YYZ - ORD

£114 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 11/2. 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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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
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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 return 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 return flight deals from Toronto to Chicago

Recommended return deals departing in the coming months from the most popular airlines that fly from Toronto to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
09:00 - 10:10YYZ-ORD
2h 10mdirect
17:01 - 19:45ORD-YYZ
1h 44mdirect
Tue, 11 Feb - Fri, 14 Feb
06:15 - 13:44YYZ-ORD
8h 29m1 stop
06:15 - 13:44ORD-YYZ
6h 29m1 stop
£198Delta
Find Deal
Thu, 13 Feb - Mon, 17 Feb
12:20 - 13:11YYZ-ORD
1h 51mdirect
10:45 - 13:42ORD-YYZ
1h 57mdirect
£213Air Canada
Find Deal
Sun, 20 Apr - Wed, 23 Apr
09:00 - 14:45YYZ-ORD
6h 45m1 stop
20:30 - 23:11ORD-YYZ
1h 41mdirect
£214Air Canada
Find Deal
Mon, 17 Mar - Tue, 18 Mar
13:00 - 14:05YYZ-ORD
2h 05mdirect
16:00 - 18:41ORD-YYZ
1h 41mdirect
£219United Airlines
Find Deal
Mon, 21 Apr - Tue, 22 Apr
12:20 - 13:11YYZ-ORD
1h 51mdirect
16:00 - 18:41ORD-YYZ
1h 41mdirect
£220United Airlines
Find Deal
Tue, 18 Feb - Fri, 21 Feb
16:30 - 21:40YYZ-ORD
6h 10m1 stop
06:05 - 11:51ORD-YYZ
4h 46m1 stop
£226American Airlines
Find Deal
Mon, 17 Mar - Tue, 18 Mar
17:55 - 22:48YYZ-ORD
5h 53m1 stop
16:59 - 23:05ORD-YYZ
5h 06m1 stop
£246American Airlines
Find Deal
Mon, 21 Apr - Wed, 23 Apr
17:05 - 22:36YYZ-ORD
6h 31m1 stop
09:34 - 23:30ORD-YYZ
12h 56m2 stops
£259WestJet
Find Deal
Fri, 21 Feb - Sun, 9 Mar
13:20 - 16:13YYZ-ORD
3h 53m1 stop
10:10 - 23:30ORD-YYZ
12h 20m2 stops
£261WestJet
Find Deal
Sun, 2 Mar - Tue, 4 Mar

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’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, Wednesday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays 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 £228 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is £291 and £271 respectively.

Can I save money by flying with a stopover from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

The average return price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of £398, 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 - Cheap tickets from Toronto to Chicago

Low season

January

High season

August

Cheapest flight

£114
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 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 
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 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 £140 for a one-way ticket and £227 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, 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

  • 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 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 direct 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 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 8633 reviews
6.2Food
7.0Comfort
7.8Crew
7.3Boarding
6.8Entertainment
Airline reviews

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.

2.0 MediocreAnonymous, Jan 2025YYZ - DCA
Read more Air Canada reviews

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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lincolnshire
Joliet
Waukegan
Vernon Hills
Itasca
South Haven
Rockford
Libertyville
Lisle
Deerfield
Oakbrook Terrace
Benton Harbor
Oak Park
Janesville
Great Lakes
Crown Point
Freeport
North Chicago
Warrenville
Glenview

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

Information on your arrival and departure airports

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