How many flights depart from Toronto to Chicago O'Hare Intl Airport on average per week?

446 flights are operational weekly from Toronto to Chicago O'Hare Intl Airport as of May 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

What is the cheapest airline that flies from Toronto to Chicago O'Hare Intl?

United Airlines, Air Canada, and Delta are the most popular carriers operating from Toronto to Chicago O'Hare Intl

How long does it take to fly to Chicago O'Hare Intl Airport?

On average, it takes 1h 54m to fly from Toronto to Chicago O'Hare Intl Airport if you fly out of Toronto (the most popular airport in Toronto) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago O'Hare Intl Airport). If you’re flying out of Hamilton and into Chicago O'Hare Intl Airport, then the flight time is around 16h 41m.

How many flights depart from Toronto to Chicago O'Hare Intl Airport on average per day?

63 flights are operational daily from Toronto to Chicago O'Hare Intl Airport as of May 2026. The most popular departure time for this route is 1:00PM, with 46% of flights per day taking off in the afternoon.

What is the most punctual flight time for Toronto to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Which airline has the best punctuality record on Toronto to Chicago flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 8% of their flights experiencing any sort of delay.

What airlines fly to Chicago O'Hare Intl Airport?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Toronto according to our data. Air Canada is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

How often are flights from Toronto to Chicago delayed?

Historically, on average around 12% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 140 minutes.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

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

There are 4 operators available for flights from Toronto to Chicago O'Hare Intl Airport as of May 2026.

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.

$125 Cheap Flights from Toronto to Chicago O'Hare Intl Airport in 2026

Q: What is the typical price of a round-trip flight between Toronto and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route. Typical prices usually range from $368 to $228. The lowest price recently found on this route was $203.

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Find the cheapest flights from Toronto to Chicago

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:40 pm - 9:35 pm

YTZ

ORD

1h 55mnonstop

11:45 am - 2:25 pm

ORD

YTZ

1h 40mnonstop

$203Porter Airlines

Sun, Sep 6 - Sun, Sep 13

8:40 pm - 9:35 pm

YTZ

ORD

1h 55mnonstop

7:00 am - 9:40 am

ORD

YTZ

1h 40mnonstop

$204Porter Airlines

Sun, Sep 13 - Sat, Sep 19

10:05 am - 11:00 am

YTZ

ORD

1h 55mnonstop

7:00 am - 9:40 am

ORD

YTZ

1h 40mnonstop

$205Porter Airlines

Sat, Sep 19 - Tue, Sep 22

11:00 am - 12:00 pm

YYZ

ORD

2h 00mnonstop

9:20 pm - 11:59 pm

ORD

YYZ

1h 39mnonstop

$206United Airlines

Tue, Jun 2 - Tue, Jun 9

4:00 pm - 4:59 pm

YYZ

ORD

1h 59mnonstop

9:55 am - 12:35 pm

ORD

YYZ

1h 40mnonstop

$207Air Canada

Fri, May 22 - Tue, May 26

8:30 am - 2:53 pm

YTZ

ORD

7h 23m

1 stop

7:25 am - 10:06 am

ORD

YTZ

1h 41mnonstop

$207Air Canada

Sat, May 23 - Wed, Jun 3

8:50 am - 9:50 am

YYZ

ORD

2h 00mnonstop

7:09 am - 9:54 am

ORD

YYZ

1h 45mnonstop

$208United Airlines

Fri, May 22 - Fri, May 29

12:25 pm - 1:22 pm

YYZ

ORD

1h 57mnonstop

9:50 am - 12:35 pm

ORD

YYZ

1h 45mnonstop

$217GOL

Sat, Aug 22 - Sun, Aug 23

8:15 am - 11:15 pm

YHM

ORD

16h 00m

1 stop

5:05 am - 3:55 pm

ORD

YHM

9h 50m

1 stop

$425Multiple Airlines

Sat, May 23 - Mon, May 25

8:15 am - 11:15 pm

YHM

ORD

16h 00m

1 stop

5:05 am - 3:55 pm

ORD

YHM

9h 50m

1 stop

$441Multiple Airlines

Sat, May 23 - Mon, May 25

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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

May 22

YYZ4:00 pmToronto Pearson Intl

1h 59m

ORD4:59 pmChicago O'Hare Intl

May 26

ORD9:55 amChicago O'Hare Intl

1h 40m

YYZ12:35 pmToronto Pearson Intl

$207

Air Canada

May 14

YYZ8:00 amToronto Pearson Intl

2h 00m

ORD9:00 amChicago O'Hare Intl

May 16

ORD9:55 amChicago O'Hare Intl

1h 40m

YYZ12:35 pmToronto Pearson Intl

$209

Air Canada

May 28

YYZ12:25 pmToronto Pearson Intl

2h 00m

ORD1:25 pmChicago O'Hare Intl

Jun 1

ORD9:15 pmChicago O'Hare Intl

1h 44m

YYZ11:59 pmToronto Pearson Intl

$211

Porter Airlines flights from Toronto to Chicago O'Hare Intl Airport

Our best Porter Airlines deals on Toronto to Chicago O'Hare Intl Airport flight tickets

Porter Airlines

Sep 6

YTZ8:40 pmToronto Island

1h 55m

ORD9:35 pmChicago O'Hare Intl

Sep 13

ORD11:45 amChicago O'Hare Intl

1h 40m

YTZ2:25 pmToronto Island

$203

Porter Airlines

Sep 13

YTZ8:40 pmToronto Island

1h 55m

ORD9:35 pmChicago O'Hare Intl

Sep 19

ORD7:00 amChicago O'Hare Intl

1h 40m

YTZ9:40 amToronto Island

$204

Porter Airlines

Sep 19

YTZ10:05 amToronto Island

1h 55m

ORD11:00 amChicago O'Hare Intl

Sep 22

ORD7:00 amChicago O'Hare Intl

1h 40m

YTZ9:40 amToronto Island

$205

momondo Fare Finder

Use the filters below to find and compare flights from Toronto to Chicago O'Hare Intl Airport that are best for you.

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 9/6

8:40 pm-9:35 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 9/13

11:45 am-2:25 pm

Nonstop1h 40m

$203

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 9/13

8:40 pm-9:35 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sat 9/19

7:00 am-9:40 am

Nonstop1h 40m

$204

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 9/19

10:05 am-11:00 am

Nonstop1h 55m

Chicago O'Hare Intl

Tue 9/22

7:00 am-9:40 am

Nonstop1h 40m

$205

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/2

11:00 am-12:00 pm

Nonstop2h 00m

Chicago O'Hare Intl

Tue 6/9

9:20 pm-11:59 pm

Nonstop1h 39m

$206

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 5/22

4:00 pm-4:59 pm

Nonstop1h 59m

Chicago O'Hare Intl

Tue 5/26

9:55 am-12:35 pm

Nonstop1h 40m

$207

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 5/23

8:30 am-2:53 pm

1 stop7h 23m

Chicago O'Hare Intl

Wed 6/3

7:25 am-10:06 am

Nonstop1h 41m

$207

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 5/22

8:50 am-9:50 am

Nonstop2h 00m

Chicago O'Hare Intl

Fri 5/29

7:09 am-9:54 am

Nonstop1h 45m

$208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 8/22

12:25 pm-1:22 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 8/23

9:50 am-12:35 pm

Nonstop1h 45m

$217

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 5/23

8:15 am-11:15 pm

1 stop16h 00m

Chicago O'Hare Intl

Mon 5/25

5:05 am-3:55 pm

1 stop9h 50m

$425

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 5/23

8:15 am-11:15 pm

1 stop16h 00m

Chicago O'Hare Intl

Mon 5/25

5:05 am-3:55 pm

1 stop9h 50m

$441

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Delays

Other information

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around $60.

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 $467. 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 $750.

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 $405 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $713. 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 Island to Chicago O'Hare Intl for the best Toronto - Chicago O'Hare Intl flight prices

How far in advance should I book a flight from Toronto 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 $295 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 $195 on momondo.

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

No. A direct flight is the cheapest option for a flight between Toronto to Chicago O'Hare Intl Airport.

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

As of May 2026, prices for Toronto to Chicago O'Hare Intl Airport flights are approximately 14% 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	$94
Fastest flight time	1h 50m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Toronto in the past 72 hours is $94. The best round-trip flight deal from Toronto to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $190.

The fastest flight from Toronto to Chicago O'Hare Intl Airport takes 1h 50m

Direct flights go from Toronto to Chicago O'Hare Intl Airport every day.

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Frequently asked questions about flying from Toronto to Chicago O'Hare Intl Airport

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 1h 50m.
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?
There are 4 operators available for flights from Toronto to Chicago O'Hare Intl Airport as of May 2026.
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?
Based on momondo bookings for flights between Toronto and Chicago O'Hare Intl Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 11.75% of the total bookings. Other popular models include Boeing 737 MAX 8 with 11.30%, Embraer 175 (Enhanced Winglets) with 10.66%, and Embraer 195 E2 with 8.01%.
What is the most popular airline from Toronto to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Toronto to Chicago O'Hare Intl Airport is Air Canada, representing 59% of all bookings. The subsequent popular airlines are United Airlines at 27% and American Airlines at 14%.

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 Canada	PriceFrom $146	Free Cancellation	Rating 7.1 10,996 reviews	Search Air Canada flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 9,681 reviews	Search United Airlines flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.1 11,670 reviews	Search American Airlines flights
Porter Airlines	PriceFrom $192	Free Cancellation	Rating 8.0 436 reviews	Search Porter Airlines flights

Porter Airlines Flights From Toronto to Chicago O'Hare Intl Airport
The lowest priced Porter Airlines flight from Toronto to Chicago O'Hare Intl Airport from the last 72 hours was $192. Generally, Porter Airlines has 32 flights on this route every week with an average price of $411. Porter Airlines is rated 8.0/10 by our users.
United Airlines Flights From Toronto to Chicago O'Hare Intl Airport
The best United Airlines deal for Toronto 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 $267 round-trip. United Airlines operates 77 flights out of Toronto into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,681 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

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Orland Park

Oak Brook

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Janesville

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Hammond

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Elgin

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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.

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Cheap flights from Toronto to Chicago from $125

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 6/6. 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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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

Porter Airlines flights from Toronto to Chicago O'Hare Intl Airport

Our best Porter Airlines deals on Toronto to Chicago O'Hare Intl Airport flight tickets

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Use the filters below to find and compare flights from Toronto to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto to Chicago O'Hare Intl Airport

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?

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

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

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

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

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

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

What is the cheapest airline that flies from Toronto to Chicago O'Hare Intl?

What airlines fly to Chicago O'Hare Intl Airport?

How often are flights from Toronto to Chicago delayed?

What is the most punctual flight time for Toronto to Chicago flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Toronto to Chicago flights?

How many flights depart from Toronto to Chicago O'Hare Intl Airport on average per day?

How many flights depart from Toronto to Chicago O'Hare Intl Airport on average per week?

How long does it take to fly to Chicago O'Hare Intl Airport?

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

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

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Frequently asked questions about flying 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

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

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

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