CHI - YYZ

C$ 114 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 24/2. 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 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
C$ 257
Overall average: C$ 417
Multiple Airlines
Thu 22/1Thu 29/1
ORD - YYZ • 1 stop
Cheapest direct flights
C$ 273
Typical prices: C$ 387-C$ 613
Air Canada
Fri 6/2Mon 9/2
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
United Airlines
Cheapest • from C$ 312 (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
5 weeks
in advance
Our data shows that travellers who book at least 5 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

Thu, 22 Jan - Thu, 29 Jan
Multiple Airlines Logo
7:20 a.m. - 11:20 p.m.
ORD
-
YYZ
15h 00m1 stop
Multiple Airlines Logo
1:30 p.m. - 8:29 p.m.
YYZ
-
ORD
31h 59m2 stops
C$ 257Multiple Airlines
Fri, 23 Jan - Mon, 26 Jan
Multiple Airlines Logo
5:15 a.m. - 2:40 p.m.
ORD
-
YYZ
8h 25m1 stop
Multiple Airlines Logo
3:40 p.m. - 11:22 a.m.
YYZ
-
ORD
20h 42m1 stop
C$ 261Multiple Airlines
Wed, 21 Jan - Wed, 28 Jan
Multiple Airlines Logo
7:20 a.m. - 11:20 p.m.
ORD
-
YYZ
15h 00m1 stop
Multiple Airlines Logo
3:40 p.m. - 11:46 p.m.
YYZ
-
ORD
9h 06m1 stop
C$ 264Multiple Airlines
Thu, 22 Jan - Tue, 27 Jan
Multiple Airlines Logo
7:20 a.m. - 11:20 p.m.
ORD
-
YYZ
15h 00m1 stop
Multiple Airlines Logo
3:40 p.m. - 11:46 p.m.
YYZ
-
ORD
9h 06m1 stop
C$ 265Multiple Airlines
Thu, 22 Jan - Thu, 29 Jan
Multiple Airlines Logo
7:20 a.m. - 11:20 p.m.
ORD
-
YYZ
15h 00m1 stop
Multiple Airlines Logo
8:00 p.m. - 8:29 p.m.
YYZ
-
ORD
25h 29m1 stop
C$ 267Multiple Airlines
Fri, 6 Feb - Mon, 9 Feb
Air Canada Logo
2:00 p.m. - 4:39 p.m.
ORD
-
YYZ
1h 39mdirect
Air Canada Logo
12:05 p.m. - 1:01 p.m.
YYZ
-
ORD
1h 56mdirect
C$ 273Air Canada
Fri, 23 Jan - Tue, 27 Jan
Multiple Airlines Logo
5:15 a.m. - 2:40 p.m.
ORD
-
YYZ
8h 25m1 stop
Multiple Airlines Logo
7:10 a.m. - 10:04 p.m.
YYZ
-
ORD
15h 54m1 stop
C$ 276Multiple Airlines
Thu, 5 Feb - Wed, 11 Feb
Delta Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
C$ 320Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
9:53 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 06m1 stop
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
C$ 331Delta
Thu, 5 Feb - Sun, 8 Feb
KLM Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
KLM Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
C$ 342KLM
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 January.

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$ 158 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$ 330 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is C$ 487 and C$ 458 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$ 400, 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 5 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.

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.
Airlines
American Airlines

Main Cabin Extra offers early boarding and complimentary drinks for a fee.


Basic Economy includes late boarding and no free checked bags.

Air Canada

Priority check-in available for higher fare classes and elite status members.


Economy seats offer 76-86 cm legroom; Preferred Economy adds 10 cm for a fee.

Airports
ORD

For a quick trip to downtown Chicago, take the CTA Blue Line from ORD, which runs 24/7 and takes about 45 minutes.

YYZ

Use the Union Pearson Express for a stress-free 25-minute ride from YYZ to downtown Toronto, with trains every 15 minutes.

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 and ORD

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
Mark Stachiew

Mark Stachiew

Expert on YYZ

Mark Stachiew

Mark Stachiew

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$ 114
Best time to beat the crowds but there is an average 10% 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$ 114 for a one-way ticket and C$ 257 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, American Airlines, British Airways, Iberia, United Airlines, Finnair, and Porter 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.

  • 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$ 363 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$ 361 and an overall rating of 7.1.

  • 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$ 183 or less one-way and C$ 282 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 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 9115 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

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

2.0 Mediocrejbritto, Dec 2025
ORD - YYZ
Read more United Airlines reviews

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.

I liked the snacks and the flight attendants were friendly.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

Elderly female flight attendant was not customer friendly. There were only about 12 people on a regional jet that had about 60 seats. There were 8 exit row seats and none of them were taken. We attempted to sit in those seats and the flight attendant gave the standard " you didn't pay for those" so she would not allow us to move. What harm would that have caused ? They assigned seats to 5 of the 12 people in 2 rows, row 20 and 21. A simple friendly customer experience gesture of allowing us to sit in exit rows would have gone a long way in me having a very favorable impression on Air Canada. After that I have very poor impression of Air Canada and will not fly with them when I can avoid it.

Pearson Airport could not properly handle all the passengers who they needed to process in order to properly get them on board. As a result, I missed the departure of my flight from Toronto. The only saving grace is that Air Canada found a flight that only delayed me by one hour. However, this was no thanks to Pearson Airport!

Almost everything it was a “cool” ambiance but we arrived to Toronto so that it’s ok for me

The crew was really nice. The plane seats were kinda small even for a 5’6” / 158 lbs person.

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

Information on your arrival and departure airports