Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 167

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 25/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:15 p.m. - 10:56 p.m.YYZ-ORD
5h 41m1 stop
American Airlines Logo
6:06 a.m. - 11:54 a.m.ORD-YYZ
4h 48m1 stop
C$ 258American Airlines
Find Deal
Fri, 21 Nov - Tue, 25 Nov
United Airlines Logo
5:30 p.m. - 6:50 p.m.YYZ-ORD
2h 20mdirect
United Airlines Logo
4:50 p.m. - 7:45 p.m.ORD-YYZ
1h 55mdirect
C$ 259United Airlines
Find Deal
Wed, 28 Jan - Mon, 2 Feb
American Airlines Logo
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
American Airlines Logo
1:16 p.m. - 4:03 p.m.ORD-YYZ
1h 47mdirect
C$ 262American Airlines
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Delta Logo
2:30 p.m. - 7:25 p.m.YYZ-ORD
5h 55m1 stop
Delta Logo
6:45 a.m. - 2:48 p.m.ORD-YYZ
7h 03m1 stop
C$ 281Delta
Find Deal
Wed, 5 Nov - Sun, 9 Nov
Delta Logo
6:15 a.m. - 12:28 p.m.YYZ-MDW
7h 13m1 stop
Delta Logo
3:00 p.m. - 11:18 p.m.MDW-YYZ
7h 18m1 stop
C$ 281Delta
Find Deal
Wed, 5 Nov - Sat, 8 Nov
Air Canada Logo
12:05 p.m. - 1:01 p.m.YYZ-ORD
1h 56mdirect
Air Canada Logo
8:00 a.m. - 10:40 a.m.ORD-YYZ
1h 40mdirect
C$ 322Air Canada
Find Deal
Thu, 4 Dec - Sun, 7 Dec
United Airlines Logo
8:55 a.m. - 10:01 a.m.YYZ-ORD
2h 06mdirect
United Airlines Logo
1:00 p.m. - 6:57 p.m.ORD-YYZ
4h 57m1 stop
C$ 325United Airlines
Find Deal
Fri, 6 Feb - Sun, 8 Feb
Air Canada Logo
10:00 a.m. - 2:55 p.m.YYZ-ORD
5h 55m1 stop
Air Canada Logo
3:55 p.m. - 6:34 p.m.ORD-YYZ
1h 39mdirect
C$ 344Air Canada
Find Deal
Thu, 4 Dec - Sun, 7 Dec
WestJet Logo
9:52 a.m. - 4:24 p.m.YYZ-ORD
7h 32m1 stop
WestJet Logo
7:20 a.m. - 9:53 p.m.ORD-YYZ
13h 33m2 stops
C$ 356WestJet
Find Deal
Thu, 20 Nov - Mon, 24 Nov
WestJet Logo
6:20 a.m. - 10:30 a.m.YYZ-MDW
5h 10m1 stop
WestJet Logo
9:41 a.m. - 4:02 p.m.MDW-YYZ
5h 21m1 stop
C$ 371WestJet
Find Deal
Sat, 8 Nov - Tue, 11 Nov

American Airlines flights from Toronto Pearson Intl Airport to Chicago

Our best American Airlines deals on Toronto Pearson Intl Airport to Chicago flight tickets
American Airlines
21 Nov
YYZ6:15 p.m.Toronto Pearson Intl
5h 41m
1 stop
ORD10:56 p.m.Chicago O'Hare Intl
25 Nov
ORD6:06 a.m.Chicago O'Hare Intl
4h 48m
1 stop
YYZ11:54 a.m.Toronto Pearson Intl
C$ 258
Find similar
American Airlines
26 Nov
YYZ6:20 p.m.Toronto Pearson Intl
2h 00m
ORD7:20 p.m.Chicago O'Hare Intl
3 Dec
ORD1:16 p.m.Chicago O'Hare Intl
1h 47m
YYZ4:03 p.m.Toronto Pearson Intl
C$ 262
Find similar
American Airlines
27 Nov
YYZ11:32 a.m.Toronto Pearson Intl
1h 55m
ORD12:27 p.m.Chicago O'Hare Intl
6 Dec
ORD9:41 a.m.Chicago O'Hare Intl
1h 51m
YYZ12:32 p.m.Toronto Pearson Intl
C$ 263
Find similar

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
28 Jan
YYZ5:30 p.m.Toronto Pearson Intl
2h 20m
ORD6:50 p.m.Chicago O'Hare Intl
2 Feb
ORD4:50 p.m.Chicago O'Hare Intl
1h 55m
YYZ7:45 p.m.Toronto Pearson Intl
C$ 259
Find similar
United Airlines
6 Feb
YYZ8:55 a.m.Toronto Pearson Intl
2h 06m
ORD10:01 a.m.Chicago O'Hare Intl
8 Feb
ORD1:00 p.m.Chicago O'Hare Intl
4h 57m
1 stop
YYZ6:57 p.m.Toronto Pearson Intl
C$ 325
Find similar
United Airlines
4 Nov
YYZ5:30 p.m.Toronto Pearson Intl
2h 09m
ORD6:39 p.m.Chicago O'Hare Intl
11 Nov
ORD1:19 p.m.Chicago O'Hare Intl
1h 43m
YYZ4:02 p.m.Toronto Pearson Intl
C$ 360
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 13 October 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 21/11

6:15 p.m.-10:56 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Tue 25/11

6:06 a.m.-11:54 a.m.

1 stop4h 48m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 28/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Mon 2/2

4:50 p.m.-7:45 p.m.

Nonstop1h 55m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

6:20 p.m.-7:20 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 3/12

1:16 p.m.-4:03 p.m.

Nonstop1h 47m

C$ 262

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 5/11

2:30 p.m.-7:25 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Sun 9/11

6:45 a.m.-2:48 p.m.

1 stop7h 03m

C$ 281

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/11

6:15 a.m.-12:28 p.m.

1 stop7h 13m

Chicago Midway

Sat 8/11

3:00 p.m.-11:18 p.m.

1 stop7h 18m

C$ 281

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/12

12:05 p.m.-1:01 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Sun 7/12

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

Nonstop1h 40m

C$ 322

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 6/2

8:55 a.m.-10:01 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 8/2

1:00 p.m.-6:57 p.m.

1 stop4h 57m

C$ 325

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/12

10:00 a.m.-2:55 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Sun 7/12

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

C$ 344

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 20/11

9:52 a.m.-4:24 p.m.

1 stop7h 32m

Chicago O'Hare Intl

Mon 24/11

7:20 a.m.-9:53 p.m.

2 stops13h 33m

C$ 356

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 8/11

6:20 a.m.-10:30 a.m.

1 stop5h 10m

Chicago Midway

Tue 11/11

9:41 a.m.-4:02 p.m.

1 stop5h 21m

C$ 371

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 336.

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$ 640. 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$ 1,122. 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$ 638. 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$ 1,085 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$ 408 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$ 273 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 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 October 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 35% 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$ 355

Fastest flight time

1h 54m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto Pearson Intl Airport in the past 72 hours is C$ 355. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is C$ 551.
The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 54m
Direct flights go from Toronto Pearson Intl Airport to Chicago every day.
There is 1 airport near Chicago: 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$ 225Free CancellationRating
8.0
379 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 265Free CancellationRating
7.1
10,286 reviews
Search Air Canada flights
American AirlinesPriceFrom C$ 271Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 283Free CancellationRating
7.4
8,973 reviews
Search United Airlines flights
WestJetPriceFrom C$ 382Free CancellationRating
7.2
3,124 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 7 flights/week on average for this route. A good Porter Airlines flight deal for Toronto Pearson Intl Airport to Chicago starts from C$ 161 round-trip, up to an average price of C$ 235. Our users have rated Porter Airlines at 8.0/10.

  • 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$ 202 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around C$ 304. United Airlines operates 78 flights to Chicago from Toronto Pearson Intl Airport in an average week. Users have rated it 7.4/10 across 8,973 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 12/11
Wed 19/11
By creating a price alert you accept our terms of use and privacy policy.

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