How many flights depart from Toronto to Chicago on average per week?

As of December 2025, 395 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

How many flights depart from Toronto to Chicago on average per day?

The number of flights available between Toronto and Chicago is 56 per day as of December 2025. The most frequent departure time is 11:00AM, with 47% of daily flights leaving at noon.

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 6% of their flights experiencing any sort of delay.

What airlines fly to Chicago?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Toronto according to our data. Air Canada is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago 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 11% 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 139 minutes.

How long does it take to fly to Chicago?

Average flight duration from Toronto to Chicago depends on which airport you fly into and out of. Flying from Toronto to Chicago O'Hare Intl Airport is 1h 54m on average, while flying from Hamilton to Chicago O'Hare Intl Airport is 8h 21m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

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

What is the cheapest airline that flies from Toronto to Chicago?

Lufthansa, Air Canada, and Porter Airlines are the most popular carriers operating from Toronto to Chicago

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.

When did momondo last update prices for flights from Toronto to Chicago?

Prices for flights from Toronto to Chicago are updated daily.

How many operators does momondo search for flights from Toronto to Chicago?

As of December 2025, there are 4 operators available to choose from for flights from Toronto to Chicago.

How old do you have to be to fly from Toronto 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 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.

$117 Cheap Flights from Toronto to Chicago in 2025/26

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9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$178Porter Airlines

Thu, Jan 22 - Thu, Jan 29

12:15 pm - 9:03 pm

YYZ

ORD

33h 48m3 stops

7:20 am - 11:20 pm

ORD

YYZ

15h 00m1 stop

$179Multiple Airlines

Sun, Jan 25 - Wed, Jan 28

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$179Porter Airlines

Fri, Feb 20 - Mon, Feb 23

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$180Porter Airlines

Fri, Feb 20 - Mon, Feb 23

9:00 am - 2:55 pm

YYZ

ORD

6h 55m1 stop

8:40 pm - 11:19 pm

ORD

YYZ

1h 39mnonstop

$181Air Canada

Thu, Jan 29 - Sun, Feb 1

10:30 am - 5:42 pm

YYZ

ORD

8h 12m1 stop

6:00 am - 11:59 am

ORD

YYZ

4h 59m1 stop

$184American Airlines

Fri, Feb 6 - Sun, Feb 8

4:50 pm - 5:48 pm

YYZ

ORD

1h 58mnonstop

2:00 pm - 4:39 pm

ORD

YYZ

1h 39mnonstop

$185Air Canada

Fri, Feb 13 - Sun, Feb 15

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

1:26 pm - 10:44 pm

MDW

YYZ

8h 18m1 stop

$212Delta

Thu, Feb 5 - Sun, Feb 8

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

9:53 am - 3:59 pm

MDW

YYZ

5h 06m1 stop

$213Delta

Sun, Feb 1 - Wed, Feb 4

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

9:50 am - 3:59 pm

MDW

YYZ

5h 09m1 stop

$260WestJet

Tue, Jan 6 - Tue, Jan 13

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets

Air Canada

Jan 29

YYZ9:00 amToronto Pearson Intl

6h 55m

1 stop

ORD2:55 pmChicago O'Hare Intl

Feb 1

ORD8:40 pmChicago O'Hare Intl

1h 39m

YYZ11:19 pmToronto Pearson Intl

$181

Find similar

Air Canada

Feb 13

YYZ4:50 pmToronto Pearson Intl

1h 58m

ORD5:48 pmChicago O'Hare Intl

Feb 15

ORD2:00 pmChicago O'Hare Intl

1h 39m

YYZ4:39 pmToronto Pearson Intl

$185

Find similar

Air Canada

Jan 24

YYZ9:00 amToronto Pearson Intl

6h 55m

1 stop

ORD2:55 pmChicago O'Hare Intl

Feb 1

ORD8:40 pmChicago O'Hare Intl

1h 39m

YYZ11:19 pmToronto Pearson Intl

$187

Find similar

American Airlines flights from Toronto to Chicago

Our best American Airlines deals on Toronto to Chicago flight tickets

American Airlines

Feb 6

YYZ10:30 amToronto Pearson Intl

8h 12m

1 stop

ORD5:42 pmChicago O'Hare Intl

Feb 8

ORD6:00 amChicago O'Hare Intl

4h 59m

1 stop

YYZ11:59 amToronto Pearson Intl

$184

Find similar

American Airlines

Feb 2

YYZ7:04 pmToronto Pearson Intl

2h 00m

ORD8:04 pmChicago O'Hare Intl

Feb 18

ORD9:43 amChicago O'Hare Intl

5h 52m

1 stop

YYZ4:35 pmToronto Pearson Intl

$194

Find similar

American Airlines

Feb 13

YYZ7:10 pmToronto Pearson Intl

5h 43m

1 stop

ORD11:53 pmChicago O'Hare Intl

Feb 15

ORD9:47 amChicago O'Hare Intl

1h 45m

YYZ12:32 pmToronto Pearson Intl

$200

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Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/22

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$178

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/25

12:15 pm-9:03 pm

3 stops33h 48m

Chicago O'Hare Intl

Wed 1/28

7:20 am-11:20 pm

1 stop15h 00m

$179

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$179

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$180

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/29

9:00 am-2:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Sun 2/1

8:40 pm-11:19 pm

Nonstop1h 39m

$181

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/6

10:30 am-5:42 pm

1 stop8h 12m

Chicago O'Hare Intl

Sun 2/8

6:00 am-11:59 am

1 stop4h 59m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/13

4:50 pm-5:48 pm

Nonstop1h 58m

Chicago O'Hare Intl

Sun 2/15

2:00 pm-4:39 pm

Nonstop1h 39m

$185

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sun 2/8

1:26 pm-10:44 pm

1 stop8h 18m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 2/1

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Wed 2/4

9:53 am-3:59 pm

1 stop5h 06m

$213

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 1/6

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Tue 1/13

9:50 am-3:59 pm

1 stop5h 09m

$260

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How to get the cheapest flight ticket from Toronto 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

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Toronto to Chicago during June average around $225.

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 Friday when prices can be found for as low as $411. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto to Chicago for around $700.

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 to Chicago during this time can be as low as $399. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $585.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $291 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as $195 on momondo.

What cabin class options are available on Toronto to Chicago flights?

There are 4 cabin classes available to choose from on Toronto 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 to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

How have Toronto to Chicago flight prices changed over time?

As of December 2025, prices for Toronto to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Best Price Found	$116
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Toronto in the past 72 hours is $116. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is $183.

The fastest flight from Toronto to Chicago takes 1h 49m

Direct flights go from Toronto to Chicago every day.

There are 3 airports in Chicago. From Toronto there are direct flights to Chicago Midway (MDW).

Search flight deals

How far is Toronto to Chicago by plane?
There are 435.3 mi between Toronto and Chicago. Flights usually cover this in 1h 49m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Toronto to Chicago?
Prices for flights from Toronto to Chicago are updated daily.
How many operators does momondo search for flights from Toronto to Chicago?
As of December 2025, there are 4 operators available to choose from for flights from Toronto to Chicago.
How old do you have to be to fly from Toronto 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 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 to Chicago?
Based on momondo bookings for flights between Toronto and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 15.56% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 11.54%, Boeing 737-800 with 10.46%, and Boeing 737 MAX 8 with 9.77%.
What is the most popular airline from Toronto to Chicago?
momondo data reveals that the most frequently booked airline on the route from Toronto to Chicago is Porter Airlines, representing 55% of all bookings. The subsequent popular airlines are Air Canada at 25%, United Airlines at 11%, and American Airlines at 7%.

Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $149	Free Cancellation	Rating 7.1 10,517 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $158	Free Cancellation	Rating 8.0 398 reviews	Search Porter Airlines flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights
American Airlines	PriceFrom $195	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights

Porter Airlines Flights From Toronto to Chicago
Porter Airlines flies from Toronto to Chicago around 40 times per week, with 398 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Toronto to Chicago in the last 72 hours was $158 (round-trip), much lower than the average airfare cost of $340 for Porter Airlines flights on this route.
United Airlines Flights From Toronto to Chicago
United Airlines (7.4/10 from 9,095 reviews) operates around 70 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $282, with deals from around $165 rare but found on momondo. Referenced prices are for round-trip Toronto to Chicago flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Toronto to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.

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Cheap flights from Toronto to Chicago from $117

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 2/22. 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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How to get the cheapest flight ticket from Toronto to Chicago

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Toronto to Chicago during June average around $225.

What is the cheapest day to depart on your flight to Chicago?

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 to Chicago during this time can be as low as $399. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $585.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Toronto to Chicago flights?

There are 4 cabin classes available to choose from on Toronto 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 to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

How have Toronto to Chicago flight prices changed over time?

As of December 2025, prices for Toronto to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Toronto to Chicago?

Lufthansa, Air Canada, and Porter Airlines are the most popular carriers operating from Toronto to Chicago

What airlines fly to Chicago?

How often are flights from Toronto to Chicago delayed?

Historically, on average around 11% 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 139 minutes.

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.

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

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

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 6% of their flights experiencing any sort of delay.

How many flights depart from Toronto to Chicago on average per day?

The number of flights available between Toronto and Chicago is 56 per day as of December 2025. The most frequent departure time is 11:00AM, with 47% of daily flights leaving at noon.

How many flights depart from Toronto to Chicago on average per week?

As of December 2025, 395 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

When to book flights from Toronto to Chicago

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Toronto to Chicago by plane?

When did momondo last update prices for flights from Toronto to Chicago?

How many operators does momondo search for flights from Toronto to Chicago?

How old do you have to be to fly from Toronto to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Toronto to Chicago?

What is the most popular airline from Toronto to Chicago?

Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo

Porter Airlines Flights From Toronto to Chicago

United Airlines Flights From Toronto to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down