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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 173

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 5/7. 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 from Toronto Pearson Intl Airport to Chicago

The cheapest plane tickets from Toronto Pearson Intl Airport to Chicago found on KAYAK recently.
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 343American Airlines
Find Deal
Sat, 1 Mar - Wed, 5 Mar
1:15 p.m. - 2:10 p.m.YYZ-ORD
1h 55mdirect
8:10 a.m. - 10:50 a.m.ORD-YYZ
1h 40mdirect
C$ 348American Airlines
Find Deal
Thu, 10 Apr - Sat, 12 Apr
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
8:30 p.m. - 11:11 p.m.ORD-YYZ
1h 41mdirect
C$ 351Air Canada
Find Deal
Sun, 16 Feb - Sun, 23 Feb
9:00 p.m. - 10:06 p.m.YYZ-ORD
2h 06mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 354Air Canada
Find Deal
Thu, 13 Feb - Thu, 20 Feb
6:40 p.m. - 7:37 p.m.YYZ-ORD
1h 57mdirect
9:50 a.m. - 12:25 p.m.ORD-YYZ
1h 35mdirect
C$ 356
Find Deal
Wed, 12 Feb - Sat, 22 Feb
3:50 p.m. - 10:40 a.m.YYZ-ORD
19h 50m2 stops
2:29 p.m. - 12:12 a.m.ORD-YYZ
8h 43m1 stop
C$ 371
Find Deal
Tue, 18 Feb - Tue, 25 Feb
6:30 a.m. - 11:30 a.m.YYZ-ORD
6h 00m1 stop
6:15 a.m. - 1:44 p.m.ORD-YYZ
6h 29m1 stop
C$ 406WestJet
Find Deal
Thu, 13 Feb - Mon, 17 Feb
6:30 a.m. - 5:43 p.m.YYZ-MDW
12h 13m1 stop
1:26 p.m. - 11:07 p.m.MDW-YYZ
8h 41m1 stop
C$ 406WestJet
Find Deal
Fri, 21 Feb - Mon, 24 Feb
9:00 a.m. - 10:04 a.m.YYZ-ORD
2h 04mdirect
1:04 p.m. - 3:45 p.m.ORD-YYZ
1h 41mdirect
C$ 426United Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
6:52 a.m. - 8:01 a.m.YYZ-ORD
2h 09mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 439United Airlines
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Fri, 14 Feb - Sun, 16 Feb
12:00 p.m. - 12:54 p.m.YYZ-ORD
1h 54mdirect
C$ 173Air Canada
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Sat, 5 Jul
12:25 p.m. - 11:58 p.m.YYZ-ORD
12h 33m1 stop
C$ 202
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Wed, 19 Feb
1:14 p.m. - 2:14 p.m.YYZ-ORD
2h 00mdirect
C$ 206American Airlines
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Fri, 21 Feb
5:15 p.m. - 10:40 a.m.YYZ-ORD
18h 25m1 stop
C$ 207
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Mon, 24 Feb
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
C$ 215American Airlines
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Thu, 20 Feb
1:14 p.m. - 2:14 p.m.YYZ-ORD
2h 00mdirect
C$ 222British Airways
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Wed, 12 Feb
1:00 p.m. - 2:05 p.m.YYZ-ORD
2h 05mdirect
C$ 232United Airlines
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Fri, 18 Apr
6:30 a.m. - 12:42 p.m.YYZ-MDW
7h 12m1 stop
C$ 239WestJet
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Thu, 13 Feb
6:30 a.m. - 12:42 p.m.YYZ-MDW
7h 12m1 stop
C$ 245WestJet
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Sun, 23 Feb
1:00 p.m. - 2:05 p.m.YYZ-ORD
2h 05mdirect
C$ 246United Airlines
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Sun, 20 Apr
7:50 p.m. - 12:57 p.m.YYZ-ORD
18h 07m1 stop
6:06 p.m. - 11:45 a.m.ORD-YYZ
16h 39m1 stop
C$ 425
Find Deal
Fri, 24 Jan - Mon, 27 Jan
7:50 p.m. - 12:57 p.m.YYZ-ORD
18h 07m1 stop
6:15 p.m. - 11:25 a.m.ORD-YYZ
16h 10m1 stop
C$ 430
Find Deal
Fri, 24 Jan - Mon, 27 Jan
7:50 p.m. - 9:39 a.m.YYZ-ORD
14h 49m1 stop
5:35 a.m. - 5:15 p.m.ORD-YYZ
10h 40m2 stops
C$ 458
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Sun, 26 Jan - Tue, 28 Jan
11:31 a.m. - 12:31 p.m.YYZ-ORD
2h 00mdirect
6:35 p.m. - 9:20 p.m.ORD-YYZ
1h 45mdirect
C$ 533American Airlines
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Sun, 26 Jan - Wed, 29 Jan
6:45 p.m. - 7:42 p.m.YYZ-ORD
1h 57mdirect
1:55 p.m. - 9:35 p.m.ORD-YYZ
6h 40m1 stop
C$ 547Air Canada
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Sun, 26 Jan - Wed, 29 Jan
12:20 p.m. - 6:38 p.m.YYZ-ORD
7h 18m1 stop
7:20 a.m. - 1:41 p.m.ORD-YYZ
5h 21m1 stop
C$ 554Air Canada
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Sun, 26 Jan - Wed, 29 Jan
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$ 605American Airlines
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Thu, 23 Jan - Sun, 2 Feb
10:05 a.m. - 4:13 p.m.YYZ-ORD
7h 08m1 stop
6:45 a.m. - 11:59 a.m.ORD-YYZ
4h 14m1 stop
C$ 622WestJet
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Thu, 23 Jan - Sun, 2 Feb
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
1:26 p.m. - 11:11 p.m.MDW-YYZ
8h 45m1 stop
C$ 633WestJet
Find Deal
Thu, 23 Jan - Wed, 29 Jan
5:15 p.m. - 10:59 p.m.YYZ-ORD
6h 44m1 stop
7:05 a.m. - 9:58 a.m.ORD-YYZ
1h 53mdirect
C$ 733United Airlines
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Wed, 22 Jan - Thu, 23 Jan
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 343American Airlines
Find Deal
Sat, 1 Mar - Wed, 5 Mar
1:15 p.m. - 2:10 p.m.YYZ-ORD
1h 55mdirect
8:10 a.m. - 10:50 a.m.ORD-YYZ
1h 40mdirect
C$ 348American Airlines
Find Deal
Thu, 10 Apr - Sat, 12 Apr
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
8:30 p.m. - 11:11 p.m.ORD-YYZ
1h 41mdirect
C$ 351Air Canada
Find Deal
Sun, 16 Feb - Sun, 23 Feb
9:00 p.m. - 10:06 p.m.YYZ-ORD
2h 06mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 354Air Canada
Find Deal
Thu, 13 Feb - Thu, 20 Feb
6:40 p.m. - 7:37 p.m.YYZ-ORD
1h 57mdirect
9:50 a.m. - 12:25 p.m.ORD-YYZ
1h 35mdirect
C$ 356
Find Deal
Wed, 12 Feb - Sat, 22 Feb
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
9:12 p.m. - 11:59 p.m.ORD-YYZ
1h 47mdirect
C$ 366Air Canada
Find Deal
Fri, 7 Feb - Sun, 23 Feb
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
9:12 p.m. - 11:59 p.m.ORD-YYZ
1h 47mdirect
C$ 405
Find Deal
Thu, 13 Feb - Sun, 16 Feb
9:00 a.m. - 10:04 a.m.YYZ-ORD
2h 04mdirect
11:04 a.m. - 1:42 p.m.ORD-YYZ
1h 38mdirect
C$ 415Lufthansa
Find Deal
Thu, 13 Feb - Sun, 16 Feb
9:00 a.m. - 10:04 a.m.YYZ-ORD
2h 04mdirect
1:04 p.m. - 3:45 p.m.ORD-YYZ
1h 41mdirect
C$ 426United Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:00 a.m. - 12:09 p.m.YYZ-ORD
2h 09mdirect
9:12 p.m. - 11:59 p.m.ORD-YYZ
1h 47mdirect
C$ 432United Airlines
Find Deal
Thu, 13 Mar - Fri, 14 Mar

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
YYZ6:00 a.m.Toronto Pearson Intl
4h 16m
1 stop
ORD9:16 a.m.Chicago O'Hare Intl
15 Feb
ORD4:58 p.m.Chicago O'Hare Intl
4h 51m
1 stop
YYZ10:49 p.m.Toronto Pearson Intl
Delta
13 Feb
YYZ6:00 a.m.Toronto Pearson Intl
4h 16m
1 stop
ORD9:16 a.m.Chicago O'Hare Intl
16 Feb
ORD6:59 a.m.Chicago O'Hare Intl
3h 57m
1 stop
YYZ11:56 a.m.Toronto Pearson Intl
Delta
7 Feb
YYZ6:00 a.m.Toronto Pearson Intl
4h 16m
1 stop
ORD9:16 a.m.Chicago O'Hare Intl
10 Feb
ORD2:35 p.m.Chicago O'Hare Intl
4h 53m
1 stop
YYZ8:28 p.m.Toronto Pearson Intl

WestJet flights from Toronto Pearson Intl Airport to Chicago

Our best WestJet deals on Toronto Pearson Intl Airport to Chicago flight tickets
WestJet
13 Feb
YYZ6:30 a.m.Toronto Pearson Intl
6h 00m
1 stop
ORD11:30 a.m.Chicago O'Hare Intl
17 Feb
ORD6:15 a.m.Chicago O'Hare Intl
6h 29m
1 stop
YYZ1:44 p.m.Toronto Pearson Intl
WestJet
17 Mar
YYZ6:15 p.m.Toronto Pearson Intl
15h 54m
1 stop
MDW9:09 a.m.Chicago Midway
19 Mar
MDW1:16 p.m.Chicago Midway
23h 17m
1 stop
YYZ1:33 p.m.Toronto Pearson Intl
WestJet
1 Apr
YYZ2:45 p.m.Toronto Pearson Intl
4h 33m
1 stop
MDW6:18 p.m.Chicago Midway
4 Apr
MDW1:15 p.m.Chicago Midway
23h 20m
1 stop
YYZ1:35 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 July is another great option to travel to Chicago, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 386.

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$ 388. 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$ 414. 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?

You are more likely to see cheaper flights to Chicago from Toronto Pearson Intl Airport when booking 18 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 437 when searching 18 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto Pearson Intl Airport for as low as C$ 383 on momondo.

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.

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

As of January 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 27% 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$ 173

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$ 173. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is C$ 343.
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$ 279Free CancellationRating
7.9
277 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 321Free CancellationRating
7.0
8,635 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 359Free CancellationRating
7.4
8,985 reviews
Search United Airlines flights
American AirlinesPriceFrom C$ 359Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 457Free CancellationRating
7.2
2,829 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 65 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$ 325. 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$ 382. American Airlines operates 22 flights to Chicago from Toronto Pearson Intl Airport in an average week. Users have rated it 7.2/10 across 10,000 reviews.


Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Merrillville

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago