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Cheap flights from Toronto Pearson Intl Airport to Chicago from $127

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 12/3. 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.
United Airlines Logo
9:00 pm - 10:05 pmYYZ-ORD
2h 05mnonstop
United Airlines Logo
6:28 pm - 9:21 pmORD-YYZ
1h 53mnonstop
$184United Airlines
Find Deal
Sun, Jan 11 - Fri, Jan 16
United Airlines Logo
9:00 am - 10:06 amYYZ-ORD
2h 06mnonstop
United Airlines Logo
6:28 pm - 9:21 pmORD-YYZ
1h 53mnonstop
$185United Airlines
Find Deal
Thu, Jan 8 - Sun, Jan 11
Air Canada Logo
4:50 pm - 5:48 pmYYZ-ORD
1h 58mnonstop
Air Canada Logo
8:30 pm - 11:09 pmORD-YYZ
1h 39mnonstop
$186Air Canada
Find Deal
Mon, Dec 29 - Mon, Jan 5
United Airlines Logo
9:00 pm - 10:04 pmYYZ-ORD
2h 04mnonstop
United Airlines Logo
6:25 pm - 11:46 pmORD-YYZ
4h 21m1 stop
$188United Airlines
Find Deal
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
6:00 am - 7:15 amYYZ-ORD
2h 15mnonstop
American Airlines Logo
5:00 am - 11:02 amORD-YYZ
5h 02m1 stop
$190American Airlines
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Thu, Dec 4 - Sun, Dec 7
Air Canada Logo
9:00 pm - 10:05 pmYYZ-ORD
2h 05mnonstop
Air Canada Logo
8:30 pm - 11:09 pmORD-YYZ
1h 39mnonstop
$192Air Canada
Find Deal
Mon, Dec 29 - Mon, Jan 5
American Airlines Logo
4:44 pm - 5:44 pmYYZ-ORD
2h 00mnonstop
American Airlines Logo
11:51 am - 7:00 pmORD-YYZ
6h 09m1 stop
$193American Airlines
Find Deal
Wed, Jan 7 - Wed, Jan 14
Air Canada Logo
4:50 pm - 5:48 pmYYZ-ORD
1h 58mnonstop
Air Canada Logo
8:15 pm - 10:54 pmORD-YYZ
1h 39mnonstop
$199Air Canada
Find Deal
Wed, Dec 3 - Sat, Dec 6
Delta Logo
12:13 pm - 4:22 pmYYZ-ORD
5h 09m1 stop
Delta Logo
8:55 am - 5:15 pmORD-YYZ
7h 20m1 stop
$201Delta
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Sun, Dec 14 - Tue, Dec 16
Delta Logo
6:00 am - 8:52 amYYZ-MDW
3h 52m1 stop
Delta Logo
6:30 pm - 10:41 pmMDW-YYZ
3h 11m1 stop
$210Delta
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Thu, Jan 8 - Sun, Jan 11

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
Jan 11
YYZ9:00 pmToronto Pearson Intl
2h 05m
ORD10:05 pmChicago O'Hare Intl
Jan 16
ORD6:28 pmChicago O'Hare Intl
1h 53m
YYZ9:21 pmToronto Pearson Intl
$184
Find similar
United Airlines
Jan 8
YYZ9:00 amToronto Pearson Intl
2h 06m
ORD10:06 amChicago O'Hare Intl
Jan 11
ORD6:28 pmChicago O'Hare Intl
1h 53m
YYZ9:21 pmToronto Pearson Intl
$185
Find similar
United Airlines
Feb 13
YYZ9:00 pmToronto Pearson Intl
2h 04m
ORD10:04 pmChicago O'Hare Intl
Feb 17
ORD6:25 pmChicago O'Hare Intl
4h 21m
1 stop
YYZ11:46 pmToronto Pearson Intl
$188
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
Dec 29
YYZ4:50 pmToronto Pearson Intl
1h 58m
ORD5:48 pmChicago O'Hare Intl
Jan 5
ORD8:30 pmChicago O'Hare Intl
1h 39m
YYZ11:09 pmToronto Pearson Intl
$186
Find similar
Air Canada
Dec 29
YYZ9:00 pmToronto Pearson Intl
2h 05m
ORD10:05 pmChicago O'Hare Intl
Jan 5
ORD8:30 pmChicago O'Hare Intl
1h 39m
YYZ11:09 pmToronto Pearson Intl
$192
Find similar
Air Canada
Dec 3
YYZ4:50 pmToronto Pearson Intl
1h 58m
ORD5:48 pmChicago O'Hare Intl
Dec 6
ORD8:15 pmChicago O'Hare Intl
1h 39m
YYZ10:54 pmToronto Pearson Intl
$199
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 832,500 searches. Data last updated November 16, 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

Sun 1/11

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Fri 1/16

6:28 pm-9:21 pm

Nonstop1h 53m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/8

9:00 am-10:06 am

Nonstop2h 06m

Chicago O'Hare Intl

Sun 1/11

6:28 pm-9:21 pm

Nonstop1h 53m

$185

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 12/29

4:50 pm-5:48 pm

Nonstop1h 58m

Chicago O'Hare Intl

Mon 1/5

8:30 pm-11:09 pm

Nonstop1h 39m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/13

9:00 pm-10:04 pm

Nonstop2h 04m

Chicago O'Hare Intl

Tue 2/17

6:25 pm-11:46 pm

1 stop4h 21m

$188

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/4

6:00 am-7:15 am

Nonstop2h 15m

Chicago O'Hare Intl

Sun 12/7

5:00 am-11:02 am

1 stop5h 02m

$190

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 12/29

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Mon 1/5

8:30 pm-11:09 pm

Nonstop1h 39m

$192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/7

4:44 pm-5:44 pm

Nonstop2h 00m

Chicago O'Hare Intl

Wed 1/14

11:51 am-7:00 pm

1 stop6h 09m

$193

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/3

4:50 pm-5:48 pm

Nonstop1h 58m

Chicago O'Hare Intl

Sat 12/6

8:15 pm-10:54 pm

Nonstop1h 39m

$199

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/14

12:13 pm-4:22 pm

1 stop5h 09m

Chicago O'Hare Intl

Tue 12/16

8:55 am-5:15 pm

1 stop7h 20m

$201

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 1/8

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sun 1/11

6:30 pm-10:41 pm

1 stop3h 11m

$210

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 September is, on average, the cheapest month to fly to Chicago from Toronto Pearson Intl Airport, with most prices found around $231. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Toronto Pearson Intl Airport to Chicago during August average around $238.

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 $412. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Pearson Intl Airport to Chicago for around $692.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto Pearson Intl Airport to Chicago during this time can be as low as $431. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $586.

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 $293 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 $195 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?

No. A direct flight is the cheapest option for a flight between Toronto Pearson Intl Airport to Chicago.

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

As of November 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 12% 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

$197

Fastest flight time

1h 55m

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 $197. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $427.
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 is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

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

    The straight-line distance from Toronto Pearson Intl to Chicago is 424.4 mi. Typically, this will take 1h 55m by plane in normal conditions.

  • 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 that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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
Air CanadaPriceFrom $146Free CancellationRating
7.1
10,454 reviews
Search Air Canada flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
9,016 reviews
Search United Airlines flights
Porter AirlinesPriceFrom $180Free CancellationRating
8.0
392 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $196Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
WestJetPriceFrom $208Free CancellationRating
7.2
3,162 reviews
Search WestJet flights

  • Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago

    The lowest priced Porter Airlines flight from Toronto Pearson Intl Airport to Chicago from the last 72 hours was $180. Generally, Porter Airlines has 31 flights on this route every week with an average price of $423. Porter Airlines is rated 8.0/10 by our users.

  • United Airlines Flights From Toronto Pearson Intl Airport to Chicago

    United Airlines (7.4/10 from 9,016 reviews) operates around 69 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average United Airlines airfare for this route is around $288, with deals from around $165 rare but found on momondo. Referenced prices are for round-trip Toronto Pearson Intl Airport to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Chicago for you.

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?

momondo helps you find the best flight between Toronto and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport