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Cheap flights from Toronto Pearson Intl Airport to Chicago from $122

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 4/26. 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.
Air Canada Logo
2:15 pm - 3:10 pm
YYZ
-
ORD
1h 55mnonstop
Air Canada Logo
8:00 am - 10:40 am
ORD
-
YYZ
1h 40mnonstop
$187Air Canada
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
6:45 am - 8:00 am
YYZ
-
ORD
2h 15mnonstop
United Airlines Logo
7:04 am - 9:54 am
ORD
-
YYZ
1h 50mnonstop
$189United Airlines
Thu, Mar 26 - Sun, Mar 29
United Airlines Logo
3:30 pm - 4:39 pm
YYZ
-
ORD
2h 09mnonstop
United Airlines Logo
6:28 pm - 9:21 pm
ORD
-
YYZ
1h 53mnonstop
$190United Airlines
Thu, Feb 19 - Mon, Feb 23
Lufthansa Logo
8:45 am - 9:50 am
YYZ
-
ORD
2h 05mnonstop
Lufthansa Logo
6:28 pm - 9:21 pm
ORD
-
YYZ
1h 53mnonstop
$192Lufthansa
Thu, Feb 19 - Mon, Feb 23
Air Canada Logo
8:00 am - 2:55 pm
YYZ
-
ORD
7h 55m
1 stop
Air Canada Logo
10:00 am - 12:40 pm
ORD
-
YYZ
1h 40mnonstop
$193Air Canada
Thu, Feb 19 - Mon, Feb 23
Air Canada Logo
4:00 pm - 8:10 pm
YYZ
-
ORD
5h 10m
1 stop
Air Canada Logo
10:00 am - 12:40 pm
ORD
-
YYZ
1h 40mnonstop
$196Air Canada
Sat, Feb 21 - Tue, Feb 24
Lufthansa Logo
3:30 pm - 4:39 pm
YYZ
-
ORD
2h 09mnonstop
Lufthansa Logo
6:28 pm - 9:21 pm
ORD
-
YYZ
1h 53mnonstop
$198Lufthansa
Thu, Feb 19 - Mon, Feb 23
Air Canada Logo
7:00 am - 11:18 am
YYZ
-
ORD
5h 18m
1 stop
Air Canada Logo
2:00 pm - 4:42 pm
ORD
-
YYZ
1h 42mnonstop
$199Air Canada
Thu, Mar 26 - Sun, Mar 29
American Airlines Logo
6:00 am - 7:15 am
YYZ
-
ORD
2h 15mnonstop
American Airlines Logo
6:08 am - 11:51 am
ORD
-
YYZ
4h 43m
1 stop
$200American Airlines
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
7:40 pm - 11:21 pm
YYZ
-
ORD
4h 41m
1 stop
United Airlines Logo
7:08 am - 9:53 am
ORD
-
YYZ
1h 45mnonstop
$204United Airlines
Tue, Jun 2 - Sat, Jun 6

Lufthansa flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Our best Lufthansa deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets
Lufthansa
Feb 19
YYZ3:30 pmToronto Pearson Intl
2h 09m
ORD4:39 pmChicago O'Hare Intl
Feb 23
ORD6:28 pmChicago O'Hare Intl
1h 53m
YYZ9:21 pmToronto Pearson Intl
$198
Lufthansa
Feb 19
YYZ8:45 amToronto Pearson Intl
2h 05m
ORD9:50 amChicago O'Hare Intl
Feb 23
ORD6:28 pmChicago O'Hare Intl
1h 53m
YYZ9:21 pmToronto Pearson Intl
$213
Lufthansa
Jan 31
YYZ9:00 amToronto Pearson Intl
2h 06m
ORD10:06 amChicago O'Hare Intl
Jan 31
ORD6:28 pmChicago O'Hare Intl
1h 53m
YYZ9:21 pmToronto Pearson Intl
$291

Air Canada flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Our best Air Canada deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets
Air Canada
Feb 19
YYZ2:15 pmToronto Pearson Intl
1h 55m
ORD3:10 pmChicago O'Hare Intl
Feb 23
ORD8:00 amChicago O'Hare Intl
1h 40m
YYZ10:40 amToronto Pearson Intl
$187
Air Canada
Feb 19
YYZ8:00 amToronto Pearson Intl
7h 55m
1 stop
ORD2:55 pmChicago O'Hare Intl
Feb 23
ORD10:00 amChicago O'Hare Intl
1h 40m
YYZ12:40 pmToronto Pearson Intl
$193
Air Canada
Feb 21
YYZ4:00 pmToronto Pearson Intl
5h 10m
1 stop
ORD8:10 pmChicago O'Hare Intl
Feb 24
ORD10:00 amChicago O'Hare Intl
1h 40m
YYZ12:40 pmToronto Pearson Intl
$196

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 January 28, 2026.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/19

2:15 pm-3:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 2/23

8:00 am-10:40 am

Nonstop1h 40m

$187

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 3/26

6:45 am-8:00 am

Nonstop2h 15m

Chicago O'Hare Intl

Sun 3/29

7:04 am-9:54 am

Nonstop1h 50m

$189

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/19

3:30 pm-4:39 pm

Nonstop2h 09m

Chicago O'Hare Intl

Mon 2/23

6:28 pm-9:21 pm

Nonstop1h 53m

$190

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/19

8:45 am-9:50 am

Nonstop2h 05m

Chicago O'Hare Intl

Mon 2/23

6:28 pm-9:21 pm

Nonstop1h 53m

$192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/19

8:00 am-2:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Mon 2/23

10:00 am-12:40 pm

Nonstop1h 40m

$193

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 2/21

4:00 pm-8:10 pm

1 stop5h 10m

Chicago O'Hare Intl

Tue 2/24

10:00 am-12:40 pm

Nonstop1h 40m

$196

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/19

3:30 pm-4:39 pm

Nonstop2h 09m

Chicago O'Hare Intl

Mon 2/23

6:28 pm-9:21 pm

Nonstop1h 53m

$198

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 3/26

7:00 am-11:18 am

1 stop5h 18m

Chicago O'Hare Intl

Sun 3/29

2:00 pm-4:42 pm

Nonstop1h 42m

$199

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/19

6:00 am-7:15 am

Nonstop2h 15m

Chicago O'Hare Intl

Mon 2/23

6:08 am-11:51 am

1 stop4h 43m

$200

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/2

7:40 pm-11:21 pm

1 stop4h 41m

Chicago O'Hare Intl

Sat 6/6

7:08 am-9:53 am

Nonstop1h 45m

$204

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto Pearson Intl Airport averaging around $253.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $458. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto Pearson Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $724.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $372 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $680. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Toronto Pearson Intl to Chicago O'Hare Intl flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $286 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport for as low as $195 on momondo.

What cabin class options are available on Toronto Pearson Intl to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Toronto Pearson Intl to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of January 2026, prices for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (YYZ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Best Price Found

$217

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the past 72 hours is $217. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $313.
The fastest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport takes 1h 55m
Direct flights go from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport every day.
Search flight deals

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

    Chicago O'Hare Intl is 435.5 mi away from Toronto Pearson Intl. Flights usually cover this in 1h 55m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

  • What is the most popular airline from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

Best airlines flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $140Free CancellationRating
7.1
10,666 reviews
Search Air Canada flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
9,209 reviews
Search United Airlines flights
Porter AirlinesPriceFrom $180Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
11,201 reviews
Search American Airlines flights

  • Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

    Across 31 Porter Airlines flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $420, with the best Porter Airlines deals starting from $180 round-trip. 412 users have rated Porter Airlines on momondo, with an average score of 7.9/10.

  • United Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

    The best United Airlines deal for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $165, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $279 round-trip. United Airlines operates 67 flights out of Toronto Pearson Intl Airport into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,209 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Schaumburg
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Naperville
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South Holland

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Toronto to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Toronto which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Toronto to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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