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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 182

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto Pearson Intl Airport to Chicago departing on 19/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Toronto Pearson Intl Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto Pearson Intl Airport to Chicago.

Cheap last-minute flights

Planning a quick getaway from Toronto Pearson Intl Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Toronto Pearson Intl Airport to Chicago

Find recent round-trip train or bus tickets from Toronto Pearson Intl Airport to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:00 a.m. - 2:23 p.m.YYZ-ORD
8h 23m1 stop
3:16 p.m. - 11:53 p.m.ORD-YYZ
7h 37m1 stop
C$ 325
Find Deal
Fri, 24 Jan - Mon, 27 Jan
7:00 a.m. - 1:54 p.m.YYZ-ORD
7h 54m1 stop
3:25 p.m. - 11:53 p.m.ORD-YYZ
7h 28m1 stop
C$ 339
Find Deal
Thu, 9 Jan - Mon, 13 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
9:49 a.m. - 12:30 p.m.ORD-YYZ
1h 41mdirect
C$ 368American Airlines
Find Deal
Thu, 23 Jan - Sun, 26 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
6:00 a.m. - 11:45 a.m.ORD-YYZ
4h 45m1 stop
C$ 381American Airlines
Find Deal
Thu, 23 Jan - Sun, 26 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 414Air Canada
Find Deal
Wed, 8 Jan - Fri, 31 Jan
8:00 a.m. - 8:57 a.m.YYZ-ORD
1h 57mdirect
7:20 a.m. - 1:41 p.m.ORD-YYZ
5h 21m1 stop
C$ 421Air Canada
Find Deal
Fri, 24 Jan - Mon, 27 Jan
6:00 a.m. - 9:16 a.m.YYZ-ORD
4h 16m1 stop
4:15 p.m. - 11:07 p.m.ORD-YYZ
5h 52m1 stop
C$ 430WestJet
Find Deal
Fri, 24 Jan - Mon, 3 Feb
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
11:19 a.m. - 11:11 p.m.MDW-YYZ
10h 52m1 stop
C$ 430WestJet
Find Deal
Thu, 30 Jan - Sat, 1 Feb
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 431United Airlines
Find Deal
Sun, 19 Jan - Wed, 22 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
8:50 a.m. - 2:18 p.m.ORD-YYZ
4h 28m1 stop
C$ 437United Airlines
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Tue, 7 Jan - Wed, 8 Jan
7:00 a.m. - 2:25 p.m.YYZ-ORD
8h 25m1 stop
C$ 182
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Wed, 19 Feb
8:35 a.m. - 6:13 p.m.YYZ-ORD
10h 38m1 stop
C$ 193
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Wed, 19 Feb
1:14 p.m. - 2:14 p.m.YYZ-ORD
2h 00mdirect
C$ 218American Airlines
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Tue, 21 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
C$ 234American Airlines
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Sat, 18 Jan
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
C$ 236United Airlines
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Sun, 19 Jan
6:30 a.m. - 12:42 p.m.YYZ-MDW
7h 12m1 stop
C$ 246WestJet
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Fri, 21 Feb
7:00 a.m. - 9:58 p.m.YYZ-ORD
15h 58m2 stops
C$ 249WestJet
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Sat, 18 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
C$ 250United Airlines
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Sun, 19 Jan
12:30 a.m. - 8:00 a.m.YYZ-ORD
8h 30m1 stop
C$ 282Air Canada
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Tue, 21 Jan
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
C$ 287Air Canada
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Sun, 30 Mar
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
3:00 p.m. - 5:35 p.m.ORD-YYZ
1h 35mdirect
C$ 543American Airlines
Find Deal
Wed, 25 Dec - Sat, 25 Jan
12:30 a.m. - 8:03 a.m.YYZ-ORD
8h 33m1 stop
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 549Air Canada
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Fri, 27 Dec - Fri, 31 Jan
12:30 a.m. - 8:03 a.m.YYZ-ORD
8h 33m1 stop
7:20 a.m. - 1:41 p.m.ORD-YYZ
5h 21m1 stop
C$ 556Air Canada
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Fri, 27 Dec - Fri, 31 Jan
11:40 a.m. - 12:40 p.m.YYZ-ORD
2h 00mdirect
7:00 a.m. - 3:46 p.m.ORD-YYZ
7h 46m1 stop
C$ 558American Airlines
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Wed, 25 Dec - Sat, 25 Jan
5:15 p.m. - 4:40 p.m.YYZ-ORD
24h 25m1 stop
6:45 a.m. - 10:52 p.m.ORD-YYZ
15h 07m1 stop
C$ 596WestJet
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Thu, 26 Dec - Wed, 29 Jan
6:35 p.m. - 7:32 p.m.YYZ-ORD
1h 57mdirect
9:05 p.m. - 8:34 a.m.ORD-YYZ
10h 29m1 stop
C$ 605United Airlines
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Fri, 27 Dec - Mon, 30 Dec
5:15 p.m. - 4:40 p.m.YYZ-ORD
24h 25m1 stop
6:15 a.m. - 6:18 a.m.ORD-YYZ
23h 03m2 stops
C$ 609WestJet
Find Deal
Thu, 26 Dec - Wed, 29 Jan
1:00 p.m. - 4:10 p.m.YYZ-MDW
4h 10m1 stop
9:34 a.m. - 5:31 p.m.MDW-YYZ
6h 57m1 stop
C$ 609Delta
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Wed, 25 Dec - Sat, 25 Jan
7:40 p.m. - 11:25 p.m.YYZ-ORD
4h 45m1 stop
8:30 p.m. - 11:11 p.m.ORD-YYZ
1h 41mdirect
C$ 614United Airlines
Find Deal
Fri, 27 Dec - Sat, 4 Jan
5:15 p.m. - 8:59 p.m.YYZ-ORD
4h 44m1 stop
7:00 a.m. - 11:22 a.m.ORD-YYZ
3h 22m1 stop
C$ 805Delta
Find Deal
Mon, 23 Dec - Fri, 27 Dec
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
9:49 a.m. - 12:30 p.m.ORD-YYZ
1h 41mdirect
C$ 368American Airlines
Find Deal
Thu, 23 Jan - Sun, 26 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 369American Airlines
Find Deal
Sat, 18 Jan - Sun, 2 Feb
11:31 a.m. - 12:31 p.m.YYZ-ORD
2h 00mdirect
3:00 p.m. - 5:35 p.m.ORD-YYZ
1h 35mdirect
C$ 391British Airways
Find Deal
Tue, 4 Feb - Tue, 11 Feb
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 397American Airlines
Find Deal
Tue, 7 Jan - Tue, 28 Jan
11:31 a.m. - 12:31 p.m.YYZ-ORD
2h 00mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 399American Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
6:35 p.m. - 9:20 p.m.ORD-YYZ
1h 45mdirect
C$ 401American Airlines
Find Deal
Wed, 15 Jan - Mon, 20 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 414Air Canada
Find Deal
Wed, 8 Jan - Fri, 31 Jan
9:00 a.m. - 10:10 a.m.YYZ-ORD
2h 10mdirect
4:51 p.m. - 7:45 p.m.ORD-YYZ
1h 54mdirect
C$ 424United Airlines
Find Deal
Tue, 7 Jan - Wed, 8 Jan
8:00 a.m. - 8:57 a.m.YYZ-ORD
1h 57mdirect
8:30 p.m. - 11:11 p.m.ORD-YYZ
1h 41mdirect
C$ 427Air Canada
Find Deal
Fri, 24 Jan - Mon, 27 Jan
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 431United Airlines
Find Deal
Sun, 19 Jan - Wed, 22 Jan

British Airways flights from Toronto Pearson Intl Airport to Chicago

Our best British Airways deals on Toronto Pearson Intl Airport to Chicago flight tickets
British Airways
4 Feb
YYZ11:31 a.m.Toronto Pearson Intl
2h 00m
ORD12:31 p.m.Chicago O'Hare Intl
11 Feb
ORD3:00 p.m.Chicago O'Hare Intl
1h 35m
YYZ5:35 p.m.Toronto Pearson Intl
British Airways
13 Feb
YYZ4:44 p.m.Toronto Pearson Intl
2h 00m
ORD5:44 p.m.Chicago O'Hare Intl
16 Feb
ORD5:10 a.m.Chicago O'Hare Intl
5h 00m
1 stop
YYZ11:10 a.m.Toronto Pearson Intl

Delta flights from Toronto Pearson Intl Airport to Chicago

Our best Delta deals on Toronto Pearson Intl Airport to Chicago flight tickets
Delta
13 Feb
YYZ10:10 a.m.Toronto Pearson Intl
3h 45m
1 stop
ORD12:55 p.m.Chicago O'Hare Intl
15 Feb
ORD4:15 p.m.Chicago O'Hare Intl
5h 52m
1 stop
YYZ11:07 p.m.Toronto Pearson Intl
Delta
13 Feb
YYZ1:20 p.m.Toronto Pearson Intl
8h 33m
1 stop
ORD8:53 p.m.Chicago O'Hare Intl
16 Feb
ORD6:59 a.m.Chicago O'Hare Intl
8h 10m
1 stop
YYZ4:09 p.m.Toronto Pearson Intl
Delta
6 Jan
YYZ2:45 p.m.Toronto Pearson Intl
8h 13m
1 stop
ORD9:58 p.m.Chicago O'Hare Intl
13 Jan
ORD5:10 p.m.Chicago O'Hare Intl
5h 32m
1 stop
YYZ11:42 p.m.Toronto Pearson Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto Pearson Intl Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of February is another great option to travel to Chicago, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 349.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as C$ 387. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 413. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Toronto Pearson Intl Airport to Chicago when you can find flight prices for as low as C$ 382. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 436 per ticket.

What is the cheapest Toronto Pearson Intl to Chicago flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Toronto Pearson Intl Airport is 48 days out, which is when prices tend to be around C$ 425. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as C$ 498.

What cabin class options are available on Toronto Pearson Intl to Chicago flights?

There are 4 cabin classes available to choose from on Toronto Pearson Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto Pearson Intl Airport to Chicago flights?

You could potentially save up to 16% on your flight if you consider stops on a Toronto Pearson Intl Airport to Chicago flight.

How have Toronto Pearson Intl Airport to Chicago flight prices changed over time?

As of December 2024, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 3% more expensive when compared to flights at the same time last year.

When to book flights from Toronto Pearson Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Pearson Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto Pearson Intl Airport to Chicago (YYZ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago

Best price found

C$ 182

Fastest flight time

1h 51m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto Pearson Intl Airport in the past 72 hours is C$ 182. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is C$ 325.
The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 51m
Direct flights go from Toronto Pearson Intl Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Toronto Pearson Intl to Chicago by plane?

    There are 683.0 km between Toronto Pearson Intl and Chicago. 1h 51m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago?

    Prices for flights from Toronto Pearson Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago?

  • How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Pearson Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Toronto Pearson Intl Airport to Chicago?

  • What is the most popular airline from Toronto Pearson Intl Airport to Chicago?


Best airlines flying from Toronto Pearson Intl Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 278Free CancellationRating
7.9
282 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 314Free CancellationRating
7.0
8,413 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 358Free CancellationRating
7.4
9,028 reviews
Search United Airlines flights
American AirlinesPriceFrom C$ 359Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 456Free CancellationRating
7.2
2,812 reviews
Search WestJet flights
  • United Airlines Flights From Toronto Pearson Intl Airport to Chicago

    United Airlines is one of the most popular airlines flying from Toronto Pearson Intl Airport to Chicago, operating 64 flights/week on average for this route. A good United Airlines flight deal for Toronto Pearson Intl Airport to Chicago starts from C$ 249 round-trip, up to an average price of C$ 321. Our users have rated United Airlines at 7.4/10.

  • American Airlines Flights From Toronto Pearson Intl Airport to Chicago

    American Airlines is also a popular choice for this route. American Airlines flight deals for Toronto Pearson Intl Airport to Chicago start from as low as C$ 250 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around C$ 383. American Airlines operates 17 flights to Chicago from Toronto Pearson Intl Airport in an average week. Users have rated it 7.2/10 across 10,000 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Toronto to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Toronto to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Toronto to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago