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Cheap flights from Toronto Pearson Intl Airport to Chicago from $99

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 11/1. 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

Air Canada Logo
12:05 pm - 1:01 pmYYZ-ORD
1h 56mnonstop
Air Canada Logo
3:55 pm - 6:34 pmORD-YYZ
1h 39mnonstop
$147Air Canada
Find Deal
Fri, Nov 7 - Sun, Nov 9
Air Canada Logo
4:00 pm - 8:11 pmYYZ-ORD
5h 11m1 stop
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
$157Air Canada
Find Deal
Sat, Sep 13 - Sat, Sep 20
United Airlines Logo
9:00 am - 9:55 amYYZ-ORD
1h 55mnonstop
United Airlines Logo
6:01 pm - 8:44 pmORD-YYZ
1h 43mnonstop
$172United Airlines
Find Deal
Sun, Oct 5 - Fri, Oct 17
United Airlines Logo
5:15 pm - 6:12 pmYYZ-ORD
1h 57mnonstop
United Airlines Logo
7:10 am - 9:58 amORD-YYZ
1h 48mnonstop
$177United Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
American Airlines Logo
6:30 am - 7:25 amYYZ-ORD
1h 55mnonstop
American Airlines Logo
12:33 pm - 10:29 pmORD-YYZ
8h 56m1 stop
$181American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Lufthansa Logo
5:15 pm - 6:12 pmYYZ-ORD
1h 57mnonstop
Lufthansa Logo
9:12 pm - 11:58 pmORD-YYZ
1h 46mnonstop
$182Lufthansa
Find Deal
Thu, Sep 4 - Sun, Sep 7
American Airlines Logo
7:20 am - 4:08 pmYYZ-ORD
9h 48m1 stop
American Airlines Logo
9:39 am - 12:32 pmORD-YYZ
1h 53mnonstop
$187American Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 24
Lufthansa Logo
5:15 pm - 6:12 pmYYZ-ORD
1h 57mnonstop
Lufthansa Logo
7:10 am - 9:58 amORD-YYZ
1h 48mnonstop
$191Lufthansa
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
6:30 am - 10:20 amYYZ-ORD
4h 50m1 stop
Delta Logo
5:00 pm - 10:56 pmORD-YYZ
4h 56m1 stop
$212Delta
Find Deal
Mon, Sep 1 - Sat, Sep 20
Delta Logo
4:11 pm - 8:23 pmYYZ-ORD
5h 12m1 stop
Delta Logo
9:10 am - 5:23 pmORD-YYZ
7h 13m1 stop
$217Delta
Find Deal
Wed, Aug 20 - Thu, Sep 4

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
Nov 7
YYZ12:05 pmToronto Pearson Intl
1h 56m
ORD1:01 pmChicago O'Hare Intl
Nov 9
ORD3:55 pmChicago O'Hare Intl
1h 39m
YYZ6:34 pmToronto Pearson Intl
$147
Find similar
Air Canada
Sep 13
YYZ4:00 pmToronto Pearson Intl
5h 11m
1 stop
ORD8:11 pmChicago O'Hare Intl
Sep 20
ORD8:25 pmChicago O'Hare Intl
1h 43m
YYZ11:08 pmToronto Pearson Intl
$157
Find similar
Air Canada
Sep 13
YYZ4:00 pmToronto Pearson Intl
5h 11m
1 stop
ORD8:11 pmChicago O'Hare Intl
Sep 20
ORD3:35 pmChicago O'Hare Intl
5h 04m
1 stop
YYZ9:39 pmToronto Pearson Intl
$161
Find similar

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

Our best Delta deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 1
YYZ6:30 amToronto Pearson Intl
4h 50m
1 stop
ORD10:20 amChicago O'Hare Intl
Sep 20
ORD5:00 pmChicago O'Hare Intl
4h 56m
1 stop
YYZ10:56 pmToronto Pearson Intl
$212
Find similar
Delta
Aug 20
YYZ4:11 pmToronto Pearson Intl
5h 12m
1 stop
ORD8:23 pmChicago O'Hare Intl
Sep 4
ORD9:10 amChicago O'Hare Intl
7h 13m
1 stop
YYZ5:23 pmToronto Pearson Intl
$217
Find similar
Delta
Aug 29
YYZ12:48 pmToronto Pearson Intl
5h 16m
1 stop
ORD5:04 pmChicago O'Hare Intl
Sep 26
ORD5:37 pmChicago O'Hare Intl
4h 43m
1 stop
YYZ11:20 pmToronto Pearson Intl
$224
Find similar

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 August 1, 2025.
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

Fri 11/7

12:05 pm-1:01 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 11/9

3:55 pm-6:34 pm

Nonstop1h 39m

$147

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 9/13

4:00 pm-8:11 pm

1 stop5h 11m

Chicago O'Hare Intl

Sat 9/20

8:25 pm-11:08 pm

Nonstop1h 43m

$157

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 10/5

9:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Fri 10/17

6:01 pm-8:44 pm

Nonstop1h 43m

$172

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/4

5:15 pm-6:12 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/7

7:10 am-9:58 am

Nonstop1h 48m

$177

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 9/13

6:30 am-7:25 am

Nonstop1h 55m

Chicago O'Hare Intl

Sat 9/20

12:33 pm-10:29 pm

1 stop8h 56m

$181

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/4

5:15 pm-6:12 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/7

9:12 pm-11:58 pm

Nonstop1h 46m

$182

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/3

7:20 am-4:08 pm

1 stop9h 48m

Chicago O'Hare Intl

Wed 9/24

9:39 am-12:32 pm

Nonstop1h 53m

$187

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/4

5:15 pm-6:12 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/7

7:10 am-9:58 am

Nonstop1h 48m

$191

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 9/1

6:30 am-10:20 am

1 stop4h 50m

Chicago O'Hare Intl

Sat 9/20

5:00 pm-10:56 pm

1 stop4h 56m

$212

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 8/20

4:11 pm-8:23 pm

1 stop5h 12m

Chicago O'Hare Intl

Thu 9/4

9:10 am-5:23 pm

1 stop7h 13m

$217

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of May 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 $434. 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 $708.

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 $375 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $597. 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 $296 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 $240 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 August 2025, prices for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights are approximately 34% 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

$99

Fastest flight time

1h 53m

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 $99. 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 $147.
The fastest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport takes 1h 53m
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 53m, 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 $155Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $211Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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

    Across 75 United Airlines flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $289, with the best United Airlines deals starting from $165 round-trip. 8,900 users have rated United Airlines on momondo, with an average score of 7.4/10.

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

    The best American Airlines deal for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $211, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $334 round-trip. American Airlines operates 27 flights out of Toronto Pearson Intl Airport into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 10,000 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

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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