CHI - YYZ

C$ 75 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 8/7. 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 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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Cheap Flight Deals from Chicago to Toronto (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 Toronto 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 Chicago to Pearson Intl

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Pearson Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Air Canada Logo
8:25 p.m. - 11:07 p.m.ORD-YYZ
1h 42mdirect
Air Canada Logo
2:10 p.m. - 3:05 p.m.YYZ-ORD
1h 55mdirect
C$ 221Air Canada
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Air Canada Logo
10:40 a.m. - 5:28 p.m.ORD-YYZ
5h 48m1 stop
Air Canada Logo
12:00 p.m. - 12:55 p.m.YYZ-ORD
1h 55mdirect
C$ 225Air Canada
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Air Canada Logo
10:40 a.m. - 5:28 p.m.ORD-YYZ
5h 48m1 stop
Air Canada Logo
12:00 p.m. - 12:55 p.m.YYZ-ORD
1h 55mdirect
C$ 227Air Canada
Find Deal
Sat, 7 Jun - Sat, 14 Jun
 Logo
9:35 a.m. - 12:15 p.m.ORD-YYZ
1h 40mdirect
 Logo
3:00 p.m. - 8:12 p.m.YYZ-ORD
6h 12m1 stop
C$ 235
Find Deal
Sat, 17 May - Sat, 17 May
United Airlines Logo
7:04 a.m. - 9:58 a.m.ORD-YYZ
1h 54mdirect
United Airlines Logo
1:00 p.m. - 2:01 p.m.YYZ-ORD
2h 01mdirect
C$ 238United Airlines
Find Deal
Thu, 5 Jun - Mon, 9 Jun
United Airlines Logo
9:14 p.m. - 11:58 p.m.ORD-YYZ
1h 44mdirect
United Airlines Logo
7:00 a.m. - 7:59 a.m.YYZ-ORD
1h 59mdirect
C$ 239United Airlines
Find Deal
Fri, 6 Jun - Tue, 10 Jun
 Logo
9:31 p.m. - 11:51 a.m.ORD-YYZ
13h 20m1 stop
 Logo
2:45 p.m. - 3:50 p.m.YYZ-ORD
2h 05mdirect
C$ 242
Find Deal
Sat, 28 Jun - Sun, 29 Jun
Lufthansa Logo
1:00 p.m. - 3:46 p.m.ORD-YYZ
1h 46mdirect
Lufthansa Logo
12:00 p.m. - 12:55 p.m.YYZ-ORD
1h 55mdirect
C$ 288Lufthansa
Find Deal
Thu, 15 May - Sun, 18 May
Delta Logo
6:24 a.m. - 11:40 a.m.ORD-YYZ
4h 16m1 stop
Delta Logo
3:31 p.m. - 8:27 p.m.YYZ-ORD
5h 56m1 stop
C$ 322Delta
Find Deal
Fri, 6 Jun - Fri, 13 Jun
Delta Logo
6:25 p.m. - 10:58 p.m.MDW-YYZ
3h 33m1 stop
Delta Logo
10:11 a.m. - 12:29 p.m.YYZ-MDW
3h 18m1 stop
C$ 322Delta
Find Deal
Wed, 4 Jun - Wed, 11 Jun

Expert advice for your flight from Chicago to Pearson Intl

 
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 specific 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
American Airlines

American's Main Cabin Extra offers early boarding and complimentary drinks, enhancing travel comfort.


American Airlines' Wi-Fi offers 20 minutes free with an ad, useful for quick tasks.

Air Canada

Air Canada's Preferred Economy seats offer 4 extra inches of legroom for added comfort.


Air Canada provides free messaging for Aeroplan members on flights with Wi-Fi.

Read more about Air Canadaby Stefanie Waldek
United Airlines

United offers Priority Boarding to avoid gate-checking carry-ons, ideal for quick boarding.


United's Economy Plus offers up to 6 inches more legroom, enhancing comfort on short flights.

Airports
ORD

For a quick commute to downtown Chicago, take the CTA Blue Line train from ORD, which runs 24 hours and takes about 45 minutes.

Read more about ORDby Stefanie Waldek
YYZ

Use the UP Express train from YYZ to reach downtown Toronto in just 25 minutes, with trains running every 15 minutes.

Read more about YYZby Stefanie Waldek
Our travel experts
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
Stefanie Waldek

Stefanie Waldek

Expert on 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

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.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Toronto Pearson Intl Airport.
Our data shows that the cheapest route for a return flight from Chicago to Toronto Pearson Intl Airport cost C$ 142 and was between Chicago O'Hare Intl Airport (ORD) and Toronto Pearson Intl Airport (YYZ). On average, the best prices are found if you fly this route. The average price for a return flight for this route is C$ 142.

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 Tuesday and avoid Sundays 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 October, where tickets cost C$ 384 (return) on average. On the other hand, the most expensive months are November and April, where the average cost of round-trip tickets is C$ 500 and C$ 478 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.
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 C$ 178 on average.

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. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 75
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 11% 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$ 54 for a one-way ticket and C$ 160 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?

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

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

    The Boeing 777-300ER 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.

  • Which is the best airline for flights from Chicago to Toronto, United Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Chicago to Toronto are United Airlines and Air Canada. With an average price for the route of C$ 470 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 C$ 432 and an overall rating of 7.0.

  • 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.

See more FAQs

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$ 161 or less one-way and C$ 210 or less round-trip.

Prefer to fly direct from Chicago to Toronto?

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
See more nonstop flights

Top airlines 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 8683 reviews
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
7.1Entertainment
Airline reviews

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

10.0 ExcellentDr. Joseph, Apr 2025ORD - IAH
Read more United Airlines reviews

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

Terrible experience, flight was delayed both ways. Limited compensation for the 5+ hour delay. Will not be flying Air Canada Rouge, and don’t recommend you do either.

The boarding was relatively quick, the crew welcoming and flight uneventful. The omission of meals on all airlines is unacceptable especially when the flight is during a mealtime such as this one, (lunchtime), is unacceptable.

No Charging ports for personal electronics, which were required to use wifi entertainment.

Rushed, the boarding was a great deal like a Chinese fire drill.

it was red eye flight, it was ok, there was beverage service, thats it i didnt care much as i wanted to sleep

Everything went smoothly. I appreciate the selection of free movies.

I like the friendliness of the crew members. I think the snack could’ve been better instead of a small package of pretzel. I like that they offer me something to drink.

The TSA agents in Phoenix were incredibly rude and confiscated belongings that we wanted to check. The flight got changed without our knowledge to a worse situation. The whole thing was terrible

My experience with Air Canada was good. Great customer service… only a few delays and issues with the tunnel to exit the plain. I did not appreciate that we arrived at terminal D and had to go to terminal E to get the bags/ luggage.

They announced before boarding that the flight was full and there would be limited space in the overhead bins and you could check in for free. We did and after we boarded the plane found it was not full and there was plenty of space in the overhead bins. I’m not sure why they made this announcement.

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

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