YYZ - CHI

$131 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 4/29. 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

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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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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Pearson Intl to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
10:00 am - 10:54 amYYZ-ORD
1h 54mnonstop
8:25 pm - 11:07 pmORD-YYZ
1h 42mnonstop
$213Air Canada
Find Deal
qua, mai 14 - qua, mai 21
9:00 am - 10:01 amYYZ-ORD
2h 01mnonstop
4:00 pm - 6:42 pmORD-YYZ
1h 42mnonstop
$215Air Canada
Find Deal
qua, abr 30 - qui, mai 1
7:15 am - 2:47 pmYYZ-ORD
8h 32m2 stops
8:25 pm - 11:07 pmORD-YYZ
1h 42mnonstop
$218Air Canada
Find Deal
qua, mai 14 - qua, mai 21
7:00 am - 8:03 amYYZ-ORD
2h 03mnonstop
7:20 am - 1:39 pmORD-YYZ
5h 19m1 stop
qui, abr 24 - dom, abr 27
7:00 am - 8:03 amYYZ-ORD
2h 03mnonstop
9:02 am - 11:49 amORD-YYZ
1h 47mnonstop
$245Lufthansa
Find Deal
qui, abr 24 - dom, abr 27
6:00 pm - 11:40 pmYYZ-ORD
6h 40m1 stop
7:20 am - 1:39 pmORD-YYZ
5h 19m1 stop
qui, abr 24 - dom, abr 27
12:00 pm - 12:55 pmYYZ-ORD
1h 55mnonstop
8:50 am - 5:09 pmORD-YYZ
7h 19m1 stop
$253United Airlines
Find Deal
qui, mai 1 - dom, mai 4
6:00 pm - 11:40 pmYYZ-ORD
6h 40m1 stop
9:31 pm - 10:04 amORD-YYZ
11h 33m1 stop
$254United Airlines
Find Deal
qui, abr 24 - seg, jun 16
3:10 pm - 4:05 pmYYZ-ORD
1h 55mnonstop
4:00 pm - 9:30 pmORD-YYZ
4h 30m1 stop
$264American Airlines
Find Deal
ter, mai 27 - qua, jun 4
3:14 pm - 4:09 pmYYZ-ORD
1h 55mnonstop
5:10 am - 11:05 amORD-YYZ
4h 55m1 stop
$266American Airlines
Find Deal
qui, abr 24 - dom, abr 27

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
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.

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.

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 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

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.

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 $187 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 $182.

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 $320 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 $739 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 13 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

$131
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 7% 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.
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 $131 for a one-way ticket and $213 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 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 $289 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 $360 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 $182 or less one-way and $276 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

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
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 8614 reviews
8.1Crew
7.0Entertainment
6.6Food
7.3Comfort
7.7Boarding
Airline reviews

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

6.0 GoodAnonymous, Mar 2025YYZ - LAX
Read more United Airlines reviews

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

headphone jack didnt work for the first flight and not much variety

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 plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

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.

Ensure prepaid food arrangements are appropriately understood by flight crew of who purchased and who did not

All was fine. Weather was a bit stormy, but nothing kayak can do about that! 😊

I paid for a comfort class seat and was seated in economy.

My plane was cancelled and had to be rebook for the evening was not happy.

The flight was cancelled and we had to rebook on Porter to make our cruise the next day. Air Canada has not compensated. We won’t be flying with them again. This is the second time this has happened. Also the return flight was delayed 2 hours who knows why.

Separated me and my wife and wife’s sister in far apart different seats even though I booked them all together. Just scams after scams to make us pay more. Worst airline

If you want your flight to get delayed constantly for 13+ hours and given a 10 dollar food voucher the. I would say take air canada. Worst experience ever.

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.

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

Information on your arrival and departure airports

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