How often are flights from Toronto to Chicago delayed?

Historically, on average around 21% 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 41 minutes.

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

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

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

Monday 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.

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

According to our data, Air Canada have had the least number of delays on this route over the last 12 months; with about 67% of their flights experiencing any sort of delay.

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

Delta is the most popular carrier operating from Toronto Pearson Intl to Chicago Midway

How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago Midway 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 Midway Airport.

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

The required travel and health documents for your Chicago Midway 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 Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$135 Cheap Flights from Toronto Pearson Intl Airport to Chicago Midway Airport in 2025/26

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6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

1:26 pm - 7:08 pm

MDW

YYZ

4h 42m1 stop

$204Delta

Tue, Feb 3 - Tue, Feb 10

7:45 am - 12:46 pm

YYZ

MDW

6h 01m1 stop

1:26 pm - 7:08 pm

MDW

YYZ

4h 42m1 stop

$214Delta

Thu, Feb 5 - Sun, Feb 8

10:05 am - 5:37 pm

YYZ

MDW

8h 32m1 stop

9:50 am - 3:59 pm

MDW

YYZ

5h 09m1 stop

$231Delta

Fri, Feb 13 - Thu, Feb 26

6:00 am - 12:48 pm

YYZ

MDW

7h 48m1 stop

9:50 am - 3:59 pm

MDW

YYZ

5h 09m1 stop

$247Delta

Wed, Jan 7 - Fri, Jan 9

6:30 am - 1:09 pm

YYZ

MDW

7h 39m1 stop

1:28 pm - 10:41 pm

MDW

YYZ

8h 13m1 stop

$248Delta

Wed, Jan 14 - Fri, Jan 16

2:15 pm - 5:54 pm

YYZ

MDW

4h 39m1 stop

9:26 am - 6:32 pm

MDW

YYZ

8h 06m1 stop

$270Delta

Thu, Apr 23 - Mon, May 4

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

9:32 am - 4:12 pm

MDW

YYZ

5h 40m1 stop

$273WestJet

Fri, Jan 16 - Sun, Jan 18

6:15 am - 8:54 am

YYZ

MDW

3h 39m1 stop

1:49 pm - 11:11 pm

MDW

YYZ

8h 22m1 stop

$274WestJet

Fri, Feb 13 - Tue, Feb 17

6:10 am - 8:54 am

YYZ

MDW

3h 44m1 stop

9:34 am - 4:10 pm

MDW

YYZ

5h 36m1 stop

$275WestJet

Mon, Feb 16 - Thu, Feb 19

12:15 pm - 5:54 pm

YYZ

MDW

6h 39m1 stop

9:35 am - 3:08 pm

MDW

YYZ

4h 33m1 stop

$276WestJet

Sun, Mar 22 - Thu, Mar 26

WestJet flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Our best WestJet deals on Toronto Pearson Intl Airport to Chicago Midway Airport flight tickets

WestJet

Jan 16

YYZ6:00 amToronto Pearson Intl

3h 52m

1 stop

MDW8:52 amChicago Midway

Jan 18

MDW9:32 amChicago Midway

5h 40m

1 stop

YYZ4:12 pmToronto Pearson Intl

$273

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WestJet

Feb 13

YYZ6:15 amToronto Pearson Intl

3h 39m

1 stop

MDW8:54 amChicago Midway

Feb 17

MDW1:49 pmChicago Midway

8h 22m

1 stop

YYZ11:11 pmToronto Pearson Intl

$274

Find similar

WestJet

Feb 16

YYZ6:10 amToronto Pearson Intl

3h 44m

1 stop

MDW8:54 amChicago Midway

Feb 19

MDW9:34 amChicago Midway

5h 36m

1 stop

YYZ4:10 pmToronto Pearson Intl

$275

Find similar

Delta flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Our best Delta deals on Toronto Pearson Intl Airport to Chicago Midway Airport flight tickets

Delta

Feb 3

YYZ6:00 amToronto Pearson Intl

3h 52m

1 stop

MDW8:52 amChicago Midway

Feb 10

MDW1:26 pmChicago Midway

4h 42m

1 stop

YYZ7:08 pmToronto Pearson Intl

$204

Find similar

Delta

Feb 5

YYZ7:45 amToronto Pearson Intl

6h 01m

1 stop

MDW12:46 pmChicago Midway

Feb 8

MDW1:26 pmChicago Midway

4h 42m

1 stop

YYZ7:08 pmToronto Pearson Intl

$214

Find similar

Delta

Feb 13

YYZ10:05 amToronto Pearson Intl

8h 32m

1 stop

MDW5:37 pmChicago Midway

Feb 26

MDW9:50 amChicago Midway

5h 09m

1 stop

YYZ3:59 pmToronto Pearson Intl

$231

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momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 2/3

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Tue 2/10

1:26 pm-7:08 pm

1 stop4h 42m

$204

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

7:45 am-12:46 pm

1 stop6h 01m

Chicago Midway

Sun 2/8

1:26 pm-7:08 pm

1 stop4h 42m

$214

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 2/13

10:05 am-5:37 pm

1 stop8h 32m

Chicago Midway

Thu 2/26

9:50 am-3:59 pm

1 stop5h 09m

$231

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 1/7

6:00 am-12:48 pm

1 stop7h 48m

Chicago Midway

Fri 1/9

9:50 am-3:59 pm

1 stop5h 09m

$247

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 1/14

6:30 am-1:09 pm

1 stop7h 39m

Chicago Midway

Fri 1/16

1:28 pm-10:41 pm

1 stop8h 13m

$248

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/23

2:15 pm-5:54 pm

1 stop4h 39m

Chicago Midway

Mon 5/4

9:26 am-6:32 pm

1 stop8h 06m

$270

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 1/16

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sun 1/18

9:32 am-4:12 pm

1 stop5h 40m

$273

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 2/13

6:15 am-8:54 am

1 stop3h 39m

Chicago Midway

Tue 2/17

1:49 pm-11:11 pm

1 stop8h 22m

$274

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 2/16

6:10 am-8:54 am

1 stop3h 44m

Chicago Midway

Thu 2/19

9:34 am-4:10 pm

1 stop5h 36m

$275

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 3/22

12:15 pm-5:54 pm

1 stop6h 39m

Chicago Midway

Thu 3/26

9:35 am-3:08 pm

1 stop4h 33m

$276

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 Pearson Intl Airport to Chicago Midway 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

What is the cheapest month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto Pearson Intl Airport, with most prices found around $214. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Toronto Pearson Intl Airport during the month November is also very affordable. Most momondo users find prices during this month for around $217.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Toronto Pearson Intl Airport. The lowest ticket price found for a Wednesday departure recently was $208. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday 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 $291.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Toronto Pearson Intl Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $236 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $327. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Toronto Pearson Intl Airport to Chicago Midway Airport

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

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

Fastest flight time	3h 33m
Direct flights	None

The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 33m

There are no direct flights from Toronto Pearson Intl Airport to Chicago Midway Airport. There are no popular flight routes from Toronto Pearson Intl Airport to Chicago Midway Airport.

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How far is Toronto Pearson Intl to Chicago Midway by plane?
The straight-line distance from Toronto Pearson Intl to Chicago Midway is 432.2 mi. 3h 33m is a normal flight duration for this route.
When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago Midway Airport?
Prices for flights from Toronto Pearson Intl Airport to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago Midway 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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway 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 Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

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?

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Toronto to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Toronto Pearson Intl Airport to Chicago from $135

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WestJet flights from Toronto Pearson Intl Airport to Chicago Midway Airport

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Delta flights from Toronto Pearson Intl Airport to Chicago Midway Airport

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

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How to get the cheapest flight ticket from Toronto Pearson Intl Airport to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

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

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

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

Delta is the most popular carrier operating from Toronto Pearson Intl to Chicago Midway

How often are flights from Toronto to Chicago delayed?

Historically, on average around 21% 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 41 minutes.

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

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

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

Monday 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.

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

According to our data, Air Canada have had the least number of delays on this route over the last 12 months; with about 67% of their flights experiencing any sort of delay.

When to book flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Cheap Toronto Pearson Intl Airport to Chicago Midway Airport (YYZ to MDW) flight deals and tips

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

Fastest flight time

Direct flights

How far is Toronto Pearson Intl to Chicago Midway by plane?

When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago Midway Airport?

How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

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

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 Midway Airport 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

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo