YYZ - ORD

C$ 173 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 5/7. 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.
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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 Flight Deals from Pearson Intl to O'Hare Intl (YYZ-ORD)

 
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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Pearson Intl to O'Hare Intl.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 343American Airlines
Find Deal
Sat, 1 Mar - Wed, 5 Mar
1:15 p.m. - 2:10 p.m.YYZ-ORD
1h 55mdirect
8:10 a.m. - 10:50 a.m.ORD-YYZ
1h 40mdirect
C$ 348American Airlines
Find Deal
Thu, 10 Apr - Sat, 12 Apr
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
8:30 p.m. - 11:11 p.m.ORD-YYZ
1h 41mdirect
C$ 351Air Canada
Find Deal
Sun, 16 Feb - Sun, 23 Feb
9:00 p.m. - 10:06 p.m.YYZ-ORD
2h 06mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 354Air Canada
Find Deal
Thu, 13 Feb - Thu, 20 Feb
6:40 p.m. - 7:37 p.m.YYZ-ORD
1h 57mdirect
9:50 a.m. - 12:25 p.m.ORD-YYZ
1h 35mdirect
C$ 356
Find Deal
Wed, 12 Feb - Sat, 22 Feb
3:50 p.m. - 10:40 a.m.YYZ-ORD
19h 50m2 stops
2:29 p.m. - 12:12 a.m.ORD-YYZ
8h 43m1 stop
C$ 371
Find Deal
Tue, 18 Feb - Tue, 25 Feb
6:30 a.m. - 11:30 a.m.YYZ-ORD
6h 00m1 stop
6:15 a.m. - 1:44 p.m.ORD-YYZ
6h 29m1 stop
C$ 406WestJet
Find Deal
Thu, 13 Feb - Mon, 17 Feb
9:00 a.m. - 10:04 a.m.YYZ-ORD
2h 04mdirect
1:04 p.m. - 3:45 p.m.ORD-YYZ
1h 41mdirect
C$ 426United Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
6:52 a.m. - 8:01 a.m.YYZ-ORD
2h 09mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 439United Airlines
Find Deal
Fri, 14 Feb - Sun, 16 Feb
5:05 p.m. - 10:36 p.m.YYZ-ORD
6h 31m1 stop
9:34 a.m. - 11:30 p.m.ORD-YYZ
12h 56m2 stops
C$ 459WestJet
Find Deal
Fri, 21 Feb - Sun, 9 Mar

Flights from Pearson Intl to O'Hare Intl - Travel Insights & Trends

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.
If your flying dates are flexible, you should consider flying to Chicago O'Hare Airport on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Toronto Pearson Airport to Chicago O'Hare Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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 February, where tickets cost C$ 403 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is C$ 515 and C$ 479 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.
No, with an average price for the route of C$ 539, prices are generally cheapest when you fly direct.

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 18 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 173
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly (2% more expensive on average)
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 travellers 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

  • Are there alternative arrival airports to Chicago O'Hare International Airport (ORD)?

    You can also find flights from Toronto Pearson International Airport (YYZ) that land at Chicago Midway International Airport (MDW), an alternative to ORD. MDW may be better if you will stay in Chicago's south or west sides. However, this route has limited flight options and is mainly served by one-stop flights operated by WestJet and Delta Air Lnes.

  • How do I get to downtown Chicago from Chicago O'Hare International Airport (ORD)?

    ORD is around 29 km from downtown Chicago. If you have less luggage, consider the CTA Blue Line L-train, which takes you to downtown Chicago in 30 to 40 minutes. PACE buses, through their Route 250 and Route 330 lines, take you to different parts of downtown Chicago from ORD. Taxis, ridesharing options, and various car rental providers with a counter at the airport are other options.

  • What lounges are available at Toronto Pearson International Airport (YYZ)?

    You can check into the Air Canada Maple Leaf Lounge, Plaza Premium Lounge, American Airlines Admirals Club (proof of American Airlines ticket required), or Air France KLM Lounge. These lounges have comfortable sofas, free WiFi, dining and entertainment options.

  • Which airlines have Business Class flights from Toronto Pearson Airport to Chicago O'Hare Airport?

    Consider booking Air Canada, United Airlines, and American Airlines, which fly Business Class on their direct and one-stop flights from Toronto Pearson Airport (YYZ) to Chicago O'Hare Airport (ORD). This travel option lets you enjoy priority check-in and boarding, access to specific lounges, specialized onboard service, gourmet dining options, in-flight entertainment, and a special baggage allowance.

  • 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 C$ 120 for a one-way ticket and C$ 238 for a round-trip.

  • 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 Boeing 737 MAX 8 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 direct 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 C$ 468 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 C$ 550 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 travellers 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.

  • 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 C$ 351 or less one-way and C$ 617 or less round-trip.
  • Toronto Pearson International Airport (YYZ) is the main hub for Canada’s national carrier Air Canada. It also serves other major airlines with domestic and international connections. Flights from Toronto Pearson Airport to Chicago O'Hare Airport (ORD) are mainly operated by Air Canada, United Airlines, ANA, American Airlines, British Airways, WestJet, and Delta Air Lines.
  • The YYZ to ORD route features many direct and one-stop flights. If you take a one-stop flight, you’ll likely have a layover in Ottawa (YOW), Detroit (DTW), Montreal (YUL), Atlanta (ATL), Washington (WAS), Minneapolis (MSP), New York (EWR), or Charlotte (CLT). The flight route determines the layover city since no airline has a specific layover airport.
  • Alternative Toronto airports with flights to Chicago O'Hare International Airport (ORD) include John C. Munro Hamilton International Airport (YHM), Region of Waterloo International Airport (YKF), and Billy Bishop Toronto City Airport (YTZ). These airports only have one-stop flights to ORD. YYZ remains the best departure airport because it has more flight options to ORD.
  • If you wish to extend your trip from ORD, you can fly to domestic destinations such as Atlanta, Dallas, New York, Los Angeles, and San Francisco or international destinations like London, Mexico, Tokyo, Frankfurt, and different Caribbean cities.
  • For eco-friendly flights from Toronto Pearson Airport to Chicago O'Hare Airport, consider booking United Airlines flights which emit 38% less CO₂ (117 kg CO₂) per passenger compared to other flights on this route. You may also consider Air Canada flights which emit 29% less CO₂ (135 kg CO₂).
See more tips

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, +13 more

ANA,Air Canada, +14 more

Tuesday

ANA,Air Canada,Air New Zealand, +11 more

ANA,Air Canada, +12 more

Wednesday

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

ANA,Air Canada, +13 more

Thursday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 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, +13 more

ANA,Air Canada, +14 more

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Toronto Pearson Intl

Monday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Tuesday

ANA,Air Canada,Air New Zealand, +9 more

ANA,Air Canada, +10 more

Wednesday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Thursday

ANA,Air Canada,Air New Zealand, +9 more

ANA,Air Canada, +10 more

Friday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Saturday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

Sunday

ANA,Air Canada,Air New Zealand, +10 more

ANA,Air Canada, +11 more

See more nonstop flights
See more nonstop flights

Top 5 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.
7.9
Porter AirlinesOverall score based on 277 reviews
7.6Food
6.9Entertainment
8.2Boarding
8.0Comfort
8.7Crew
Airline reviews

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

8.0 ExcellentJason, Dec 2024YUL - YHZ
Read more Porter Airlines reviews

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

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.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

Cramped seats. Audio jack for the in -flight entertainment was broken.

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.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

Fantastic. I am low vision and was impressed with how helpful and accommodating the service tam was. It was super appreciated! I was pleasantly surprised about how delicious the food was. Like, “I wish I had more even though I’m no longer hungry” delicious. 100% enjoyable trip.

Very good over all , would have been nice to have entertainment on the flight

Absolutely the worst airline I have ever taken. They lost my baggage and told me my bag tags had been cancelled. When my bags arrived days later I had to pick them up at 3:15 am. My return flight was delayed another 6 hours and they broke my bag. Westjet does nothing to try and make it a better customer experience and all the customers services representatives I spoke with were useless and incompetent. Never flying westjet again.

Easy self checkin and baggage drop. No in seat entertainment, but wifi and app worked well

it's all good nothing you can do make better 😌

Single flights to Cancun purchased through third-party, initially had issues printing luggage labels with the lady at the airport Pearson… Was super friendly and assisted quickly despite being very busy

The flight was on time and shorter time arrival than planned. I was an ultra basic passenger and understood one personal item on the plane. The announcements of one personal item and zone 9 boarding certainly felt like we were separated from the rest. Actually zone 9 passengers should be boarded second; we are not blocking aisles and can be seated much faster and deboarded faster too.

Still sitting in a hotel when I'm due for work

Delays happen but communication and care were very low on what ended up being a long day.

Never been on a long haul flight that didn't have on flight entertainment. I hope the way back is better !

Very easy boarding. The on board snacks were not good.

So we didn't actually go. We were hoping to go for the Inauguration of the first female president. When That Guy got elected, we bailed. Unfortunately, we got basically none of our money back, despite having travel insurance. Would not fly with Air Canada again unless I had to.

flight was delayed, there was open communication about the delay the delay pushed way past the posted delay time and

Ok Did not like that the second leg of flight was moved earlier making it a rush to make it

This was my first time flying on Air Canada and the experience was good and pleasant enough, great crew members and the price I paid was amazing,

This was my first time and the experience was good and pleasant enough, great crew members and the price I paid was amazing,

I was overcharged either by United or sister airline Air Canada. It's exhausting dealing with companies nowadays that irresponsibly abuse access to credit/debit cards.

Air Canada is not only the worst airline in the business but the worst business in history.

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

I overpaid for the trip. They would not consider giving me any compensation or a credit.

Service was excellent, but they ran out of food options by the time they got to my seat (row 36).

Travelling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
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Schaumburg
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Hoffman Estates
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Gurnee
North Chicago
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Everything you need to know for your flight from Pearson Intl to O'Hare Intl

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