 pmORD-YYZ
1h 40mnonstop
$215Air Canada
Find Deal
Wed, Apr 2 - Sun, Apr 6
7:55 pm - 8:35 amYYZ-ORD
13h 40m1 stop
6:25 pm - 11:55 pmORD-YYZ
28h 30m2 stops
Sat, Mar 22 - Tue, Mar 25
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
6:25 pm - 11:55 pmORD-YYZ
28h 30m2 stops
Sat, Mar 22 - Tue, Mar 25
6:30 am - 6:18 pmYYZ-MDW
12h 48m1 stop
10:25 am - 10:59 pmMDW-YYZ
11h 34m1 stop
$244WestJet
Find Deal
Thu, Mar 20 - Thu, Mar 27
6:30 am - 2:15 pmYYZ-MDW
8h 45m1 stop
10:25 am - 10:59 pmMDW-YYZ
11h 34m1 stop
$245WestJet
Find Deal
Wed, Mar 19 - Wed, Mar 26
8:15 am - 9:10 amYYZ-ORD
1h 55mnonstop
1:00 pm - 3:46 pmORD-YYZ
1h 46mnonstop
$247United Airlines
Find Deal
Sun, May 4 - Mon, May 5
1:15 pm - 2:10 pmYYZ-ORD
1h 55mnonstop
9:45 am - 5:20 pmORD-YYZ
6h 35m1 stop
$258American Airlines
Find Deal
Sat, May 3 - Sat, May 10
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
8:22 am - 3:00 pmORD-YYZ
5h 38m1 stop
$263American Airlines
Find Deal
Sun, Mar 30 - Wed, Apr 2
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
7:12 am - 9:58 amORD-YYZ
1h 46mnonstop
$273United Airlines
Find Deal
Thu, Mar 20 - Mon, Mar 24

Expert advice for your flight from Pearson Intl to Chicago

Our travel pros reveal their best tips for your Pearson Intl to Chicago journey.
Airports
YYZ

Pearson's security lines can be long; arrive early. Check wait times online or use YYZ Express to book a screening slot.

Read more about YYZby Stefanie Waldek
ORD

Take the CTA Blue Line from ORD to downtown Chicago for a 45-minute ride, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD and YYZ

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

Snippets provided in this section are AI-generated based on a summarization 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.

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 $173 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 $173.

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.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Monday. On your return trip to Toronto Pearson Airport, you should consider flying back on a Friday, and avoid Sundays for better 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 $265 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is $342 and $317 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.
No, with an average price for the route of $598, prices are generally cheapest when you fly direct.

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

$120
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Toronto Pearson Airport to Chicago Midway 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 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.

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 $120 for a one-way ticket and $214 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 $366 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 $173 or less one-way and $270 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 direct 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 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 8766 reviews
7.1Entertainment
6.7Food
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

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

10.0 ExcellentSam, Feb 2025GRU - ORD
Read more United Airlines reviews

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

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.

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

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

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

Information on your arrival and departure airports

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