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YYZ - ORD

£124 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 27/8. 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
0 bags
Tue 2/7
Tue 9/7

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days, travellers have searched 41,909,192 times on KAYAK, and here's why:

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Cheap flight deals from Toronto to Chicago (YYZ-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 and deals for you by selecting your travel dates.
Choose your dates
13:00 - 14:02YYZ-ORD
2h 02mdirect
07:10 - 09:58ORD-YYZ
1h 48mdirect
£206Air Canada
Find Deal
Wed, 26 Jun - Mon, 1 Jul
07:00 - 07:57YYZ-ORD
1h 57mdirect
06:00 - 08:48ORD-YYZ
1h 48mdirect
£209United Airlines
Find Deal
Thu, 15 Aug - Sun, 18 Aug
18:00 - 23:17YYZ-ORD
6h 17m1 stop
06:00 - 08:48ORD-YYZ
1h 48mdirect
£213
Find Deal
Fri, 16 Aug - Sun, 18 Aug
07:55 - 08:51YYZ-ORD
1h 56mdirect
18:30 - 08:16ORD-YYZ
12h 46m1 stop
£217
Find Deal
Sat, 22 Jun - Mon, 24 Jun
12:30 - 18:24YYZ-ORD
6h 54m1 stop
13:31 - 22:53ORD-YYZ
8h 22m1 stop
£220Delta
Find Deal
Thu, 11 Jul - Tue, 23 Jul
12:30 - 18:24YYZ-ORD
6h 54m1 stop
17:15 - 23:12ORD-YYZ
4h 57m1 stop
£221Delta
Find Deal
Thu, 15 Aug - Sat, 17 Aug
20:00 - 19:48YYZ-ORD
24h 48m2 stops
06:00 - 22:29ORD-YYZ
15h 29m2 stops
£271WestJet
Find Deal
Fri, 30 Aug - Mon, 2 Sep
07:45 - 14:32YYZ-ORD
7h 47m1 stop
06:00 - 12:10ORD-YYZ
5h 10m1 stop
£290WestJet
Find Deal
Thu, 15 Aug - Sun, 18 Aug
13:29 - 04:40YYZ-ORD
16h 11m2 stops
21:22 - 14:30ORD-YYZ
16h 08m1 stop
£739Alaska Airlines
Find Deal
Thu, 15 Aug - Sun, 18 Aug
06:55 - 04:40YYZ-ORD
22h 45m2 stops
21:22 - 14:30ORD-YYZ
16h 08m1 stop
£787Alaska Airlines
Find Deal
Thu, 15 Aug - Sun, 18 Aug

Flights from Toronto to Chicago - Travel Insights & Trends

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 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 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 January, where tickets cost £206 on average. On the other hand, the most expensive months are August and July, where the average cost of tickets is £318 and £304 respectively.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 39 days before departure.

Which airlines provide the cheapest flights from Toronto to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Toronto to Chicago found by KAYAK users in the last 72 hours was for £206 on Air Canada, followed by United Airlines (£209). One-way flight deals have also been found from as low as £124 on Air Canada and from £135 on Delta.

Which airlines fly most frequently between Toronto and Chicago?

United Airlines (11 flights per day), American Airlines (5 flights per day), and Air Canada (4 flights per day) are the most frequent flyers of this route.

Which airlines fly direct between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.
There are 3 airlines that fly direct from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. They are: Air Canada, American Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Air Canada at £190 for a one-way flight. On average, the best prices for this route can be found at Air Canada.

How many flights are there between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport per day?

Each day, there are between 17 and 22 nonstop flights that take off from Toronto Pearson Intl Airport and land in Chicago O'Hare Intl Airport, with an average flight time of 1h 57m. The most common departure time is 07:00 and most flights take off in the morning. Each week, there are 142 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Toronto to Chicago take?

Direct flights cover the 436 miles separating Toronto and Chicago in about 1h 56m.

What’s the earliest departure time from Toronto to Chicago?

Early birds can take the earliest flight from Toronto Pearson Intl Airport at 06:30 and will be landing in Chicago O'Hare Intl Airport at 07:25.

What’s the latest departure time from Toronto to Chicago?

If you prefer to fly at night, the latest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport jets off at 21:00 and lands at 22:02.

Good to know - Cheap tickets from Toronto to Chicago

Low season

January

High season

August

Cheapest flight

£124
Best time to beat the crowds (9% less expensive on average)
Most popular time to fly (20% 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.

FAQs for booking Toronto to Chicago 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 £158 for a one-way ticket and £263 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, American Airlines, and United Airlines offer inflight Wi-Fi service on the Toronto to Chicago flight route.

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

    The Boeing 737 MAX 8 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.

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 from Chicago to Toronto? 25% of our users found flights on this route for £127 or less one-way and £398 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

Flights from Toronto to Chicago: the best tips from KAYAK users

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

Prefer to fly direct from Toronto to Chicago?

Find which airlines fly direct from Pearson Intl to O'Hare Intl, 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, +11 more

ANA, Air Canada, +12 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, +11 more

ANA, Air Canada, +12 more

Friday

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

ANA, Air Canada, +13 more

Saturday

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

ANA, Air Canada, +14 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, +13 more

ANA, Air Canada, +14 more

Wednesday

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

ANA, Air Canada, +14 more

Thursday

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

ANA, Air Canada, +13 more

Friday

ANA, Air Canada, Air New Zealand, +14 more

ANA, Air Canada, +15 more

Saturday

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

ANA, Air Canada, +14 more

Sunday

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

ANA, Air Canada, +14 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.
7.0
Air CanadaOverall score based on 7021 reviews
7.8Crew
7.0Comfort
7.2Boarding
6.8Entertainment
6.2Food
Airline reviews

Seating for almost 3 hours in the plan before aircraft takeoff. Very exhausted .

2.0 MediocreAnonymous, Jun 2024YYZ - SFO
Read more about Air Canada reviews

Seating for almost 3 hours in the plan before aircraft takeoff. Very exhausted .

The bathroom did not have hand soap. That is unacceptable.

I was seated next to someone who was, to be polite, not a small person. I had to press myself against the wall as I had no personal space. Aside from that the crew was wonderful and they got me home safely, which is the most important part of my journey. I am very appreciative to your air crews for the job they have, which isn't easy, and appreciative of the fact that they are professional and courteous. The employees I encountered on my journey, with the few exceptions I mentioned in a previous review, are a credit to Air Canada.

Air Canada had a lot of delays on our flight going back to Seattle. So much inconvenience for a long trip.

The Carry-on luggage that approved by TSA and all other airlines,- always an issue with Air Canada. This is inappropriate as my carry on suitcase meets the requirements however it always asked to check in on AC flight on the gate. Yes I have it for free, but it takes extra time to pick up on the carousel. Apparently it fit the overhead space, so why AC has this issue all the time?

The terminal this flight boarded from was so far away, poorly temperature controlled, and generally uncomfortable. The plane was small but the flight was short, so it wasn't so bad.

Seriously need to improve the time schedule and the plans

Great TV, easy boarding, wonderful ground crew and flight crew.

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

Book cheap flights from Toronto to Chicago

Cheapest flights to Chicago from Toronto found in 2024

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
27/8Tue
1 stopAir Canada
4h 31mYYZ-ORD
£124
25/6Tue
1 stopDelta
8h 09mYYZ-ORD
£135
20/8Tue
1 stopDelta
13h 45mYYZ-ORD
£145
28/7Sun
1 stopUnited Airlines
13h 40mYYZ-ORD
£148
24/6Mon
1 stopUnited Airlines
15h 02mYYZ-ORD
£149
24/6Mon
2 stopsWestJet
10h 58mYYZ-ORD
£153
14/7Sun
1 stopUnited Airlines
10h 30mYYZ-ORD
£159
8/6Sat
directAir Canada
1h 54mYYZ-ORD
£163
8/6Sat
2 stops
18h 44mYYZ-ORD
£166
5/8Mon
1 stopWestJet
19h 51mYYZ-ORD
£167

Search by stops

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Last minute flights from Toronto to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
7/6Fri
directUnited Airlines
2h 02mYYZ-ORD
12/6Wed
multi-stopUnited Airlines
5h 37mORD-YYZ
£386
5/6Wed
direct
2h 02mYYZ-ORD
9/6Sun
multi-stop
12h 51mORD-YYZ
£388
7/6Fri
multi-stopUnited Airlines
5h 55mYYZ-ORD
14/6Fri
directUnited Airlines
1h 43mORD-YYZ
£391
6/6Thu
multi-stopWestJet
5h 19mYYZ-ORD
9/6Sun
multi-stopWestJet
12h 20mORD-YYZ
£394
7/6Fri
direct
1h 57mYYZ-ORD
12/6Wed
multi-stop
12h 51mORD-YYZ
£395
5/6Wed
multi-stopWestJet
5h 03mYYZ-ORD
9/6Sun
multi-stopWestJet
12h 20mORD-YYZ
£400
7/6Fri
multi-stopDelta
4h 17mYYZ-ORD
10/6Mon
multi-stopDelta
8h 25mORD-YYZ
£406
3/6Mon
multi-stopDelta
8h 22mYYZ-ORD
6/6Thu
multi-stopDelta
4h 32mORD-YYZ
£476
4/6Tue
multi-stopAeromexico
20h 17mYYZ-ORD
6/6Thu
multi-stopAeromexico
20h 39mORD-YYZ
£1,308
3/6Mon
multi-stopAeromexico
14h 57mYYZ-ORD
5/6Wed
multi-stopAeromexico
20h 39mORD-YYZ
£1,359

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Toronto - Chicago Flights

Departure:

Toronto (YYZ)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Toronto

Cabin classes:

£6,682
£862
£1,168
£192

Browse origins:

  • Flights » 
  • Toronto Pearson Airport

Browse destinations:

  • Flights » 
  • Worldwide » 
  • Chicago O'Hare Airport