CHI - YYZ

C$ 116 Find Cheap Flights from Chicago to Toronto

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Pearson Intl departing on 10/3. 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 Toronto Pearson Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, 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 Chicago to Toronto, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 274
Overall average: C$ 353
Air Canada
Fri 27/2Sun 1/3
ORD - YYZ • Direct
Cheapest one-way flights
C$ 116
Typical prices: C$ 211-C$ 481
Air Canada
Tue 10/3
ORD - YYZ • Direct
Our travellers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy has late boarding and no free bags.
Use the Union Pearson Express for a quick ride to Toronto.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Air Canada
Cheapest • from C$ 274 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
YYZ
Cheapest
ORD
-
YYZ
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 55% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 17% 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 hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Pearson Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Pearson Intl (CHI-YYZ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Pearson Intl 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 Chicago to Pearson Intl

Fri, 27 Feb - Sun, 1 Mar
Air Canada Logo
8:00 a.m. - 10:40 a.m.
ORD
-
YYZ
1h 40mdirect
Air Canada Logo
12:05 p.m. - 1:01 p.m.
YYZ
-
ORD
1h 56mdirect
C$ 274Air Canada
Sat, 28 Feb - Sun, 1 Mar
Air Canada Logo
2:00 p.m. - 4:39 p.m.
ORD
-
YYZ
1h 39mdirect
Air Canada Logo
2:15 p.m. - 3:10 p.m.
YYZ
-
ORD
1h 55mdirect
C$ 275Air Canada
Wed, 11 Mar - Wed, 18 Mar
Air Canada Logo
8:40 p.m. - 11:19 p.m.
ORD
-
YYZ
1h 39mdirect
Air Canada Logo
8:15 a.m. - 9:13 a.m.
YYZ
-
ORD
1h 58mdirect
C$ 279Air Canada
Thu, 2 Apr - Sun, 5 Apr
Delta Logo
9:35 a.m. - 5:17 p.m.
MDW
-
YYZ
6h 42m
1 stop
Delta Logo
6:20 a.m. - 12:29 p.m.
YYZ
-
MDW
7h 09m
1 stop
C$ 354Delta
Tue, 17 Mar - Sat, 21 Mar
Delta Logo
9:35 a.m. - 3:08 p.m.
MDW
-
YYZ
4h 33m
1 stop
Delta Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
C$ 355Delta
Wed, 11 Mar - Wed, 18 Mar
Multiple Airlines Logo
11:25 a.m. - 12:14 a.m.
MDW
-
YYZ
35h 49m
2 stops
Multiple Airlines Logo
6:20 p.m. - 1:02 p.m.
YYZ
-
MDW
19h 42m
1 stop
C$ 410Multiple Airlines
Thu, 2 Apr - Sun, 5 Apr
KLM Logo
9:35 a.m. - 3:08 p.m.
MDW
-
YYZ
4h 33m
1 stop
KLM Logo
6:20 a.m. - 12:29 p.m.
YYZ
-
MDW
7h 09m
1 stop
C$ 422KLM
Tue, 3 Mar - Thu, 5 Mar
Multiple Airlines Logo
7:30 a.m. - 7:35 p.m.
MDW
-
YYZ
11h 05m
2 stops
Multiple Airlines Logo
7:10 a.m. - 2:26 p.m.
YYZ
-
MDW
8h 16m
1 stop
C$ 436Multiple Airlines
Thu, 2 Apr - Sun, 5 Apr
WestJet Logo
1:10 p.m. - 5:17 p.m.
MDW
-
YYZ
3h 07m
1 stop
WestJet Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
C$ 440WestJet
Wed, 8 Jul - Sat, 18 Jul
WestJet Logo
1:00 p.m. - 5:23 p.m.
MDW
-
YYZ
3h 23m
1 stop
WestJet Logo
3:55 p.m. - 6:31 p.m.
YYZ
-
MDW
3h 36m
1 stop
C$ 445WestJet
Booking Insights

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

Get data-powered insights and trends into flights from Chicago to Pearson Intl to help you find the cheapest flights, the best time to fly and much more.

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

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

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

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

The cheapest return flight from Chicago to Toronto Pearson Intl Airport costs C$ 106 on the route between Chicago O'Hare Intl Airport (ORD) and Toronto Pearson Intl Airport (YYZ). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Toronto?

The average price of all round-trip flights from Chicago to Toronto Pearson Intl Airport clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Toronto, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Tuesdays.

What is the cheapest month to fly from Chicago to Toronto Pearson Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Toronto Pearson Intl Airport, 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 Chicago to Toronto Pearson Intl Airport is June, where tickets cost C$ 328 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is C$ 519 and C$ 456 respectively.

Can I save money by flying with a layover from Chicago to Toronto Pearson Intl Airport?

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 C$ 341, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Toronto Pearson Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Toronto Pearson Intl Airport, 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 Chicago to Toronto Pearson Intl Airport, you should book around 4 weeks before departure, which saves you about 55% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Chicago to Pearson Intl

 
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
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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada and ORD

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
Mark Stachiew

Mark Stachiew

Expert on YYZ

Mark Stachiew has been exploring the world and writing about it for more than 30 years. His travel stories have appeared in numerous newspapers, magazines and online publications in Canada, the United States and beyond.

Read more

Good to know

Low seasonJanuary
Cheapest flightC$ 116
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Chicago O'Hare Airport to Toronto Pearson Airport

When to book flights from Chicago to Pearson Intl

Are your dates flexible? Find out the best times to travel from Chicago to Pearson Intl 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.

FAQs for booking Chicago to Toronto flights

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

    In the last 3 days, the lowest price for a flight from Chicago to Toronto Pearson Intl Airport was C$ 116 for a one-way ticket and C$ 274 for a round-trip.

  • Which airports will I be using when flying from Chicago to Toronto?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Toronto (Toronto Pearson Intl). The cheapest flights are generally found on the Chicago O'Hare Airport to Toronto Pearson Intl flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Toronto?

    All the following airlines offer inflight Wi-Fi service on the Chicago to Toronto flight route: Air Canada, British Airways, Finnair, Iberia, American Airlines, and United Airlines.

  • Which aircraft models fly most regularly from Chicago to Toronto?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Toronto flight route.

  • Which airline alliances offer flights from Chicago to Toronto?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Toronto, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Toronto?

    There are direct flights from Chicago to Toronto on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to Toronto?

    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 Chicago to Toronto.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Toronto?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Toronto?

    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 Toronto with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Toronto?

    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 Toronto from Chicago 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 Chicago to Toronto Pearson Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 218 or less one-way and C$ 114 or less round-trip.

Prefer to fly direct from Chicago to Toronto?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Toronto Pearson Intl.
Find which airlines fly direct from Chicago to Toronto Pearson Intl Airport, which days they fly and book direct flights.

Direct departures

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 nonstop flights

Direct returns

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 nonstop flights

Reviews of the top airline flying from Chicago to Pearson Intl

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Toronto. 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 Chicago to Pearson Intl? 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 9269 reviews
7.1Entertainment
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
Airline reviews

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

6.0 Goodrob, Feb 2026
IAD - YYZ
Read more United Airlines reviews

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

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

Information on your arrival and departure airports

Pearson Intl (YYZ)