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Cheap flights from Toronto Pearson Intl Airport to Chicago from $128

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 10/20. 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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0 bags

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Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
$197
Find Deal
Mon, Oct 20 - Thu, Oct 23
Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Logo
7:06 pm - 9:07 pmORD-YYZ
25h 01m1 stop
$204
Find Deal
Mon, Oct 20 - Thu, Oct 30
Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Logo
7:20 pm - 9:07 pmORD-YYZ
24h 47m1 stop
$212
Find Deal
Mon, Oct 13 - Fri, Oct 24
Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
$213
Find Deal
Mon, Oct 13 - Thu, Oct 23
Logo
4:00 pm - 3:49 pmYYZ-ORD
24h 49m1 stop
Logo
7:20 pm - 9:07 pmORD-YYZ
24h 47m1 stop
$214
Find Deal
Sun, Oct 19 - Fri, Oct 24
WestJet Logo
6:30 am - 4:43 pmYYZ-ORD
11h 13m1 stop
WestJet Logo
2:20 pm - 12:26 amORD-YYZ
9h 06m1 stop
$235WestJet
Find Deal
Fri, Oct 24 - Mon, Oct 27
WestJet Logo
8:00 am - 4:43 pmYYZ-ORD
9h 43m1 stop
WestJet Logo
2:20 pm - 12:26 amORD-YYZ
9h 06m1 stop
$242WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 26
WestJet Logo
8:00 am - 4:43 pmYYZ-ORD
9h 43m1 stop
WestJet Logo
5:30 pm - 6:47 amORD-YYZ
12h 17m2 stops
$243WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
Delta Logo
12:15 pm - 6:25 pmYYZ-MDW
7h 10m1 stop
Delta Logo
9:35 am - 5:19 pmMDW-YYZ
6h 44m1 stop
$302Delta
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Wed, Oct 8 - Sun, Oct 12
Delta Logo
9:45 am - 12:28 pmYYZ-MDW
3h 43m1 stop
Delta Logo
9:35 am - 5:19 pmMDW-YYZ
6h 44m1 stop
$303Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27

WestJet flights from Toronto Pearson Intl Airport to Chicago

Our best WestJet deals on Toronto Pearson Intl Airport to Chicago flight tickets
WestJet
Oct 24
YYZ6:30 amToronto Pearson Intl
11h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 27
ORD2:20 pmChicago O'Hare Intl
9h 06m
1 stop
YYZ12:26 amToronto Pearson Intl
$235
Find similar
WestJet
Oct 17
YYZ8:00 amToronto Pearson Intl
9h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 26
ORD2:20 pmChicago O'Hare Intl
9h 06m
1 stop
YYZ12:26 amToronto Pearson Intl
$242
Find similar
WestJet
Oct 17
YYZ8:00 amToronto Pearson Intl
9h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 19
ORD5:30 pmChicago O'Hare Intl
12h 17m
2 stops
YYZ6:47 amToronto Pearson Intl
$243
Find similar

Delta flights from Toronto Pearson Intl Airport to Chicago

Our best Delta deals on Toronto Pearson Intl Airport to Chicago flight tickets
Delta
Oct 8
YYZ12:15 pmToronto Pearson Intl
7h 10m
1 stop
MDW6:25 pmChicago Midway
Oct 12
MDW9:35 amChicago Midway
6h 44m
1 stop
YYZ5:19 pmToronto Pearson Intl
$302
Find similar
Delta
Oct 23
YYZ9:45 amToronto Pearson Intl
3h 43m
1 stop
MDW12:28 pmChicago Midway
Oct 27
MDW9:35 amChicago Midway
6h 44m
1 stop
YYZ5:19 pmToronto Pearson Intl
$303
Find similar
Delta
Sep 27
YYZ6:00 amToronto Pearson Intl
8h 03m
1 stop
MDW1:03 pmChicago Midway
Oct 6
MDW1:48 pmChicago Midway
8h 30m
1 stop
YYZ11:18 pmToronto Pearson Intl
$375
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 September 13, 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

Mon 10/20

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Thu 10/23

12:53 pm-9:07 pm

1 stop7h 14m

$197

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/20

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Thu 10/30

7:06 pm-9:07 pm

1 stop25h 01m

$204

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/13

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Fri 10/24

7:20 pm-9:07 pm

1 stop24h 47m

$212

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/13

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Thu 10/23

12:53 pm-9:07 pm

1 stop7h 14m

$213

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 10/19

4:00 pm-3:49 pm

1 stop24h 49m

Chicago O'Hare Intl

Fri 10/24

7:20 pm-9:07 pm

1 stop24h 47m

$214

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/24

6:30 am-4:43 pm

1 stop11h 13m

Chicago O'Hare Intl

Mon 10/27

2:20 pm-12:26 am

1 stop9h 06m

$235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/17

8:00 am-4:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-12:26 am

1 stop9h 06m

$242

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/17

8:00 am-4:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-6:47 am

2 stops12h 17m

$243

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/8

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

Sun 10/12

9:35 am-5:19 pm

1 stop6h 44m

$302

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/23

9:45 am-12:28 pm

1 stop3h 43m

Chicago Midway

Mon 10/27

9:35 am-5:19 pm

1 stop6h 44m

$303

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 typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago?

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Toronto Pearson Intl Airport, with most prices found around $240. If you’re not able to fly to Chicago in August, then May is your next best option. Flight prices from Toronto Pearson Intl Airport to Chicago during May average around $253.

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 $395. 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 $639.

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 $387. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $578.

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 $295 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 $239 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 September 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 16% 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

$260

Fastest flight time

1h 53m

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 $260. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $390.
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 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 3h 14m 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 $145Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
8,934 reviews
Search United Airlines flights
American AirlinesPriceFrom $196Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • United Airlines Flights From Toronto Pearson Intl Airport to Chicago

    The lowest priced United Airlines flight from Toronto Pearson Intl Airport to Chicago from the last 72 hours was $165. Generally, United Airlines has 89 flights on this route every week with an average price of $286. United Airlines is rated 7.4/10 by our users.

  • American Airlines Flights From Toronto Pearson Intl Airport to Chicago

    American Airlines (7.2/10 from 10,000 reviews) operates around 32 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average American Airlines airfare for this route is around $340, with deals from around $196 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
Lansing
Portage
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