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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 164

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 25/2. 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

Enter your travel dates to find the best prices.
Air Canada Logo
2:15 p.m. - 3:10 p.m.
YYZ
-
ORD
1h 55mdirect
Air Canada Logo
8:00 a.m. - 10:40 a.m.
ORD
-
YYZ
1h 40mdirect
C$ 256Air Canada
Thu, 19 Feb - Mon, 23 Feb
United Airlines Logo
8:45 a.m. - 9:50 a.m.
YYZ
-
ORD
2h 05mdirect
United Airlines Logo
1:12 p.m. - 4:02 p.m.
ORD
-
YYZ
1h 50mdirect
C$ 259United Airlines
Tue, 17 Feb - Tue, 24 Feb
United Airlines Logo
3:30 p.m. - 4:39 p.m.
YYZ
-
ORD
2h 09mdirect
United Airlines Logo
6:28 p.m. - 9:21 p.m.
ORD
-
YYZ
1h 53mdirect
C$ 260United Airlines
Thu, 19 Feb - Mon, 23 Feb
Air Canada Logo
8:00 a.m. - 2:55 p.m.
YYZ
-
ORD
7h 55m
1 stop
Air Canada Logo
10:00 a.m. - 12:40 p.m.
ORD
-
YYZ
1h 40mdirect
C$ 264Air Canada
Thu, 19 Feb - Mon, 23 Feb
Air Canada Logo
4:00 p.m. - 8:10 p.m.
YYZ
-
ORD
5h 10m
1 stop
Air Canada Logo
10:00 a.m. - 12:40 p.m.
ORD
-
YYZ
1h 40mdirect
C$ 268Air Canada
Sat, 21 Feb - Tue, 24 Feb
Lufthansa Logo
3:30 p.m. - 4:39 p.m.
YYZ
-
ORD
2h 09mdirect
Lufthansa Logo
6:28 p.m. - 9:21 p.m.
ORD
-
YYZ
1h 53mdirect
C$ 271Lufthansa
Thu, 19 Feb - Mon, 23 Feb
United Airlines Logo
9:00 p.m. - 10:04 p.m.
YYZ
-
ORD
2h 04mdirect
United Airlines Logo
2:30 p.m. - 9:24 p.m.
ORD
-
YYZ
5h 54m
1 stop
C$ 272United Airlines
Tue, 17 Feb - Tue, 24 Feb
American Airlines Logo
6:00 a.m. - 7:15 a.m.
YYZ
-
ORD
2h 15mdirect
American Airlines Logo
6:08 a.m. - 11:51 a.m.
ORD
-
YYZ
4h 43m
1 stop
C$ 274American Airlines
Thu, 19 Feb - Mon, 23 Feb
American Airlines Logo
1:55 p.m. - 6:24 p.m.
YYZ
-
ORD
5h 29m
1 stop
American Airlines Logo
1:22 p.m. - 4:03 p.m.
ORD
-
YYZ
1h 41mdirect
C$ 281American Airlines
Fri, 6 Mar - Sun, 8 Mar
WestJet Logo
12:11 p.m. - 5:37 p.m.
YYZ
-
MDW
6h 26m
1 stop
WestJet Logo
1:49 p.m. - 11:11 p.m.
MDW
-
YYZ
8h 22m
1 stop
C$ 325WestJet
Mon, 2 Mar - Fri, 6 Mar

Lufthansa flights from Toronto Pearson Intl Airport to Chicago

Our best Lufthansa deals on Toronto Pearson Intl Airport to Chicago flight tickets
Lufthansa
19 Feb
YYZ3:30 p.m.Toronto Pearson Intl
2h 09m
ORD4:39 p.m.Chicago O'Hare Intl
23 Feb
ORD6:28 p.m.Chicago O'Hare Intl
1h 53m
YYZ9:21 p.m.Toronto Pearson Intl
C$ 271
Lufthansa
19 Feb
YYZ8:45 a.m.Toronto Pearson Intl
2h 05m
ORD9:50 a.m.Chicago O'Hare Intl
23 Feb
ORD6:28 p.m.Chicago O'Hare Intl
1h 53m
YYZ9:21 p.m.Toronto Pearson Intl
C$ 292
Lufthansa
31 Jan
YYZ9:00 a.m.Toronto Pearson Intl
2h 06m
ORD10:06 a.m.Chicago O'Hare Intl
31 Jan
ORD6:28 p.m.Chicago O'Hare Intl
1h 53m
YYZ9:21 p.m.Toronto Pearson Intl
C$ 398

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
19 Feb
YYZ2:15 p.m.Toronto Pearson Intl
1h 55m
ORD3:10 p.m.Chicago O'Hare Intl
23 Feb
ORD8:00 a.m.Chicago O'Hare Intl
1h 40m
YYZ10:40 a.m.Toronto Pearson Intl
C$ 256
Air Canada
19 Feb
YYZ8:00 a.m.Toronto Pearson Intl
7h 55m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
23 Feb
ORD10:00 a.m.Chicago O'Hare Intl
1h 40m
YYZ12:40 p.m.Toronto Pearson Intl
C$ 264
Air Canada
21 Feb
YYZ4:00 p.m.Toronto Pearson Intl
5h 10m
1 stop
ORD8:10 p.m.Chicago O'Hare Intl
24 Feb
ORD10:00 a.m.Chicago O'Hare Intl
1h 40m
YYZ12:40 p.m.Toronto Pearson Intl
C$ 268

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 27 January 2026.
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

Thu 19/2

2:15 p.m.-3:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 23/2

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 17/2

8:45 a.m.-9:50 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 24/2

1:12 p.m.-4:02 p.m.

Nonstop1h 50m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 19/2

3:30 p.m.-4:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Mon 23/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 260

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 19/2

8:00 a.m.-2:55 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Mon 23/2

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

Nonstop1h 40m

C$ 264

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 21/2

4:00 p.m.-8:10 p.m.

1 stop5h 10m

Chicago O'Hare Intl

Tue 24/2

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

Nonstop1h 40m

C$ 268

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 19/2

3:30 p.m.-4:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Mon 23/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 271

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 17/2

9:00 p.m.-10:04 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Tue 24/2

2:30 p.m.-9:24 p.m.

1 stop5h 54m

C$ 272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 19/2

6:00 a.m.-7:15 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Mon 23/2

6:08 a.m.-11:51 a.m.

1 stop4h 43m

C$ 274

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/3

1:55 p.m.-6:24 p.m.

1 stop5h 29m

Chicago O'Hare Intl

Sun 8/3

1:22 p.m.-4:03 p.m.

Nonstop1h 41m

C$ 281

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 2/3

12:11 p.m.-5:37 p.m.

1 stop6h 26m

Chicago Midway

Fri 6/3

1:49 p.m.-11:11 p.m.

1 stop8h 22m

C$ 325

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 August is another great option to travel to Chicago, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 330.

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$ 578. 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$ 996. 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$ 640. Flying to Chicago in the evening 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$ 1,099 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$ 392 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$ 267 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.

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

You could potentially save up to 10% 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 January 2026, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 42% 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$ 335

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Toronto Pearson Intl Airport in the past 72 hours is C$ 335. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is C$ 555.
The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 55m
Direct flights go from Toronto Pearson Intl Airport to Chicago every day.
There are 3 airports in Chicago. From Toronto Pearson Intl Airport there are direct flights to Chicago O'Hare Intl (ORD).
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 55m 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$ 112Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
American AirlinesPriceFrom C$ 222Free CancellationRating
7.2
11,197 reviews
Search American Airlines flights
Air CanadaPriceFrom C$ 246Free CancellationRating
7.1
10,660 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 258Free CancellationRating
7.4
9,205 reviews
Search United Airlines flights
WestJetPriceFrom C$ 365Free CancellationRating
7.2
3,251 reviews
Search WestJet flights

  • Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago

    Porter Airlines is one of the most popular airlines flying from Toronto Pearson Intl Airport to Chicago, operating 31 flights/week on average for this route. A good Porter Airlines flight deal for Toronto Pearson Intl Airport to Chicago starts from C$ 112 round-trip, up to an average price of C$ 308. Our users have rated Porter Airlines at 7.9/10.

  • United Airlines Flights From Toronto Pearson Intl Airport to Chicago

    United Airlines is also a popular choice for this route. United Airlines flight deals for Toronto Pearson Intl Airport to Chicago start from as low as C$ 258 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around C$ 394. United Airlines operates 67 flights to Chicago from Toronto Pearson Intl Airport in an average week. Users have rated it 7.4/10 across 9,205 reviews.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
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