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Find cheap flights from Toronto to Chicago from £121

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 27/5. 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
Fri 24/5
Fri 31/5

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 45,119,101 times on KAYAK, and here's why:

Save 28% or moreCompare multiple travel sites with one search.

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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
12:30 - 16:33YYZ-ORD
5h 03m1 stop
06:00 - 11:38ORD-YYZ
4h 38m1 stop
£208Delta
Find Deal
Thu, 6 Jun - Wed, 12 Jun
06:30 - 14:59YYZ-ORD
9h 29m1 stop
13:25 - 22:50ORD-YYZ
8h 25m1 stop
£214Delta
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Thu, 27 Jun - Tue, 9 Jul
19:43 - 07:40YYZ-ORD
12h 57m1 stop
12:00 - 14:52ORD-YYZ
1h 52mdirect
£218United Airlines
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Fri, 31 May - Sun, 2 Jun
07:59 - 08:55YYZ-ORD
1h 56mdirect
16:00 - 18:48ORD-YYZ
1h 48mdirect
£221
Find Deal
Sat, 29 Jun - Sat, 6 Jul
08:10 - 09:06YYZ-ORD
1h 56mdirect
08:45 - 17:28ORD-YYZ
7h 43m1 stop
£223United Airlines
Find Deal
Thu, 15 Aug - Sun, 18 Aug
07:55 - 08:51YYZ-ORD
1h 56mdirect
06:00 - 08:45ORD-YYZ
1h 45mdirect
£239
Find Deal
Thu, 30 May - Wed, 5 Jun
07:45 - 14:36YYZ-ORD
7h 51m1 stop
17:45 - 22:50ORD-YYZ
4h 05m1 stop
£261WestJet
Find Deal
Sat, 3 Aug - Sat, 3 Aug
19:10 - 22:39YYZ-ORD
4h 29m1 stop
19:30 - 17:08ORD-YYZ
20h 38m1 stop
£265WestJet
Find Deal
Fri, 31 May - Fri, 7 Jun
00:30 - 08:00YYZ-ORD
8h 30m1 stop
07:10 - 09:58ORD-YYZ
1h 48mdirect
£290Air Canada
Find Deal
Wed, 22 May - Mon, 27 May
07:30 - 12:42YYZ-ORD
6h 12m1 stop
07:26 - 09:58ORD-YYZ
1h 32mdirect
£291Air Canada
Find Deal
Tue, 27 Aug - Fri, 30 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 £189 on average. On the other hand, the most expensive months are August and July, where the average cost of tickets is £351 and £327 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 80 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 £208 on Delta, followed by United Airlines (£218). One-way flight deals have also been found from as low as £121 on United Airlines and from £125 on Delta.

Which airlines fly most frequently between Toronto and Chicago?

American Airlines (9 flights per day), United Airlines (8 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 £195 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 21 and 25 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 13:00 and most flights take off in the morning. Each week, there are 163 flights. The most frequent day of departure is Sunday, 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 54m.

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 07:26.

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 22:04.

Good to know - Cheap tickets from Toronto to Chicago

Low season

January

High season

August

Cheapest flight

£121
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly (25% 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 £150 for a one-way ticket and £258 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

Top tips for finding a cheap flight from Toronto to Chicago

  • Looking for a cheap flight from Chicago to Toronto? 25% of our users found flights on this route for £231 or less one-way and £370 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 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, +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, +13 more

ANA, Air Canada, +14 more

Saturday

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

ANA, Air Canada, +15 more

Sunday

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

ANA, Air Canada, +14 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 6859 reviews
6.2food
7.2boarding
7.8crew
7.0comfort
6.8entertainment
Airline reviews

It was an excellent experience, traveling from Toronto to Denver with United.

10.0 ExcellentJoshua, Apr 2024YYZ - DEN
Read more about Air Canada reviews

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

The staff were so kind and helpful. We flew back from NY with another airline and it was horrible. We will always stick with Air Canada as everything was far better!

The boarding process in Toronto bad as they share space with domestic flights and when those domestic flights come in you are locked out behind closed doors until they are done and then its a mad rush to get your boarding gates and board. This is not so much due to Air Canada but with the GTAA, but Air Canada could use different gates especially early morning in order to prevent such travel angst.

Terrible quality wifi and they charge a lot for it. They nickel and dime you for everything.

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.
27/5Mon
directUnited Airlines
2h 02mYYZ-ORD
£121
1/6Sat
1 stopDelta
5h 03mYYZ-ORD
£125
24/5Fri
directAir Canada
1h 54mYYZ-ORD
£131
15/5Wed
1 stopDelta
6h 47mYYZ-ORD
£134
15/5Wed
directAir Canada
1h 59mYYZ-ORD
£135
27/5Mon
1 stopDelta
4h 16mYYZ-ORD
£136
26/6Wed
1 stopWestJet
17h 10mYYZ-ORD
£153
15/5Wed
2 stopsAmerican Airlines
13h 40mYYZ-ORD
£156
10/5Fri
2 stopsWestJet
11h 40mYYZ-ORD
£160
24/5Fri
2 stops
21h 20mYYZ-ORD
£175

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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.
26/4Fri
multi-stopDelta
5h 05mYYZ-ORD
2/5Thu
multi-stopDelta
7h 24mORD-YYZ
£348
27/4Sat
multi-stopDelta
4h 10mYYZ-ORD
1/5Wed
multi-stopDelta
7h 19mORD-YYZ
£348
29/4Mon
multi-stopDelta
7h 50mYYZ-ORD
2/5Thu
multi-stopDelta
7h 24mORD-YYZ
£355
26/4Fri
multi-stopWestJet
4h 10mYYZ-ORD
30/4Tue
multi-stopWestJet
6h 25mORD-YYZ
£371
29/4Mon
multi-stop
6h 09mYYZ-ORD
3/5Fri
direct
1h 45mORD-YYZ
£372
29/4Mon
multi-stopWestJet
8h 20mYYZ-ORD
29/4Mon
multi-stopWestJet
4h 55mORD-YYZ
£378
29/4Mon
directAir Canada
1h 54mYYZ-ORD
29/4Mon
directAir Canada
1h 45mORD-YYZ
£400
29/4Mon
multi-stopAmerican Airlines
5h 54mYYZ-ORD
29/4Mon
directAmerican Airlines
1h 45mORD-YYZ
£407
29/4Mon
direct
1h 54mYYZ-ORD
29/4Mon
multi-stop
34h 00mORD-YYZ
£461
29/4Mon
multi-stopAmerican Airlines
7h 54mYYZ-ORD
29/4Mon
multi-stopAmerican Airlines
14h 30mORD-YYZ
£531

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Toronto - Chicago Flights

Departure:

Toronto (YYZ)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Toronto

Cabin classes:

£886
£1,290
£248

Browse origins:

  • Flights » 
  • Toronto Pearson Airport

Browse destinations:

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