How often are flights from Toronto to Chicago delayed?

Historically, on average around 15% 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 108 minutes.

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

Porter Airlines, Air Transat, and Delta are the most popular carriers operating from Toronto to Chicago Midway

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.

How long does it take to fly to Chicago Midway Airport?

On average, it takes 1h 55m to fly from Toronto to Chicago Midway 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 Midway Airport). If you’re flying out of Hamilton and into Chicago O'Hare Intl Airport, then the flight time is around 11h 56m.

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. Sunday 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, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

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

As of January 2026, there are 6 flights per week flying from Toronto to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 33% of flights taking off on this day.

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

As of January 2026, there is 1 operator available to choose from for flights from Toronto to Chicago Midway Airport.

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

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

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$110 Cheap Flights from Toronto to Chicago Midway Airport in 2026

Q: What is the typical price of a round-trip flight between Toronto and Chicago Midway Airport?

Prices are currently typical for flights on this route. Typical prices usually range from $186 to $224. The lowest price recently found on this route was $191.

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One-way

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Enter your travel dates to find the best prices.

9:20 am - 10:10 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$191Porter Airlines

Mon, Feb 9 - Fri, Feb 27

9:20 am - 10:10 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$196Porter Airlines

Thu, Feb 5 - Tue, Feb 10

9:20 am - 10:10 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$198Air Transat

Wed, Feb 18 - Wed, Feb 25

9:20 am - 10:10 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$200Multiple Airlines

Wed, Feb 18 - Wed, Feb 25

9:20 am - 10:10 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$201Air Transat

Thu, Feb 19 - Thu, Feb 26

11:05 am - 11:55 am

YTZ

MDW

1h 50mnonstop

4:15 pm - 6:57 pm

MDW

YTZ

1h 42mnonstop

$202Porter Airlines

Sat, Feb 14 - Mon, Feb 16

11:05 am - 11:55 am

YTZ

MDW

1h 50mnonstop

4:15 pm - 6:57 pm

MDW

YTZ

1h 42mnonstop

$203Porter Airlines

Sat, Feb 21 - Sun, Feb 22

7:45 am - 12:46 pm

YYZ

MDW

6h 01m

1 stop

9:50 am - 3:59 pm

MDW

YYZ

5h 09m

1 stop

$224Delta

Mon, Feb 9 - Thu, Feb 12

6:15 am - 12:46 pm

YYZ

MDW

7h 31m

1 stop

1:28 pm - 10:40 pm

MDW

YYZ

8h 12m

1 stop

$225Delta

Thu, Feb 19 - Thu, Feb 26

10:05 am - 12:29 pm

YYZ

MDW

3h 24m

1 stop

9:30 am - 11:06 pm

MDW

YYZ

12h 36m

1 stop

$279WestJet

Tue, Mar 24 - Fri, Mar 27

Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets

Porter Airlines

Feb 9

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Feb 27

MDW11:05 amChicago Midway

1h 42m

YTZ1:47 pmToronto Island

$191

Porter Airlines

Feb 5

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Feb 10

MDW11:05 amChicago Midway

1h 42m

YTZ1:47 pmToronto Island

$196

Porter Airlines

Feb 14

YTZ11:05 amToronto Island

1h 50m

MDW11:55 amChicago Midway

Feb 16

MDW4:15 pmChicago Midway

1h 42m

YTZ6:57 pmToronto Island

$202

Air Transat flights from Toronto to Chicago Midway Airport

Our best Air Transat deals on Toronto to Chicago Midway Airport flight tickets

Air Transat

Feb 18

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Feb 25

MDW11:05 amChicago Midway

1h 42m

YTZ1:47 pmToronto Island

$198

Air Transat

Feb 19

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Feb 26

MDW11:05 amChicago Midway

1h 42m

YTZ1:47 pmToronto Island

$201

Air Transat

Feb 12

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Feb 14

MDW12:50 pmChicago Midway

1h 42m

YTZ3:32 pmToronto Island

$236

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/9

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Fri 2/27

11:05 am-1:47 pm

Nonstop1h 42m

$191

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/5

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Tue 2/10

11:05 am-1:47 pm

Nonstop1h 42m

$196

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 2/18

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Wed 2/25

11:05 am-1:47 pm

Nonstop1h 42m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 2/18

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Wed 2/25

11:05 am-1:47 pm

Nonstop1h 42m

$200

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/19

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Thu 2/26

11:05 am-1:47 pm

Nonstop1h 42m

$201

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/14

11:05 am-11:55 am

Nonstop1h 50m

Chicago Midway

Mon 2/16

4:15 pm-6:57 pm

Nonstop1h 42m

$202

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/21

11:05 am-11:55 am

Nonstop1h 50m

Chicago Midway

Sun 2/22

4:15 pm-6:57 pm

Nonstop1h 42m

$203

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 2/9

7:45 am-12:46 pm

1 stop6h 01m

Chicago Midway

Thu 2/12

9:50 am-3:59 pm

1 stop5h 09m

$224

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/19

6:15 am-12:46 pm

1 stop7h 31m

Chicago Midway

Thu 2/26

1:28 pm-10:40 pm

1 stop8h 12m

$225

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 3/24

10:05 am-12:29 pm

1 stop3h 24m

Chicago Midway

Fri 3/27

9:30 am-11:06 pm

1 stop12h 36m

$279

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 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

Other information

What is the typical price of a round-trip flight between Toronto and Chicago Midway Airport?

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

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto, with most prices found around $172. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Toronto during the month January is also very affordable. Most momondo users find prices during this month for around $192.

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. The lowest ticket price found for a Wednesday departure recently was $217. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $292.

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

Flying to Chicago Midway Airport from Toronto in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $231 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $320. 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 Midway flight route?

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

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

There are 3 cabin classes available to choose from on Toronto to Chicago Midway 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 Midway Airport flights?

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

How have Toronto to Chicago Midway Airport flight prices changed over time?

When to book flights from Toronto to Chicago Midway Airport

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

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

Best Price Found	$215
Fastest flight time	1h 50m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is $215. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $168.

The fastest flight from Toronto to Chicago Midway Airport takes 1h 50m

Direct flights go from Toronto to Chicago Midway Airport every day.

Search flight deals

How far is Toronto to Chicago Midway by plane?
There are 443.1 mi between Toronto and Chicago Midway. Typically, this will take 1h 50m by plane in normal conditions.
When did momondo last update prices for flights from Toronto to Chicago Midway Airport?
Prices for flights from Toronto to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Toronto to Chicago Midway Airport?
As of January 2026, there is 1 operator available to choose from for flights from Toronto to Chicago Midway Airport.
How old do you have to be to fly from Toronto 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 to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Toronto to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto to Chicago Midway Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q (31.82% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (15.67%), Embraer 170 (15.47%), and Boeing 737-800 (10.05%).
What is the most popular airline from Toronto to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto and Chicago Midway Airport, the leading airline is Porter Airlines, making up 100% of the total bookings.

Best airlines flying from Toronto to Chicago Midway Airport

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

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom $80	Free Cancellation	Rating 7.9 412 reviews		Search Porter Airlines flights

Porter Airlines Flights From Toronto to Chicago Midway Airport
Porter Airlines is one of the most popular airlines flying from Toronto to Chicago Midway Airport, operating 3 flights/week on average for this route. A good Porter Airlines flight deal for Toronto to Chicago Midway Airport starts from $80 round-trip, up to an average price of $189. Our users have rated Porter Airlines at 7.9/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

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?

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?

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?

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 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.

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Cheap flights from Toronto to Chicago from $124

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 2/9. 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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Filter for what you want

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Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets

Air Transat flights from Toronto to Chicago Midway Airport

Our best Air Transat deals on Toronto to Chicago Midway Airport flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

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

What is the typical price of a round-trip flight between Toronto and 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 Toronto to Chicago Midway flight route?

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

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

There are 3 cabin classes available to choose from on Toronto to Chicago Midway 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 Midway Airport flights?

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

How have Toronto to Chicago Midway Airport flight prices changed over time?

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

Porter Airlines, Air Transat, and Delta are the most popular carriers operating from Toronto to Chicago Midway

How often are flights from Toronto to Chicago delayed?

Historically, on average around 15% 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 108 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?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday 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, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

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

As of January 2026, there are 6 flights per week flying from Toronto to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 33% of flights taking off on this day.

How long does it take to fly to Chicago Midway Airport?

When to book flights from Toronto to Chicago Midway Airport

Cheap Toronto to Chicago Midway Airport (YTO to MDW) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

How far is Toronto to Chicago Midway by plane?

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

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

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

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

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

What is the most popular airline from Toronto to Chicago Midway Airport?

Best airlines flying from Toronto to Chicago Midway Airport

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

Porter Airlines Flights From Toronto 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