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Cheap flights from Toronto to Chicago from $129

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 to Chicago departing on 10/15. 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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Cheap round-trip flights

Multiple Airlines Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Multiple Airlines Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
$196Multiple Airlines
Find Deal
Mon, Oct 20 - Thu, Oct 23
Multiple Airlines Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Multiple Airlines Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
$197Multiple Airlines
Find Deal
Mon, Oct 20 - Thu, Oct 23
Multiple Airlines Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Multiple Airlines Logo
7:43 pm - 2:05 pmORD-YYZ
17h 22m1 stop
$199Multiple Airlines
Find Deal
Mon, Oct 20 - Wed, Oct 22
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
Thu, Oct 16 - Thu, Oct 30
WestJet Logo
6:15 am - 9:12 amYYZ-ORD
3h 57m1 stop
WestJet Logo
10:30 am - 5:19 pmORD-YYZ
5h 49m1 stop
$236WestJet
Find Deal
Sat, Oct 18 - Sat, Oct 25
WestJet Logo
8:00 am - 4:43 pmYYZ-ORD
9h 43m1 stop
WestJet Logo
2:20 pm - 12:26 amORD-YYZ
9h 06m1 stop
$238WestJet
Find Deal
Thu, Oct 23 - Mon, Oct 27
Air Canada Logo
3:25 pm - 8:17 pmYTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 am - 2:45 pmORD-YTZ
5h 05m1 stop
$251Air Canada
Find Deal
Sat, Oct 18 - Sat, Oct 25
Air Canada Logo
3:25 pm - 8:06 pmYTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 am - 4:45 pmORD-YTZ
7h 05m1 stop
$265Air Canada
Find Deal
Sat, Oct 4 - Mon, Oct 6
Air Canada Logo
3:25 pm - 8:17 pmYTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 am - 4:45 pmORD-YTZ
7h 05m1 stop
$279Air Canada
Find Deal
Sat, Oct 18 - Mon, Oct 20
Air Canada Logo
3:25 pm - 8:17 pmYTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 am - 2:45 pmORD-YTZ
5h 05m1 stop
$291Air Canada
Find Deal
Sat, Oct 18 - Sun, Oct 19

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

Our best Air Canada deals on Toronto to Chicago O'Hare Intl Airport flight tickets
Air Canada
Oct 18
YTZ3:25 pmToronto Island
5h 52m
1 stop
ORD8:17 pmChicago O'Hare Intl
Oct 25
ORD8:40 amChicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 pmToronto Island
$251
Find similar
Air Canada
Oct 4
YTZ3:25 pmToronto Island
5h 41m
1 stop
ORD8:06 pmChicago O'Hare Intl
Oct 6
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
$265
Find similar
Air Canada
Oct 18
YTZ3:25 pmToronto Island
5h 52m
1 stop
ORD8:17 pmChicago O'Hare Intl
Oct 20
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
$279
Find similar

WestJet flights from Toronto to Chicago O'Hare Intl Airport

Our best WestJet deals on Toronto to Chicago O'Hare Intl Airport flight tickets
WestJet
Oct 16
YYZ6:30 amToronto Pearson Intl
11h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 30
ORD2:20 pmChicago O'Hare Intl
9h 06m
1 stop
YYZ12:26 amToronto Pearson Intl
$235
Find similar
WestJet
Oct 18
YYZ6:15 amToronto Pearson Intl
3h 57m
1 stop
ORD9:12 amChicago O'Hare Intl
Oct 25
ORD10:30 amChicago O'Hare Intl
5h 49m
1 stop
YYZ5:19 pmToronto Pearson Intl
$236
Find similar
WestJet
Oct 23
YYZ8:00 amToronto Pearson Intl
9h 43m
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
$238
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto 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 September 16, 2025.
Use the filters below to find and compare flights from Toronto 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

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

$196

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

Wed 10/22

7:43 pm-2:05 pm

1 stop17h 22m

$199

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/16

6:30 am-4:43 pm

1 stop11h 13m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-12:26 am

1 stop9h 06m

$235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/18

6:15 am-9:12 am

1 stop3h 57m

Chicago O'Hare Intl

Sat 10/25

10:30 am-5:19 pm

1 stop5h 49m

$236

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/23

8:00 am-4:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Mon 10/27

2:20 pm-12:26 am

1 stop9h 06m

$238

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/18

3:25 pm-8:17 pm

1 stop5h 52m

Chicago O'Hare Intl

Sat 10/25

8:40 am-2:45 pm

1 stop5h 05m

$251

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/4

3:25 pm-8:06 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 10/6

8:40 am-4:45 pm

1 stop7h 05m

$265

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/18

3:25 pm-8:17 pm

1 stop5h 52m

Chicago O'Hare Intl

Mon 10/20

8:40 am-4:45 pm

1 stop7h 05m

$279

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/18

3:25 pm-8:17 pm

1 stop5h 52m

Chicago O'Hare Intl

Sun 10/19

8:40 am-2:45 pm

1 stop5h 05m

$291

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 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 and Chicago O'Hare Intl Airport?

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

The month of November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around $274.

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 Saturday 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $701.

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 in the evening is the least expensive time of day to depart. momondo users have found prices as low as $396 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $613. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $292 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 for as low as $216 on momondo.

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

There are 4 cabin classes available to choose from on Toronto 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.

Can stopping save me money on Toronto to Chicago O'Hare Intl Airport flights?

You could potentially save up to 15% on your flight if you consider stops on a Toronto to Chicago O'Hare Intl Airport flight.

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

As of September 2025, prices for Toronto to Chicago O'Hare Intl Airport flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago O'Hare Intl Airport

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

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

Best Price Found

$245

Fastest flight time

1h 53m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Toronto in the past 72 hours is $245. The best round-trip flight deal from Toronto to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $374.
The fastest flight from Toronto to Chicago O'Hare Intl Airport takes 1h 53m
Direct flights go from Toronto to Chicago O'Hare Intl Airport every day.
Search flight deals

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

    There are 446.6 mi between Toronto and Chicago O'Hare Intl. A reasonable flight in good conditions will take 3h 57m.

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

    Prices for flights from Toronto to Chicago O'Hare Intl Airport are updated daily.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Chicago O'Hare Intl Airport.

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

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

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

Compare and see reviews for airlines that fly from Toronto to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $146Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
American AirlinesPriceFrom $196Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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

    The lowest priced United Airlines flight from Toronto to Chicago O'Hare Intl Airport from the last 72 hours was $165. Generally, United Airlines has 87 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 to Chicago O'Hare Intl Airport

    The best American Airlines deal for Toronto to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $196, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $341 round-trip. American Airlines operates 31 flights out of Toronto 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
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?

Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.

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?

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.

An easier way to manage your Chicago O'Hare Intl Airport trip

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