YYZ - ORD

£106 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 17/1. 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
In the last 7 days, travellers have searched 41,299,237 times on KAYAK, and here's why:

Save 30% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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 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.

Recent return flight deals from Toronto to Chicago

Recommended round-trip 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
20:25 - 23:06ORD-YYZ
1h 41mdirect
£174United Airlines
Find Deal
Fri, 10 Jan - Fri, 10 Jan
14:05 - 18:38YYZ-ORD
5h 33m1 stop
20:30 - 23:11ORD-YYZ
1h 41mdirect
£188Air Canada
Find Deal
Sat, 18 Jan - Sun, 19 Jan
12:20 - 13:11YYZ-ORD
1h 51mdirect
09:50 - 12:30ORD-YYZ
1h 40mdirect
£189Air Canada
Find Deal
Sat, 18 Jan - Sun, 19 Jan
07:20 - 19:23YYZ-ORD
13h 03m1 stop
11:35 - 18:05ORD-YYZ
5h 30m1 stop
Sun, 26 Jan - Mon, 27 Jan
14:45 - 21:58YYZ-ORD
8h 13m1 stop
10:30 - 19:06ORD-YYZ
7h 36m1 stop
£194Delta
Find Deal
Mon, 6 Jan - Thu, 6 Feb
07:55 - 16:09YYZ-ORD
9h 14m1 stop
07:30 - 16:08ORD-YYZ
7h 38m1 stop
£197Delta
Find Deal
Wed, 12 Feb - Wed, 26 Feb
14:45 - 23:25YYZ-ORD
9h 40m1 stop
15:35 - 23:50ORD-YYZ
7h 15m1 stop
Fri, 3 Jan - Wed, 8 Jan
06:15 - 13:03YYZ-ORD
7h 48m1 stop
09:30 - 23:33ORD-YYZ
13h 03m2 stops
£239WestJet
Find Deal
Sat, 29 Mar - Tue, 1 Apr
06:00 - 09:16YYZ-ORD
4h 16m1 stop
06:15 - 23:34ORD-YYZ
16h 19m2 stops
£240WestJet
Find Deal
Thu, 9 Jan - Mon, 13 Jan
00:40 - 18:00YYZ-ORD
18h 20m1 stop
16:05 - 11:25ORD-YYZ
18h 20m1 stop
£8,875Austrian Airlines
Find Deal
Wed, 19 Mar - Sun, 30 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 January, where tickets cost £197 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is £258 and £252 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.
Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at £254 on average.

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

£106
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly (6% 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 £134 for a one-way ticket and £220 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 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 £166 or less one-way and £180 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 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, +10 more

ANA, Air Canada, +11 more

Tuesday

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

ANA, Air Canada, +11 more

Wednesday

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

ANA, Air Canada, +11 more

Thursday

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

ANA, Air Canada, +11 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 8382 reviews
7.0Comfort
7.8Crew
6.3Food
7.3Boarding
6.8Entertainment
Airline reviews

The idea of needing to go outside in the winter to board in icy cold temperatures is totally a non starter for me. Seats were very uncomfortable though the leg room not too terrible. Attendants were nice

4.0 OkayLucinda, Dec 2024YYZ - PHL
Read more Air Canada reviews

The idea of needing to go outside in the winter to board in icy cold temperatures is totally a non starter for me. Seats were very uncomfortable though the leg room not too terrible. Attendants were nice

The experience was good. Flight was on time. Liked how they offered to accept carryon baggage for free before as I was checking in online.

Flight was delayed by 45 min. No problems. Everyone took it in stride.

Crew was friendly and helpful; cabin seemed roomy even in economy class.

The flight attendants that assisted me were exceptionally nice, kind and helpful

Something wrong with the plane so had to deplane and waited over 2 hours to finally leave

AC needs to update their fleet. Too many mechanical issues, dated planes and too many delays

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

was wondreful! just let me know what airline im flying in advance!

On this flight, we didn't even get water offered, nor any other beverage. Therefore we got a snack of pretzels. Flight was good and Air Canada a good airline

Book cheap flights from Toronto to Chicago

Cheapest flights to Chicago from Toronto found in 2024 and 2025

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.
17/1Fri
directUnited Airlines
1h 57mYYZ-ORD
£106
15/1Wed
1 stopUnited Airlines
7h 18mYYZ-ORD
£110
15/1Wed
1 stopDelta
9h 18mYYZ-ORD
£118
15/2Sat
1 stopDelta
7h 12mYYZ-ORD
£120
29/3Sat
1 stopWestJet
23h 53mYYZ-ORD
£140
24/3Mon
1 stopWestJet
21h 43mYYZ-ORD
£140
24/3Mon
directAir Canada
1h 51mYYZ-ORD
£143
24/3Mon
1 stopAir Canada
5h 45mYYZ-ORD
£145
18/3Tue
1 stopAustrian Airlines
18h 20mYYZ-ORD
£2,829
18/3Tue
1 stopAustrian Airlines
18h 20mYYZ-ORD
£2,839

Search by stops

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Search by price

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.
21/12Sat
multi-stopUnited Airlines
9h 40mYYZ-ORD
31/12Tue
directUnited Airlines
1h 41mORD-YYZ
£339
20/12Fri
directUnited Airlines
1h 58mYYZ-ORD
5/1Sun
multi-stopUnited Airlines
14h 01mORD-YYZ
£353
22/12Sun
multi-stopDelta
7h 35mYYZ-ORD
28/12Sat
multi-stopDelta
8h 14mORD-YYZ
£391
21/12Sat
direct
1h 51mYYZ-ORD
23/12Mon
multi-stop
5h 21mORD-YYZ
£402
21/12Sat
multi-stop
9h 40mYYZ-ORD
23/12Mon
multi-stop
5h 30mORD-YYZ
£406
19/12Thu
multi-stopDelta
4h 03mYYZ-ORD
26/12Thu
multi-stopDelta
8h 14mORD-YYZ
£414
19/12Thu
multi-stopWestJet
7h 35mYYZ-ORD
30/12Mon
multi-stopWestJet
9h 59mORD-YYZ
£424
23/12Mon
multi-stopWestJet
10h 37mYYZ-ORD
27/12Fri
multi-stopWestJet
21h 39mORD-YYZ
£427
19/12Thu
multi-stopAlaska Airlines
23h 30mYYZ-ORD
3/1Fri
multi-stopAlaska Airlines
19h 00mORD-YYZ
£1,342
19/12Thu
multi-stopAlaska Airlines
23h 30mYYZ-ORD
3/1Fri
multi-stopAlaska Airlines
19h 00mORD-YYZ
£1,401

Search by stops

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

Information on your arrival and departure airports

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