YYZ - ORD

$119 Find Cheap Flights from Toronto Pearson Airport to Chicago O'Hare Airport

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 O'Hare Intl departing on 5/17. 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 Chicago O'Hare Intl Airport

 
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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Cheap Flights from Pearson Intl to O'Hare Intl

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

Recent round-trip flight deals from Pearson Intl to O'Hare Intl

KAYAK's recommended round-trip deals from the most popular airlines that fly from Pearson Intl to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Air Canada Logo
9:00 pm - 10:05 pmYYZ-ORD
2h 05mnonstop
Air Canada Logo
8:25 pm - 11:07 pmORD-YYZ
1h 42mnonstop
$199Air Canada
Find Deal
Fri, Jun 13 - Sun, Jun 15
Air Canada Logo
4:30 pm - 5:24 pmYYZ-ORD
1h 54mnonstop
Air Canada Logo
8:25 pm - 11:07 pmORD-YYZ
1h 42mnonstop
$201Air Canada
Find Deal
Thu, Jun 5 - Wed, Jun 11
Delta Logo
6:00 am - 9:21 amYYZ-ORD
4h 21m1 stop
Delta Logo
10:30 am - 5:18 pmORD-YYZ
5h 48m1 stop
$224Delta
Find Deal
Thu, Apr 24 - Sun, Apr 27
United Airlines Logo
11:00 am - 12:03 pmYYZ-ORD
2h 03mnonstop
United Airlines Logo
6:30 pm - 9:16 pmORD-YYZ
1h 46mnonstop
$227United Airlines
Find Deal
Thu, May 15 - Fri, May 23
 Logo
7:47 pm - 11:30 pmYYZ-ORD
4h 43m1 stop
 Logo
7:04 am - 9:58 amORD-YYZ
1h 54mnonstop
Fri, Jun 13 - Sun, Jun 15
Delta Logo
6:00 am - 9:24 amYYZ-ORD
4h 24m1 stop
Delta Logo
6:45 am - 11:25 amORD-YYZ
3h 40m1 stop
$230Delta
Find Deal
Tue, Apr 22 - Tue, Apr 29
 Logo
12:00 pm - 12:54 pmYYZ-ORD
1h 54mnonstop
 Logo
6:30 pm - 9:16 pmORD-YYZ
1h 46mnonstop
Wed, May 7 - Fri, May 9
United Airlines Logo
7:47 pm - 11:15 pmYYZ-ORD
4h 28m1 stop
United Airlines Logo
8:25 pm - 11:07 pmORD-YYZ
1h 42mnonstop
$243United Airlines
Find Deal
Tue, May 13 - Wed, May 21
American Airlines Logo
6:20 pm - 7:15 pmYYZ-ORD
1h 55mnonstop
American Airlines Logo
6:00 am - 11:55 amORD-YYZ
4h 55m1 stop
$245American Airlines
Find Deal
Tue, Apr 29 - Thu, May 8
American Airlines Logo
5:55 pm - 11:08 pmYYZ-ORD
6h 13m1 stop
American Airlines Logo
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$249American Airlines
Find Deal
Sat, May 17 - Sun, May 18

Expert advice for your flight from Pearson Intl to O'Hare 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 original 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
Qatar Airways

Qatar's Economy includes a free checked bag, enhancing value for budget-conscious travelers.


Qatar's Wi-Fi may have blackout zones; set expectations accordingly for connectivity.

Air Canada

Air Canada's Preferred Economy offers up to four extra inches of legroom for added comfort.


Air Canada's Maple Leaf Lounges offer snacks and drinks, accessible with certain fare classes.

Read more about Air Canadaby Stefanie Waldek
American Airlines

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


American's Basic Economy is budget-friendly but restricts seat selection and boarding group.

United Airlines

United's Premier Access offers priority check-in and boarding, ideal for quick, efficient travel.


United's Economy Plus seats offer up to six inches more legroom for added comfort on short flights.

Airports
YYZ

Toronto Pearson's security lines can be long. Arrive at least two hours early for domestic flights and three for international. Check wait times on the airport's website.

Read more about YYZby Stefanie Waldek
ORD

Take the CTA Blue Line train from O'Hare to downtown Chicago. It runs 24/7 and takes about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Qatar Airways, 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
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

KAYAK's insights & trends for Pearson Intl to O'Hare Intl flights

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

What’s the cheapest day of the week to fly from Toronto Pearson Airport to Chicago O'Hare Airport?

The average price of all round-trip flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
For Toronto Pearson Airport to Chicago O'Hare Airport, Friday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago O'Hare Airport back to Toronto Pearson Airport, the best deals are generally found on Friday, with Sunday being the most expensive.

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

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 O'Hare 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 Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is April, where tickets cost $266 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $353 and $333 respectively.

Can I save money by flying with a layover from Toronto Pearson Intl Airport to Chicago O'Hare 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 $661 on average.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago O'Hare 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 Toronto Pearson Intl Airport to Chicago O'Hare 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 Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

$119
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

When to book flights from Pearson Intl to O'Hare Intl

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

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

Insights shared by verified travelers who flew the route from Pearson Intl to O'Hare Intl 
BrianFlew with Air CanadaOct 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.
Jo AnnFlew with Air CanadaJun 2024
It seemed that anyone who checked a bag was able to retrieve it quickly.
Verified travelerFlew with United AirlinesMar 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
Verified travelerFlew with Air CanadaFeb 2024
I would definitely choose Air Canada over dirty old United airplanes any day.
Verified travelerFlew with United AirlinesDec 2023
The departure time was very convenient with the United.

FAQs for booking Toronto Pearson Airport to Chicago O'Hare Airport flights

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

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport was $119 for a one-way ticket and $199 for a round-trip.

  • Do I need a passport to fly between Toronto Pearson Airport and Chicago O'Hare Airport?

    Yes, you’ll need a passport to travel to Chicago O'Hare Airport from Toronto Pearson Airport.

  • Which airlines offer Wi-Fi service onboard planes from Toronto Pearson Airport to Chicago O'Hare Airport?

    Air Canada, and United Airlines offer inflight Wi-Fi service on the Toronto Pearson Airport to Chicago O'Hare Airport flight route.

  • Which aircraft models fly most regularly from Toronto Pearson Airport to Chicago O'Hare Airport?

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto Pearson Airport to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Toronto Pearson Airport to Chicago O'Hare Airport?

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

  • On which days can I fly direct from Toronto Pearson Airport to Chicago O'Hare Airport?

    There are nonstop flights from Toronto Pearson Airport to Chicago O'Hare Airport 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 $308 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 $328 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Toronto Pearson Airport to Chicago O'Hare Airport?

    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 O'Hare Airport.

  • 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 O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport with an airline and back to Toronto Pearson Airport with another airline. Booking your flights between Toronto Pearson Airport and ORD can sometimes prove cheaper using this method.

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

    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 O'Hare Airport from Toronto Pearson Airport 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 Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $182 or less one-way and $276 or less round-trip.

Prefer to fly direct from Toronto Pearson Airport to Chicago O'Hare Airport?

Find which airlines fly direct from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Chicago O'Hare Intl

Monday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Tuesday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Wednesday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Thursday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Friday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Saturday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Sunday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Toronto Pearson Intl

Monday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Tuesday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Wednesday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Thursday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Friday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Saturday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Sunday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

See more direct flights
See more direct flights

Top 3 airlines serving from Pearson Intl to O'Hare Intl

 
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 O'Hare 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 8616 reviews
7.7Boarding
8.1Crew
7.0Entertainment
6.6Food
7.3Comfort
Airline reviews

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

2.0 MediocreJ.C., Mar 2025COS - ORD
Read more United Airlines reviews

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

Ensure prepaid food arrangements are appropriately understood by flight crew of who purchased and who did not

All was fine. Weather was a bit stormy, but nothing kayak can do about that! 😊

I paid for a comfort class seat and was seated in economy.

My plane was cancelled and had to be rebook for the evening was not happy.

The flight was cancelled and we had to rebook on Porter to make our cruise the next day. Air Canada has not compensated. We won’t be flying with them again. This is the second time this has happened. Also the return flight was delayed 2 hours who knows why.

Separated me and my wife and wife’s sister in far apart different seats even though I booked them all together. Just scams after scams to make us pay more. Worst airline

If you want your flight to get delayed constantly for 13+ hours and given a 10 dollar food voucher the. I would say take air canada. Worst experience ever.

My flight was cancelled and I was left to figure out where to find a hotel, something to eat and how to get a new flight at 11:30pm. Wasted a day. Thanks, Air Canada!

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

They kept changing the gate (6 times in 30 minutes) and then left us on the plane for 4 hours before departure. Likely was the storm, which is understandable, but the lack of communication and the e constant running between gates at opposite ends of the airport really threw me and my friend for a loop.

Everything you need to know for your flight from Pearson Intl to O'Hare Intl

Information on your arrival and departure airports

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