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 2/25. 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
$187
Typical prices: $241-$341
Air Canada
Thu 2/19Mon 2/23
YYZ - ORD • Non-stop
Cheapest one-way
$120
Typical prices: $153-$307
Air Canada
Wed 2/25
YYZ - ORD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
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 $187 (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 52% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 13% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
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, Feb 19 - Mon, Feb 23
Air Canada Logo
2:15 pm - 3:10 pm
YYZ
-
ORD
1h 55mnonstop
Air Canada Logo
8:00 am - 10:40 am
ORD
-
YYZ
1h 40mnonstop
$187Air Canada
Wed, Feb 18 - Sat, Feb 21
Air Canada Logo
10:00 am - 2:55 pm
YYZ
-
ORD
5h 55m
1 stop
Air Canada Logo
7:15 am - 1:40 pm
ORD
-
YYZ
5h 25m
1 stop
$189Air Canada
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
3:30 pm - 4:39 pm
YYZ
-
ORD
2h 09mnonstop
United Airlines Logo
6:28 pm - 9:21 pm
ORD
-
YYZ
1h 53mnonstop
$190United Airlines
Thu, Feb 19 - Mon, Feb 23
Air Canada Logo
8:00 am - 2:55 pm
YYZ
-
ORD
7h 55m
1 stop
Air Canada Logo
10:00 am - 12:40 pm
ORD
-
YYZ
1h 40mnonstop
$193Air Canada
Thu, Feb 19 - Mon, Feb 23
Lufthansa Logo
3:30 pm - 4:39 pm
YYZ
-
ORD
2h 09mnonstop
Lufthansa Logo
6:28 pm - 9:21 pm
ORD
-
YYZ
1h 53mnonstop
$198Lufthansa
Fri, Feb 20 - Thu, Feb 26
United Airlines Logo
3:30 pm - 4:39 pm
YYZ
-
ORD
2h 09mnonstop
United Airlines Logo
6:00 am - 11:48 am
ORD
-
YYZ
4h 48m
1 stop
$199United Airlines
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
6:00 am - 7:15 am
YYZ
-
ORD
2h 15mnonstop
American Airlines Logo
6:08 am - 11:51 am
ORD
-
YYZ
4h 43m
1 stop
$200American Airlines
Fri, Mar 6 - Sun, Mar 8
American Airlines Logo
1:55 pm - 6:24 pm
YYZ
-
ORD
5h 29m
1 stop
American Airlines Logo
1:22 pm - 4:03 pm
ORD
-
YYZ
1h 41mnonstop
$205American Airlines
Thu, Feb 19 - Sat, Feb 21
Delta Logo
7:45 am - 12:46 pm
YYZ
-
MDW
6h 01m
1 stop
Delta Logo
5:00 pm - 11:11 pm
MDW
-
YYZ
5h 11m
1 stop
$225Delta
Sat, Feb 21 - Sun, Feb 22
Delta Logo
6:30 am - 11:03 am
YYZ
-
MDW
5h 33m
1 stop
Delta Logo
1:28 pm - 10:40 pm
MDW
-
YYZ
8h 12m
1 stop
$226Delta
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.

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 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 September, where tickets cost $231 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $325 and $283 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 $250, 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 52% 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$120
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

When to book flights from Pearson Intl to Chicago

Are your dates flexible? Find out the best times to travel from Pearson Intl to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

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

Insights shared by verified 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 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago was $120 for a one-way ticket and $187 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 Embraer 195 E2 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 $257 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 $307 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 $217 or less one-way and $313 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 9207 reviews
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
7.3Comfort
Airline reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

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

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff was great and made the long trip easy peasy!

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

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

Information on your arrival and departure airports