YYZ - ORD

£79 Find Cheap Flights from Toronto to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 14/9. 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

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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Flights Deals

Cheap Flights from Toronto to Chicago (YYZ-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Toronto to Chicago 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 return flight deals from Toronto to Chicago

Fri, 19 Sep - Mon, 22 Sep
United Airlines Logo
07:00 - 07:59YYZ-ORD
1h 59mdirect
United Airlines Logo
21:31 - 10:04ORD-YYZ
11h 33m1 stop
£116United Airlines
Find Deal
Thu, 30 Oct - Sun, 2 Nov
United Airlines Logo
08:55 - 10:00YYZ-ORD
2h 05mdirect
United Airlines Logo
21:20 - 23:59ORD-YYZ
1h 39mdirect
£122United Airlines
Find Deal
Tue, 30 Sep - Thu, 2 Oct
American Airlines Logo
15:45 - 20:27YYZ-ORD
5h 42m1 stop
American Airlines Logo
09:48 - 17:15ORD-YYZ
6h 27m1 stop
£141American Airlines
Find Deal
Tue, 30 Sep - Thu, 2 Oct
American Airlines Logo
13:15 - 14:10YYZ-ORD
1h 55mdirect
American Airlines Logo
09:48 - 17:15ORD-YYZ
6h 27m1 stop
£150American Airlines
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Sat, 20 Sep - Tue, 23 Sep
Delta Logo
12:15 - 16:34YYZ-ORD
5h 19m1 stop
Delta Logo
17:45 - 22:58ORD-YYZ
4h 13m1 stop
£157Delta
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Fri, 4 Jul - Sun, 6 Jul
Delta Logo
17:04 - 22:21YYZ-ORD
6h 17m1 stop
Delta Logo
09:00 - 17:15ORD-YYZ
7h 15m1 stop
£161Delta
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Fri, 19 Sep - Sun, 21 Sep
Logo
12:45 - 18:29YYZ-ORD
6h 44m1 stop
Logo
13:55 - 20:58ORD-YYZ
6h 03m1 stop
£180
Find Deal
Fri, 25 Jul - Fri, 1 Aug
Logo
16:00 - 21:30YYZ-ORD
6h 30m1 stop
Logo
18:20 - 21:04ORD-YYZ
1h 44mdirect
£183
Find Deal
Thu, 31 Jul - Fri, 1 Aug
Air Canada Logo
06:15 - 11:24YYZ-ORD
6h 09m1 stop
Air Canada Logo
18:20 - 21:04ORD-YYZ
1h 44mdirect
£188Air Canada
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Sat, 19 Jul - Fri, 25 Jul
Air Canada Logo
00:30 - 07:55YYZ-ORD
8h 25m1 stop
Air Canada Logo
21:14 - 23:58ORD-YYZ
1h 44mdirect
£270Air Canada
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Expert advice

Expert advice for your flight from Toronto to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation 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
American Airlines

Basic Economy offers late boarding and no free checked bags, ideal for light travelers.


Main Cabin Extra provides early boarding and complimentary drinks, enhancing short flight comfort.

Read more about American Airlinesby Harriet Baskas
United Airlines

Economy Plus offers extra legroom, ideal for added comfort on short flights.


Priority Boarding places you in Zone 2, ensuring cabin bag space.

Read more about United Airlinesby Stefanie Waldek
British Airways

Economy fares include a cabin bag, avoiding surprise fees common with budget carriers.


BA's professional cabin crew enhance the overall flight experience.

Read more about British Airwaysby Duncan Madden
Air Canada

Preferred Economy seats offer extra legroom for a fee, enhancing comfort on short-haul flights.


Priority check-in available for higher fare classes, streamlining the airport experience.

Read more about Air Canadaby Stefanie Waldek
Airports
YYZ

Pearson's security queues can be long. Arrive early: 2 hours for domestic, 3 for international. Check wait times online.

Read more about YYZby Stefanie Waldek
ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby 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, 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 United Airlines, Air Canada, 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 out at sea, likely en route to Antarctica or the Arctic.

Read more
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan Madden

Duncan Madden

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Read more
Useful Info

KAYAK's insights & trends for Toronto to Chicago flights

Get data-powered insights and trends into flights from Toronto to Chicago 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 to Chicago?

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 on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Friday and avoiding Tuesdays 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 April, where tickets cost £186 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is £260 and £245 respectively.

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 12 weeks before departure.

Find deals

Good to know - Cheap tickets from Toronto to Chicago

Low seasonJanuary
High seasonAugust
Cheapest flight£79
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly (5% more expensive on average)
Flight from Toronto to Chicago

When to book flights from Toronto to Chicago

Are your dates flexible? Find out the best times to travel from Toronto to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns 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 Toronto to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travellers who flew the route from Toronto to Chicago 
Learn how KAYAK collects reviews and tips from users.
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.
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

FAQs for booking Toronto to Chicago 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 £108 for a one-way ticket and £157 for a return.

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

    Toronto airport is called Toronto Pearson Intl and the only airport in Chicago is Chicago O'Hare Intl.

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

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

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

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

  • Which airline alliances offer flights from Toronto to Chicago?

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

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

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

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

    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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto 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 to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Toronto with another airline.

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

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

  • Looking for a cheap flight from Chicago to Toronto? 25% of our users found flights on this route for £125 or less one-way and £163 or less round-trip.

Prefer to fly direct from Toronto to Chicago?

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 airline flying from Toronto to Chicago

 
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 Toronto to Chicago? 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.
7.1
Air CanadaOverall score based on 9531 reviews
6.3Food
7.0Comfort
6.8Entertainment
7.3Boarding
7.8Crew
Airline reviews

Somebody either kayak or Air Canada booked my flight under my preferred name Betty instead of my legal name and I almost was denied boarding my flight

2.0 MediocreAnonymous, May 2025YYZ - LAX
Read more Air Canada reviews

Somebody either kayak or Air Canada booked my flight under my preferred name Betty instead of my legal name and I almost was denied boarding my flight

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

The ground staff was so rude in Toronto airport ...very rude and did not answer simple questions, and made me look like a fool. Very rude ground staff.

My flight got delayed 5 times and then got cancelled eventually, I had to get a hotel and uber and pay for food for an extra night without any plans. It was a horrible experience, instead of Air Canada, I was flying with United .

I had a nice flight with free wifi. So I was able to message family members and stream music during my flight, which made the trip go by fast. I also enjoyed flying on there Airbus A220. The plane looked very new and it also got up to speed fast down the runway and didn't need much runway to get airborne.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Overall good experience. The flight from Toronto to Denver does not have entertainment - movies to watch.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

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

Everything you need to know for your flight from Toronto to Chicago

Information on your arrival and departure airports

Toronto (YYZ)
O'Hare Intl (ORD)

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