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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 2/19. 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.
7:00 am - 2:23 pmYYZ-ORD
8h 23m1 stop
3:16 pm - 11:53 pmORD-YYZ
7h 37m1 stop
Fri, Jan 10 - Mon, Jan 27
7:35 am - 2:48 pmYYZ-ORD
8h 13m1 stop
3:16 pm - 11:53 pmORD-YYZ
7h 37m1 stop
Thu, Jan 9 - Mon, Jan 27
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
$256American Airlines
Find Deal
Thu, Jan 23 - Sun, Jan 26
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:00 am - 11:45 amORD-YYZ
4h 45m1 stop
$265American Airlines
Find Deal
Thu, Jan 23 - Sun, Jan 26
11:31 am - 12:31 pmYYZ-ORD
2h 00mnonstop
3:00 pm - 5:35 pmORD-YYZ
1h 35mnonstop
$272British Airways
Find Deal
Tue, Feb 4 - Tue, Feb 11
4:44 pm - 5:44 pmYYZ-ORD
2h 00mnonstop
5:10 am - 11:10 amORD-YYZ
5h 00m1 stop
$277British Airways
Find Deal
Thu, Feb 13 - Sun, Feb 16
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
2:05 pm - 4:46 pmORD-YYZ
1h 41mnonstop
$288Air Canada
Find Deal
Wed, Jan 8 - Fri, Jan 31
8:00 am - 8:57 amYYZ-ORD
1h 57mnonstop
7:20 am - 1:41 pmORD-YYZ
5h 21m1 stop
$293Air Canada
Find Deal
Fri, Jan 24 - Mon, Jan 27
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
$300United Airlines
Find Deal
Sun, Jan 19 - Wed, Jan 22
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
8:50 am - 2:18 pmORD-YYZ
4h 28m1 stop
$304United Airlines
Find Deal
Tue, Jan 7 - Wed, Jan 8
7:00 am - 2:25 pmYYZ-ORD
8h 25m1 stop
Wed, Feb 19
8:35 am - 6:13 pmYYZ-ORD
10h 38m1 stop
Wed, Feb 19
1:14 pm - 2:14 pmYYZ-ORD
2h 00mnonstop
$152American Airlines
Find Deal
Tue, Jan 21
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$163American Airlines
Find Deal
Wed, Jan 15
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
$164United Airlines
Find Deal
Sun, Jan 19
5:05 pm - 10:36 pmYYZ-ORD
6h 31m1 stop
$167Delta
Find Deal
Tue, Jan 21
6:00 am - 12:55 pmYYZ-ORD
7h 55m1 stop
$169Delta
Find Deal
Sun, Jan 12
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
$174United Airlines
Find Deal
Sun, Jan 19
12:30 am - 8:00 amYYZ-ORD
8h 30m1 stop
$196Air Canada
Find Deal
Tue, Jan 21
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
$200Air Canada
Find Deal
Sun, Mar 30
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
3:00 pm - 5:35 pmORD-YYZ
1h 35mnonstop
$378American Airlines
Find Deal
Wed, Dec 25 - Sat, Jan 25
12:30 am - 8:03 amYYZ-ORD
8h 33m1 stop
2:05 pm - 4:46 pmORD-YYZ
1h 41mnonstop
$382Air Canada
Find Deal
Fri, Dec 27 - Fri, Jan 31
12:30 am - 8:03 amYYZ-ORD
8h 33m1 stop
7:20 am - 1:41 pmORD-YYZ
5h 21m1 stop
$387Air Canada
Find Deal
Fri, Dec 27 - Fri, Jan 31
11:40 am - 12:40 pmYYZ-ORD
2h 00mnonstop
7:00 am - 3:46 pmORD-YYZ
7h 46m1 stop
$388American Airlines
Find Deal
Wed, Dec 25 - Sat, Jan 25
5:15 pm - 4:40 pmYYZ-ORD
24h 25m1 stop
6:45 am - 10:52 pmORD-YYZ
15h 07m1 stop
$415WestJet
Find Deal
Thu, Dec 26 - Wed, Jan 29
6:35 pm - 7:32 pmYYZ-ORD
1h 57mnonstop
9:05 pm - 8:34 amORD-YYZ
10h 29m1 stop
$421United Airlines
Find Deal
Fri, Dec 27 - Mon, Dec 30
5:15 pm - 4:40 pmYYZ-ORD
24h 25m1 stop
6:15 am - 6:18 amORD-YYZ
23h 03m2 stops
$424WestJet
Find Deal
Thu, Dec 26 - Wed, Jan 29
1:00 pm - 4:10 pmYYZ-MDW
4h 10m1 stop
9:34 am - 5:31 pmMDW-YYZ
6h 57m1 stop
$424Delta
Find Deal
Wed, Dec 25 - Sat, Jan 25
7:40 pm - 11:25 pmYYZ-ORD
4h 45m1 stop
8:30 pm - 11:11 pmORD-YYZ
1h 41mnonstop
$427United Airlines
Find Deal
Fri, Dec 27 - Sat, Jan 4
5:15 pm - 8:59 pmYYZ-ORD
4h 44m1 stop
5:30 pm - 10:41 pmORD-YYZ
4h 11m1 stop
$560Delta
Find Deal
Mon, Dec 23 - Thu, Dec 26
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
$256American Airlines
Find Deal
Thu, Jan 23 - Sun, Jan 26
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$257American Airlines
Find Deal
Sat, Jan 18 - Sun, Feb 2
11:31 am - 12:31 pmYYZ-ORD
2h 00mnonstop
3:00 pm - 5:35 pmORD-YYZ
1h 35mnonstop
$272British Airways
Find Deal
Tue, Feb 4 - Tue, Feb 11
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$276American Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 28
11:31 am - 12:31 pmYYZ-ORD
2h 00mnonstop
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$278American Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
4:44 pm - 5:44 pmYYZ-ORD
2h 00mnonstop
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$282British Airways
Find Deal
Thu, Feb 13 - Sun, Feb 16
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
2:05 pm - 4:46 pmORD-YYZ
1h 41mnonstop
$288Air Canada
Find Deal
Wed, Jan 8 - Fri, Jan 31
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
4:51 pm - 7:45 pmORD-YYZ
1h 54mnonstop
$295United Airlines
Find Deal
Tue, Jan 7 - Wed, Jan 8
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
$300United Airlines
Find Deal
Sun, Jan 19 - Wed, Jan 22
9:00 pm - 10:13 pmYYZ-ORD
2h 13mnonstop
2:05 pm - 4:46 pmORD-YYZ
1h 41mnonstop
$301Air Canada
Find Deal
Mon, Jan 20 - Sun, Jan 26

British Airways flights from Toronto Pearson Intl Airport to Chicago

Our best British Airways deals on Toronto Pearson Intl Airport to Chicago flight tickets
British Airways
Feb 4
YYZ11:31 amToronto Pearson Intl
2h 00m
ORD12:31 pmChicago O'Hare Intl
Feb 11
ORD3:00 pmChicago O'Hare Intl
1h 35m
YYZ5:35 pmToronto Pearson Intl
British Airways
Feb 13
YYZ4:44 pmToronto Pearson Intl
2h 00m
ORD5:44 pmChicago O'Hare Intl
Feb 16
ORD5:10 amChicago O'Hare Intl
5h 00m
1 stop
YYZ11:10 amToronto Pearson Intl

Delta flights from Toronto Pearson Intl Airport to Chicago

Our best Delta deals on Toronto Pearson Intl Airport to Chicago flight tickets
Delta
Feb 13
YYZ10:10 amToronto Pearson Intl
3h 45m
1 stop
ORD12:55 pmChicago O'Hare Intl
Feb 15
ORD4:15 pmChicago O'Hare Intl
5h 52m
1 stop
YYZ11:07 pmToronto Pearson Intl
Delta
Feb 13
YYZ6:00 amToronto Pearson Intl
4h 16m
1 stop
ORD9:16 amChicago O'Hare Intl
Feb 16
ORD6:59 amChicago O'Hare Intl
8h 10m
1 stop
YYZ4:09 pmToronto Pearson Intl
Delta
Jan 8
YYZ6:00 amToronto Pearson Intl
4h 16m
1 stop
ORD9:16 amChicago O'Hare Intl
Jan 29
ORD10:05 amChicago O'Hare Intl
6h 09m
1 stop
YYZ5:14 pmToronto Pearson Intl

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 April is, on average, the cheapest month to fly to Chicago from Toronto Pearson Intl Airport, with most prices found around $239. If you’re not able to fly to Chicago in April, then February is your next best option. Flight prices from Toronto Pearson Intl Airport to Chicago during February average around $243.

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 Wednesday when prices can be found for as low as $258. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Pearson Intl Airport to Chicago for around $292.

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 $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $325.

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?

The best time to book a flight to Chicago from Toronto Pearson Intl Airport is 48 days out, which is when prices tend to be around $296. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $241.

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 December 2024, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 2% more expensive 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

$127

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 $127. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $238.
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 $204Free CancellationRating
7.0
8,413 reviews
Search Air Canada flights
United AirlinesPriceFrom $219Free CancellationRating
7.4
9,028 reviews
Search United Airlines flights
Porter AirlinesPriceFrom $221Free CancellationRating
7.9
282 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 64 flights on this route every week with an average price of $303. 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 17 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average American Airlines airfare for this route is around $325, 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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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