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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 136

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 1/11. 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

Air Canada Logo
8:15 a.m. - 9:13 a.m.YYZ-ORD
1h 58mdirect
Air Canada Logo
2:00 p.m. - 4:39 p.m.ORD-YYZ
1h 39mdirect
C$ 203Air Canada
Find Deal
Fri, 7 Nov - Sun, 16 Nov
Air Canada Logo
8:15 a.m. - 9:15 a.m.YYZ-ORD
2h 00mdirect
Air Canada Logo
10:00 a.m. - 12:40 p.m.ORD-YYZ
1h 40mdirect
C$ 219Air Canada
Find Deal
Fri, 31 Oct - Mon, 3 Nov
American Airlines Logo
4:44 p.m. - 5:44 p.m.YYZ-ORD
2h 00mdirect
American Airlines Logo
5:00 a.m. - 11:03 a.m.ORD-YYZ
5h 03m1 stop
C$ 233American Airlines
Find Deal
Fri, 7 Nov - Sun, 16 Nov
United Airlines Logo
8:55 a.m. - 10:00 a.m.YYZ-ORD
2h 05mdirect
United Airlines Logo
7:10 a.m. - 9:58 a.m.ORD-YYZ
1h 48mdirect
C$ 245United Airlines
Find Deal
Fri, 7 Nov - Sun, 9 Nov
American Airlines Logo
11:44 a.m. - 12:39 p.m.YYZ-ORD
1h 55mdirect
American Airlines Logo
11:49 a.m. - 5:19 p.m.ORD-YYZ
4h 30m1 stop
C$ 248American Airlines
Find Deal
Tue, 16 Sep - Tue, 23 Sep
United Airlines Logo
7:40 p.m. - 11:43 p.m.YYZ-ORD
5h 03m1 stop
United Airlines Logo
11:15 a.m. - 2:01 p.m.ORD-YYZ
1h 46mdirect
C$ 252United Airlines
Find Deal
Fri, 7 Nov - Sun, 9 Nov
Delta Logo
2:30 p.m. - 10:26 p.m.YYZ-ORD
8h 56m1 stop
Delta Logo
4:56 p.m. - 10:55 p.m.ORD-YYZ
4h 59m1 stop
C$ 278Delta
Find Deal
Tue, 14 Oct - Sat, 18 Oct
Delta Logo
12:15 p.m. - 6:04 p.m.YYZ-ORD
6h 49m1 stop
Delta Logo
7:10 a.m. - 3:22 p.m.ORD-YYZ
7h 12m1 stop
C$ 292Delta
Find Deal
Thu, 11 Sep - Thu, 2 Oct
WestJet Logo
1:20 p.m. - 9:26 p.m.YYZ-MDW
9h 06m1 stop
WestJet Logo
10:31 a.m. - 4:57 p.m.MDW-YYZ
5h 26m1 stop
C$ 360WestJet
Find Deal
Wed, 3 Sep - Sat, 6 Sep
WestJet Logo
11:52 a.m. - 10:14 p.m.YYZ-MDW
11h 22m1 stop
WestJet Logo
9:20 a.m. - 6:30 p.m.MDW-YYZ
8h 10m1 stop
C$ 365WestJet
Find Deal
Fri, 17 Oct - Tue, 21 Oct

United Airlines flights from Toronto Pearson Intl Airport to Chicago

Our best United Airlines deals on Toronto Pearson Intl Airport to Chicago flight tickets
United Airlines
7 Nov
YYZ8:55 a.m.Toronto Pearson Intl
2h 05m
ORD10:00 a.m.Chicago O'Hare Intl
9 Nov
ORD7:10 a.m.Chicago O'Hare Intl
1h 48m
YYZ9:58 a.m.Toronto Pearson Intl
C$ 245
Find similar
United Airlines
7 Nov
YYZ7:40 p.m.Toronto Pearson Intl
5h 03m
1 stop
ORD11:43 p.m.Chicago O'Hare Intl
9 Nov
ORD11:15 a.m.Chicago O'Hare Intl
1h 46m
YYZ2:01 p.m.Toronto Pearson Intl
C$ 252
Find similar
United Airlines
7 Nov
YYZ7:40 p.m.Toronto Pearson Intl
5h 03m
1 stop
ORD11:43 p.m.Chicago O'Hare Intl
9 Nov
ORD6:28 p.m.Chicago O'Hare Intl
1h 53m
YYZ9:21 p.m.Toronto Pearson Intl
C$ 254
Find similar

Air Canada flights from Toronto Pearson Intl Airport to Chicago

Our best Air Canada deals on Toronto Pearson Intl Airport to Chicago flight tickets
Air Canada
7 Nov
YYZ8:15 a.m.Toronto Pearson Intl
1h 58m
ORD9:13 a.m.Chicago O'Hare Intl
16 Nov
ORD2:00 p.m.Chicago O'Hare Intl
1h 39m
YYZ4:39 p.m.Toronto Pearson Intl
C$ 203
Find similar
Air Canada
31 Oct
YYZ8:15 a.m.Toronto Pearson Intl
2h 00m
ORD9:15 a.m.Chicago O'Hare Intl
3 Nov
ORD10:00 a.m.Chicago O'Hare Intl
1h 40m
YYZ12:40 p.m.Toronto Pearson Intl
C$ 219
Find similar
Air Canada
6 Oct
YYZ4:40 p.m.Toronto Pearson Intl
1h 53m
ORD5:33 p.m.Chicago O'Hare Intl
8 Oct
ORD8:25 p.m.Chicago O'Hare Intl
1h 43m
YYZ11:08 p.m.Toronto Pearson Intl
C$ 225
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Pearson Intl Airport to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 4 August 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/11

8:15 a.m.-9:13 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sun 16/11

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

C$ 203

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 31/10

8:15 a.m.-9:15 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 3/11

10:00 a.m.-12:40 p.m.

Nonstop1h 40m

C$ 219

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/11

4:44 p.m.-5:44 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 16/11

5:00 a.m.-11:03 a.m.

1 stop5h 03m

C$ 233

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/11

8:55 a.m.-10:00 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 9/11

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 16/9

11:44 a.m.-12:39 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Tue 23/9

11:49 a.m.-5:19 p.m.

1 stop4h 30m

C$ 248

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/11

7:40 p.m.-11:43 p.m.

1 stop5h 03m

Chicago O'Hare Intl

Sun 9/11

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

C$ 252

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 14/10

2:30 p.m.-10:26 p.m.

1 stop8h 56m

Chicago O'Hare Intl

Sat 18/10

4:56 p.m.-10:55 p.m.

1 stop4h 59m

C$ 278

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/9

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago O'Hare Intl

Thu 2/10

7:10 a.m.-3:22 p.m.

1 stop7h 12m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 3/9

1:20 p.m.-9:26 p.m.

1 stop9h 06m

Chicago Midway

Sat 6/9

10:31 a.m.-4:57 p.m.

1 stop5h 26m

C$ 360

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 17/10

11:52 a.m.-10:14 p.m.

1 stop11h 22m

Chicago Midway

Tue 21/10

9:20 a.m.-6:30 p.m.

1 stop8h 10m

C$ 365

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 June is another great option to travel to Chicago, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 354.

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 Friday when prices can be found for as low as C$ 684. 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 Tuesday because tickets tend to average around C$ 1,225. 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 evening 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$ 592. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,421 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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 407 when searching 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$ 331 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 August 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 22% cheaper 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$ 136

Fastest flight time

1h 53m

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$ 136. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is C$ 203.
The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 53m
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)
Search flight deals

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

    There are 683.0 km between Toronto Pearson Intl and Chicago. 1h 53m 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$ 227Free CancellationRating
8.0
321 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 266Free CancellationRating
7.1
9,879 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 281Free CancellationRating
7.4
8,912 reviews
Search United Airlines flights
American AirlinesPriceFrom C$ 289Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 422Free CancellationRating
7.2
2,994 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 83 flights/week on average for this route. A good United Airlines flight deal for Toronto Pearson Intl Airport to Chicago starts from C$ 203 round-trip, up to an average price of C$ 310. 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$ 210 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around C$ 358. American Airlines operates 23 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
Hammond
Munster
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
Chicago Midway Airport
Chicago O'Hare Intl Airport