Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 194

YYZ — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in March or January, booked 82 days in advance, depart on a Friday or Saturday and return on a Friday

Cheap flight deals from Pearson Intl to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Pearson Intl to Chicago

Fri 20/118:00 a.m. -
1 stop8h 00m
Tue 24/1110:15 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 310
Fri 11/122:35 p.m. -
Nonstop2h 03m
Mon 14/1210:05 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 312
Mon 16/114:30 p.m. -
Nonstop2h 13m
Mon 16/118:40 p.m. -
Nonstop1h 43m
Deal found 26/10C$ 319
Thu 17/128:05 a.m. -
Nonstop2h 13m
Thu 31/124:30 p.m. -
Nonstop1h 40m
Deal found 27/10C$ 320
Sat 14/117:44 p.m. -
1 stop5h 17m
Sun 15/117:03 a.m. -
Nonstop1h 44m
Deal found 30/10C$ 327
Sat 12/122:45 p.m. -
1 stop9h 44m
Sun 13/1211:05 a.m. -
Nonstop1h 58m
Deal found 29/10C$ 329
Tue 1/1210:00 a.m. -
1 stop6h 02m
Fri 4/1210:05 a.m. -
Nonstop1h 37m
Deal found 26/10C$ 331
Thu 17/129:00 a.m. -
1 stop7h 02m
Fri 1/14:30 p.m. -
Nonstop1h 40m
Deal found 27/10C$ 333
Thu 3/121:22 p.m. -
Nonstop2h 20m
Wed 9/123:42 p.m. -
1 stop5h 02m
Deal found 27/10C$ 334
Mon 28/122:35 p.m. -
Nonstop2h 03m
Fri 1/18:50 p.m. -
Nonstop1h 42m
Deal found 27/10C$ 341
Fri 13/117:44 p.m. -
1 stop5h 17m
Sat 14/117:03 a.m. -
Nonstop1h 44m
Deal found 28/10C$ 345
Thu 19/119:45 a.m. -
1 stop4h 06m
Mon 23/119:30 a.m. -
1 stop3h 00m
Deal found 27/10C$ 364

Find flight deals from Pearson Intl to Chicago

Round-trip from

C$ 310

One-way from

C$ 194

Popular in

December

Cheapest in

March

Average price

C$ 453

Good round-trip deal

C$ 659 or less

Good one-way deal

C$ 382 or less
Air Canada
  • Air Canada
  • 20/11-24/11
  • 1 total stop
  • 9h 37m total
  • Toronto to Chicago
Air Canada
  • Air Canada
  • 26/11-31/12
  • 2 total stops
  • 7h 57m total
  • Toronto to Chicago
Highest demand for flights based on searches. 5% potential increase in price (C$ 33 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
Average for round-trip flights in October 2026
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).

Cheapflights Fare Finder

 
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

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 25/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 218

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 4/12

12:15 p.m.-6:26 p.m.

1 stop7h 11m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 24/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 26/11

6:00 a.m.-11:25 a.m.

1 stop6h 25m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 3/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 224
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 17/11

10:53 a.m.-11:57 a.m.

Nonstop2h 04m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 248

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

7:26 p.m.-8:48 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 259

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 25/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 259

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 28/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 260

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/12

7:26 p.m.-8:48 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 263

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

Showing 1-10 of 44 resultsSorted by cheapest first
1
2
3
...
5

Best time to book a flight from Pearson Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pearson Intl with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago

What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?

Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 375). Flying from Toronto Pearson Intl Airport to Chicago in December is currently the most expensive (average of C$ 487). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YYZ to CHI?

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight in the afternoon.

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago?

Airfare is below average for this route at the moment.
Toronto Pearson Intl Airport to Chicago flights typically cost between C$ 376 and C$ 548 in November.
The cheapest round-trip price found within the last 5 days was C$ 310 on Air Canada (20 Nov-24 Nov).

How often are flights from Toronto to Chicago delayed?

About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?

Booking 80 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Pearson Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago?

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Porter Airlines,United Airlines, andWestJet from Toronto Pearson Intl Airport to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Toronto Pearson Intl Airport to Chicago?

    Airlines like United Airlines and Delta fly from Toronto Pearson Intl Airport to Chicago in about 5h 14m. The time it takes to get you to your destination can typically vary by up to 03m. The distance between Toronto Pearson Intl Airport and Chicago is about 702 km. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago round-trip?

    Currently priced at C$ 263, American Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Air Canada - these airlines can fly you to your destination from C$ 300 and C$ 303, respectively. Users have found that American Airlines is 35% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago one-way?

    One-way options have recently been found by users for as low as C$ 158 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 165 and American Airlines from C$ 167 one-way.

  • What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago?

    Before booking your flight to Chicago from Toronto Pearson Intl Airport, check out the most reliable airlines to get you to your destination on time: Sun Country Air (100%), Copa Airlines (86%), Republic Airways( 82%).

  • What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?

    On average you can expect to pay C$ 1,322 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 272 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 340.

  • Can I find deals for flights from Pearson Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Chicago.

  • Can I find deals for business class flights from Pearson Intl to Chicago?

    Yes. Cheapflights offers flight deals from Pearson Intl to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 375). Flying from Toronto Pearson Intl Airport to Chicago in December is currently the most expensive (average of C$ 487). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Fly from Pearson Intl to Chicago on these airlines

Top 5 airlines flying from Pearson Intl to Chicago

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 263AverageC$ 473FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 300AverageC$ 420FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 303AverageC$ 456FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 305AverageC$ 519FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 387AverageC$ 496FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

How does Cheapflights help users find flights from Pearson Intl to Chicago?

Cheapflights makes it easy to find Pearson Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Pearson Intl to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Pearson Intl to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Pearson Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Pearson Intl to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.