YYZ - CHI

$135 Find Cheap Flights from Toronto Pearson Airport to Chicago - Compare and Save

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 7/2. 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, 0 bags

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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$207
Typical prices: $437-$230
American Airlines
Thu 9/24Sun 9/27
YYZ - ORD • Non-stop
Cheapest non-stop
$207
Typical prices: $441-$230
United Airlines, Air Canada
Wed 9/9Mon 9/14
YYZ - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
Qatar Airways Economy adds a free checked bag; Air Canada Preferred Economy adds legroom.
United Premier Access speeds check-in; American Main Cabin Extra adds boarding perks.
Expert advice
Expert advice
+1
+1
Expert advice
Expert advice
+1
Top airlines
Cheapest • from $206 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Air Canada, American Airlines and United Airlines. Average duration is 2h 01m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 92% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 67% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
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, Sep 24 - Sun, Sep 27
American Airlines Logo
6:30 am - 7:40 am
YYZ
-
ORD
2h 10mnonstop
American Airlines Logo
8:30 pm - 11:26 pm
ORD
-
YYZ
1h 56mnonstop
$207American Airlines
Thu, Sep 24 - Sat, Sep 26
Air Canada Logo
6:15 am - 10:17 am
YYZ
-
ORD
5h 02m
1 stop
Air Canada Logo
5:35 pm - 8:18 pm
ORD
-
YYZ
1h 43mnonstop
$208Air Canada
Thu, Jul 2 - Sun, Jul 5
Air Canada Logo
4:00 pm - 4:57 pm
YYZ
-
ORD
1h 57mnonstop
Air Canada Logo
9:50 am - 12:35 pm
ORD
-
YYZ
1h 45mnonstop
$209Air Canada
Sat, Sep 19 - Sun, Sep 20
Air Canada Logo
6:15 am - 10:17 am
YYZ
-
ORD
5h 02m
1 stop
Air Canada Logo
5:35 pm - 8:18 pm
ORD
-
YYZ
1h 43mnonstop
$210Air Canada
Fri, Sep 11 - Mon, Sep 14
Delta Logo
9:45 am - 4:57 pm
YYZ
-
MDW
8h 12m
1 stop
Delta Logo
9:30 am - 1:34 pm
MDW
-
YYZ
3h 04m
1 stop
$240Delta
Wed, Jul 15 - Wed, Jul 22
KLM Logo
6:10 am - 9:13 am
YYZ
-
MDW
4h 03m
1 stop
KLM Logo
9:19 am - 5:24 pm
MDW
-
YYZ
7h 05m
1 stop
$243KLM
Fri, Jul 10 - Tue, Jul 28
Delta Logo
12:09 pm - 6:25 pm
YYZ
-
MDW
7h 16m
1 stop
Delta Logo
9:19 am - 5:24 pm
MDW
-
YYZ
7h 05m
1 stop
$244Delta
Tue, Sep 1 - Sun, Sep 13
Delta Logo
12:09 pm - 4:59 pm
YYZ
-
MDW
5h 50m
1 stop
Delta Logo
5:59 pm - 10:57 pm
MDW
-
YYZ
3h 58m
1 stop
$246Delta
Sat, Aug 8 - Mon, Aug 10
WestJet Logo
12:14 pm - 6:38 pm
YYZ
-
MDW
7h 24m
1 stop
WestJet Logo
1:32 pm - 11:08 pm
MDW
-
YYZ
8h 36m
1 stop
$257WestJet
Tue, Jun 30 - Mon, Jul 6
WestJet Logo
12:14 pm - 6:36 pm
YYZ
-
MDW
7h 22m
1 stop
WestJet Logo
1:31 pm - 11:07 pm
MDW
-
YYZ
8h 36m
1 stop
$269WestJet
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Toronto Pearson Intl Airport to Chicago departing in September.

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 $232 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 Friday 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 January, where tickets cost $51 (return) on average. On the other hand, the most expensive months are August and April, where the average cost of round-trip tickets is $688 and $183 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 $319, 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 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Pearson Intl to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Qatar Airways, Air Canada, United Airlines, ORD and YYZ

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Good to know

Low seasonDecember
Cheapest flight$135
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly with an average 2% 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 Canada
YYZ
-
ORD
Oct 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 Airlines
YYZ
-
ORD
Mar 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 5 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago was $135 for a one-way ticket and $206 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 Air Canada?

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are United Airlines and Air Canada. With an average price for the route of $256 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of $257 and an overall rating of 7.1.

  • 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 $206 or less one-way and $324 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 9830 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
6.6Food
8.1Crew
Airline reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarding was smooth and efficient. The only food was some pretzels, but it was a short flight. Not much to order if you were hungry.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Awful customer service, horrible experience. We travel a lot domestic & international- worst flights to/from ever. Brief bkgd as Inhate to relive this experience: booked and chose 2 seats 4 months prior in Premium Economy - last row end seats close to bathroom, no one behind us, plenty of legroom;, underwear storage — flown this was on other airlines, love it. We receive notice 4 days before scheduled overseas flight - plane has changed, new seats assigned. Seats are split into single seats, opposites of the plane, FRONT Row so no reachable storage. Called BOTH British Air & America. American “switched planes and the seats you want are taken;” British Air “Yes, we’ll be glad to accommodate you (type type type). Just ask at the Gate and someone will give you new boarding passes with seats together in middle, OK?” — OK. —At Gate the attendant looks us up saying “No, it is an overbooked flight and yours are the only seats available.” But but but wait, “We were TOLD our seats had been switched and seated together?” Gate attendant “Well they were wrong and don’t change your seats. Your original seats are where you’ll sit.”. Right. No help WHATSOEVER. We sit opposite on way there, wife VERY disgruntled, a Tol 5 worst ways to start a 3-week bus tour of UK. We promise to NEVER FLY AMERICAN OR BROTISH AIR EVER, and we have 3 more extensive trips planned..

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

It was a nice and smooth trip. Gave a friendly environment throughout the journey.

Meal and drink service was good. Old plane with old business class seats were quite disappointing

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

My seat was covered in vomit and I will be reaching out to Air Canada

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

Information on your arrival and departure airports