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Cheap flights from Toronto Pearson Intl Airport to Chicago from $42

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 2/12. 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

These are some of the best round-trip flight deals from Toronto Pearson Intl Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto Pearson Intl Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from Toronto Pearson Intl Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Toronto Pearson Intl Airport to Chicago

Find recent round-trip train or bus tickets from Toronto Pearson Intl Airport to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
9:00 pm - 10:13 pmYYZ-ORD
2h 13mnonstop
4:51 pm - 7:45 pmORD-YYZ
1h 54mnonstop
$227United Airlines
Find Deal
Wed, Dec 25 - Mon, Jan 6
3:30 pm - 4:30 pmYYZ-ORD
2h 00mnonstop
12:51 pm - 3:45 pmORD-YYZ
1h 54mnonstop
$231Air Canada
Find Deal
Tue, Dec 10 - Wed, Dec 25
6:40 pm - 7:37 pmYYZ-ORD
1h 57mnonstop
8:30 pm - 11:11 pmORD-YYZ
1h 41mnonstop
$232Air Canada
Find Deal
Mon, Jan 6 - Mon, Feb 3
9:00 pm - 10:13 pmYYZ-ORD
2h 13mnonstop
4:00 pm - 10:15 pmORD-YYZ
5h 15m1 stop
$237United Airlines
Find Deal
Wed, Dec 25 - Mon, Jan 6
6:00 am - 12:50 pmYYZ-MDW
7h 50m1 stop
4:50 pm - 11:08 pmMDW-YYZ
5h 18m1 stop
$261Delta
Find Deal
Tue, Dec 10 - Wed, Dec 25
6:00 am - 8:54 amYYZ-MDW
3h 54m1 stop
5:05 pm - 10:52 pmMDW-YYZ
4h 47m1 stop
$262Delta
Find Deal
Wed, Jan 29 - Sat, Feb 8
4:44 pm - 5:44 pmYYZ-ORD
2h 00mnonstop
4:45 pm - 10:35 pmORD-YYZ
4h 50m1 stop
$274American Airlines
Find Deal
Wed, Dec 4 - Fri, Dec 6
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:34 pm - 9:29 pmORD-YYZ
1h 55mnonstop
$275American Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
6:30 am - 1:35 pmYYZ-MDW
8h 05m1 stop
7:14 pm - 1:41 pmMDW-YYZ
17h 27m1 stop
$301WestJet
Find Deal
Tue, Dec 3 - Fri, Dec 6
6:30 am - 6:32 pmYYZ-MDW
13h 02m1 stop
12:44 pm - 7:06 pmMDW-YYZ
5h 22m1 stop
$304WestJet
Find Deal
Sat, Dec 7 - Tue, Dec 10
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
$42Air Canada
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Wed, Feb 12
6:40 pm - 7:37 pmYYZ-ORD
1h 57mnonstop
$43Air Canada
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Wed, Feb 12
9:00 am - 10:05 amYYZ-ORD
2h 05mnonstop
$144United Airlines
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Sat, Dec 7
12:20 pm - 6:38 pmYYZ-ORD
7h 18m1 stop
$145United Airlines
Find Deal
Tue, Jan 7
10:00 am - 9:07 pmYYZ-ORD
12h 07m1 stop
Tue, Dec 10
7:30 am - 8:15 pmYYZ-ORD
13h 45m1 stop
Wed, Dec 4
10:10 am - 1:08 pmYYZ-MDW
3h 58m1 stop
$158Delta
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Mon, Jan 13
10:10 am - 1:08 pmYYZ-MDW
3h 58m1 stop
$159Delta
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Mon, Jan 6
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$164American Airlines
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Fri, Nov 22
7:35 am - 3:08 pmYYZ-ORD
8h 33m1 stop
$171American Airlines
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Sat, Jan 4
7:45 am - 8:15 pmYYZ-ORD
13h 30m2 stops
7:44 am - 3:56 pmORD-YYZ
7h 12m1 stop
Sat, Nov 9 - Sat, Nov 16
6:30 am - 4:49 pmYYZ-ORD
11h 19m1 stop
10:50 am - 9:09 amORD-YYZ
21h 19m1 stop
$403WestJet
Find Deal
Sat, Nov 9 - Sat, Nov 16
1:10 pm - 2:10 pmYYZ-ORD
2h 00mnonstop
6:34 pm - 9:24 pmORD-YYZ
1h 50mnonstop
$448American Airlines
Find Deal
Thu, Nov 7 - Sat, Nov 16
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
9:50 am - 12:30 pmORD-YYZ
1h 40mnonstop
$449American Airlines
Find Deal
Fri, Nov 8 - Tue, Nov 12
3:30 pm - 4:29 pmYYZ-ORD
1h 59mnonstop
7:28 am - 12:46 pmORD-YYZ
4h 18m1 stop
$467Air Canada
Find Deal
Fri, Nov 8 - Wed, Nov 13
3:30 pm - 4:30 pmYYZ-ORD
2h 00mnonstop
4:52 pm - 7:45 pmORD-YYZ
1h 53mnonstop
$469United Airlines
Find Deal
Sat, Nov 9 - Tue, Nov 12
6:52 am - 8:05 amYYZ-ORD
2h 13mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$471Air Canada
Find Deal
Fri, Nov 8 - Sun, Nov 10
4:30 pm - 8:14 pmYYZ-ORD
4h 44m1 stop
8:50 am - 4:06 pmORD-YYZ
6h 16m1 stop
$474United Airlines
Find Deal
Thu, Nov 7 - Sat, Nov 16
6:00 am - 8:55 amYYZ-MDW
3h 55m1 stop
9:35 am - 6:28 pmMDW-YYZ
7h 53m1 stop
$522Delta
Find Deal
Sat, Nov 9 - Sun, Nov 10
6:00 am - 1:16 pmYYZ-ORD
8h 16m1 stop
7:05 am - 11:29 amORD-YYZ
3h 24m1 stop
$552Delta
Find Deal
Wed, Nov 6 - Sat, Nov 9
9:00 pm - 10:13 pmYYZ-ORD
2h 13mnonstop
8:30 pm - 11:11 pmORD-YYZ
1h 41mnonstop
$227Air Canada
Find Deal
Wed, Dec 25 - Mon, Jan 6
3:30 pm - 4:30 pmYYZ-ORD
2h 00mnonstop
12:51 pm - 3:45 pmORD-YYZ
1h 54mnonstop
$231Air Canada
Find Deal
Tue, Dec 10 - Wed, Dec 25
6:40 pm - 7:37 pmYYZ-ORD
1h 57mnonstop
8:30 pm - 11:11 pmORD-YYZ
1h 41mnonstop
$232Air Canada
Find Deal
Mon, Jan 6 - Mon, Feb 3
9:00 pm - 10:13 pmYYZ-ORD
2h 13mnonstop
10:53 am - 1:42 pmORD-YYZ
1h 49mnonstop
$234United Airlines
Find Deal
Tue, Dec 24 - Wed, Jan 1
9:00 pm - 10:07 pmYYZ-ORD
2h 07mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$252Lufthansa
Find Deal
Thu, Nov 28 - Mon, Dec 2
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:34 pm - 9:29 pmORD-YYZ
1h 55mnonstop
Thu, Nov 28 - Mon, Dec 2
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$262United Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
3:00 pm - 5:35 pmORD-YYZ
1h 35mnonstop
$274American Airlines
Find Deal
Sun, Dec 8 - Sun, Dec 8
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:34 pm - 9:29 pmORD-YYZ
1h 55mnonstop
$285American Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
Thu, Dec 19 - Sun, Feb 9

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 10
YYZ3:30 pmToronto Pearson Intl
2h 00m
ORD4:30 pmChicago O'Hare Intl
Dec 25
ORD12:51 pmChicago O'Hare Intl
1h 54m
YYZ3:45 pmToronto Pearson Intl
Air Canada
Jan 6
YYZ6:40 pmToronto Pearson Intl
1h 57m
ORD7:37 pmChicago O'Hare Intl
Feb 3
ORD8:30 pmChicago O'Hare Intl
1h 41m
YYZ11:11 pmToronto Pearson Intl
Air Canada
Dec 10
YYZ6:25 amToronto Pearson Intl
5h 29m
1 stop
ORD10:54 amChicago O'Hare Intl
Dec 25
ORD12:51 pmChicago O'Hare Intl
1h 54m
YYZ3:45 pmToronto Pearson Intl

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
Dec 4
YYZ4:44 pmToronto Pearson Intl
2h 00m
ORD5:44 pmChicago O'Hare Intl
Dec 6
ORD4:45 pmChicago O'Hare Intl
4h 50m
1 stop
YYZ10:35 pmToronto Pearson Intl
American Airlines
Nov 28
YYZ6:15 amToronto Pearson Intl
2h 15m
ORD7:30 amChicago O'Hare Intl
Dec 2
ORD6:34 pmChicago O'Hare Intl
1h 55m
YYZ9:29 pmToronto Pearson Intl
American Airlines
Nov 28
YYZ6:15 amToronto Pearson Intl
2h 15m
ORD7:30 amChicago O'Hare Intl
Dec 2
ORD6:34 pmChicago O'Hare Intl
1h 55m
YYZ9:29 pmToronto Pearson Intl

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 from Toronto Pearson Intl Airport to Chicago?

January. The cheapest time of year to fly to Chicago from Toronto Pearson Intl Airport is January. Most expensive is November

What is the cheapest day to depart Toronto Pearson Intl Airport for Chicago?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Friday

When is the cheapest time to fly from Toronto Pearson Intl Airport to Chicago?

In the morning. Toronto Pearson Intl Airport to Chicago flights are approximately 16% more expensive in the evening than in the morning

What is the cheapest airline that flies to Chicago from Toronto Pearson Intl Airport?

Porter Airlines. Porter Airlines, Air Canada, and United Airlines are the most popular carriers operating from Toronto Pearson Intl Airport to Chicago

How far in advance should you book Toronto Pearson Intl Airport to Chicago flights?

38 days before. The cheapest time to buy a flight from Toronto Pearson Intl Airport to Chicago is approximately 38 days to departure

How many flights depart from Toronto Pearson Intl Airport to Chicago on average per day?

The number of flights available between Toronto Pearson Intl Airport and Chicago is 34 per day as of November 2024. The most frequent departure time is 3:00PM, with 46% of daily flights leaving at noon.

How many flights depart from Toronto Pearson Intl Airport to Chicago on average per week?

The number of flights available between Toronto Pearson Intl Airport and Chicago is 239 per week as of November 2024. The most frequent departure day is Tuesday, with 18% of weekly flights leaving on this day.

What cabin class options are available on Toronto Pearson Intl Airport to Chicago flights?

There are 4 cabin classes available to choose from on Toronto Pearson Intl Airport 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 2024, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 5% 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

$42

Fastest flight time

1h 51m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto Pearson Intl Airport in the past 72 hours is $42. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $227.
The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 51m
Direct flights go from Toronto Pearson Intl Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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 51m 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 $207Free CancellationRating
7.0
8,130 reviews
Search Air Canada flights
United AirlinesPriceFrom $219Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
Porter AirlinesPriceFrom $221Free CancellationRating
7.8
292 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $236Free 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 $219. Generally, United Airlines has 62 flights on this route every week with an average price of $290. 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 2 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average American Airlines airfare for this route is around $326, with deals from around $236 rare but found on momondo. Referenced prices are for round-trip Toronto Pearson Intl Airport to Chicago flight searches in the last 72 hours.


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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago