YYZ - CHI

$113 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 10/1. 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

KAYAK searches 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
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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pearson Intl to Chicago

Thu, Oct 2 - Mon, Oct 6
Air Canada Logo
8:15 am - 9:09 amYYZ-ORD
1h 54mnonstop
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
$175Air Canada
Find Deal
Thu, Oct 2 - Mon, Oct 6
Air Canada Logo
8:15 am - 9:09 amYYZ-ORD
1h 54mnonstop
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
$177Air Canada
Find Deal
Thu, Oct 2 - Mon, Oct 6
Air Canada Logo
6:15 am - 9:51 amYYZ-ORD
4h 36m1 stop
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
$178Air Canada
Find Deal
Fri, Oct 24 - Fri, Oct 31
Air Canada Logo
6:15 am - 9:51 amYYZ-ORD
4h 36m1 stop
Air Canada Logo
2:00 pm - 4:39 pmORD-YYZ
1h 39mnonstop
$180Air Canada
Find Deal
Sun, Nov 23 - Sun, Nov 30
United Airlines Logo
6:50 am - 7:55 amYYZ-ORD
2h 05mnonstop
United Airlines Logo
7:10 am - 9:58 amORD-YYZ
1h 48mnonstop
$186United Airlines
Find Deal
Fri, Oct 3 - Mon, Oct 6
United Airlines Logo
9:00 am - 9:55 amYYZ-ORD
1h 55mnonstop
United Airlines Logo
9:12 pm - 11:58 pmORD-YYZ
1h 46mnonstop
$187United Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
 Logo
8:15 am - 9:09 amYYZ-ORD
1h 54mnonstop
 Logo
8:00 am - 5:14 pmORD-YYZ
8h 14m1 stop
Thu, Oct 2 - Mon, Oct 6
Lufthansa Logo
2:45 pm - 3:48 pmYYZ-ORD
2h 03mnonstop
Lufthansa Logo
9:12 pm - 11:58 pmORD-YYZ
1h 46mnonstop
$215Lufthansa
Find Deal
Mon, Oct 13 - Thu, Oct 23
 Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
 Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
Sat, Oct 4 - Mon, Oct 6
American Airlines Logo
7:35 am - 2:06 pmYYZ-ORD
7h 31m1 stop
American Airlines Logo
5:22 am - 11:10 amORD-YYZ
4h 48m1 stop
$229American Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts and KAYAK users
Air Canada's Preferred Economy offers extra legroom.
United's carry-on size is smaller for US-bound flights.
Expert advice
Expert advice
+1
+1
Expert advice
Expert advice
+1
Top airlines
Air Canada
Cheapest • from $175 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
YYZ-ORD
Cheapest
YYZ-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 11% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$175
Typical prices: $265-360
Air Canada
Thu 10/2Mon 10/6
YYZ - ORD • Non-stop
Cheapest one-way
$113
Typical prices: $140-223
Air Canada
Wed 10/1
YYZ - ORD • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Pearson Intl to Chicago

 
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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Qatar Airways

Qatar Airways' Economy tickets include a free checked bag, enhancing value for short-haul flights.


Qatar Airways offers Wi-Fi on most aircraft, though some routes may have blackout zones.

Air Canada

Air Canada's Preferred Economy seats offer up to four extra inches of legroom.


Air Canada's Wi-Fi offers free messaging for Aeroplan members; full internet costs extra.

Read more about Air Canadaby Stefanie Waldek
United Airlines

United's Premier Access offers priority check-in and bag tags for faster airport processing.


United's Wi-Fi offers free messaging; T-Mobile customers get complimentary streaming.

American Airlines

American Airlines' Main Cabin Extra offers early boarding and complimentary drinks.


American Airlines provides 20 minutes of free Wi-Fi by watching a short advertisement.

Airports
YYZ

Pearson's security lines can be long, so arrive early. Check wait times online or use YYZ Express for a faster experience.

Read more about YYZby Stefanie Waldek
ORD

Take the CTA Blue Line from ORD to downtown Chicago. It's a 45-minute ride and runs 24 hours, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Qatar Airways, Air Canada, United Airlines, 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
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Booking Insights

KAYAK's insights & trends for Pearson Intl to Chicago flights

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.

How much is a round-trip flight from Toronto Pearson Intl Airport to Chicago?

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Toronto Pearson Intl Airport to Chicago costs $182 on the route between Toronto Pearson Intl Airport (YYZ) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 Saturday and more expensive on a Monday. On your return trip to Toronto Pearson Airport, you should consider flying back on a Thursday, 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 May, where tickets cost $253 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $338 and $302 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 $286, 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 4 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$113
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 5% 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.

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.
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

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 $113 for a one-way ticket and $175 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, 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 De Havilland (Bombardier) DHC-8-400 Dash 8Q 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 $258 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 $354 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.

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 $260 or less one-way and $390 or less round-trip.

Prefer to fly direct from Toronto Pearson Airport to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Pearson Intl 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

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 direct flights

Direct returns

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 direct flights

Reviews of the 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 8937 reviews
7.7Boarding
7.1Entertainment
6.6Food
7.3Comfort
8.1Crew
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Good service, friendly staff. Food was average for airlines and the seats were small.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

I liked the behaviour of the crew members.The flight was good.

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

Horrible flight cancelled had to buy another very expensive ticket

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

Terrible, return flight was cancelled a night before the flight was scheduled to depart and I was notified by an email and an automated message on their phone line. I’ll never book Air Canada again

Biggest problem for me is that I am Star Alliance Gold and they were not able to give me access to to Maple Lounge because of some computer glitch . It was management by information system. She could clearly see my status and still would not give me access because the computer woudl not let her. She should have override that be attentive to a customer and figure rhat out later

Great breakfast and coffee …..fastest bag service I have ever had in NOLA

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

Information on your arrival and departure airports

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