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

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

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 Tue, with 33% of flights taking off on this day.

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?

Wednesday 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.

How often are flights from Toronto to Chicago delayed?

Historically, on average around 14% 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 107 minutes.

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 46m.

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

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Toronto to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:00 am - 11:50 am

YTZ

MDW

1h 50mnonstop

12:45 pm - 3:27 pm

MDW

YTZ

1h 42mnonstop

$184Porter Airlines

Sat, Feb 21 - Sat, Feb 28

11:00 am - 11:50 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$185Porter Airlines

Sat, Jan 31 - Mon, Feb 2

2:30 pm - 3:20 pm

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$186Multiple Airlines

Sun, Feb 8 - Tue, Feb 10

11:00 am - 11:50 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$187Porter Airlines

Sat, Feb 7 - Sun, Feb 8

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

4:15 pm - 6:57 pm

MDW

YTZ

1h 42mnonstop

$188Porter Airlines

Fri, Mar 13 - Sun, Mar 15

11:05 am - 11:55 am

YTZ

MDW

1h 50mnonstop

12:50 pm - 3:32 pm

MDW

YTZ

1h 42mnonstop

$189Porter Airlines

Sat, Feb 21 - Sat, Feb 28

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

4:15 pm - 6:57 pm

MDW

YTZ

1h 42mnonstop

$190Porter Airlines

Thu, Mar 12 - Sun, Mar 15

10:05 am - 12:46 pm

YYZ

MDW

3h 41m1 stop

9:33 am - 4:12 pm

MDW

YYZ

5h 39m1 stop

$215Delta

Thu, Feb 5 - Sat, Feb 7

7:45 am - 12:46 pm

YYZ

MDW

6h 01m1 stop

9:33 am - 4:12 pm

MDW

YYZ

5h 39m1 stop

$216Delta

Thu, Feb 5 - Sun, Feb 8

7:45 am - 12:46 pm

YYZ

MDW

6h 01m1 stop

9:33 am - 4:12 pm

MDW

YYZ

5h 39m1 stop

$217Delta

Thu, Feb 5 - Sun, Feb 8

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 21

YTZ11:00 amToronto Island

1h 50m

MDW11:50 amChicago Midway

Feb 28

MDW12:45 pmChicago Midway

1h 42m

YTZ3:27 pmToronto Island

$184

Porter Airlines

Jan 31

YTZ11:00 amToronto Island

1h 50m

MDW11:50 amChicago Midway

Feb 2

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

$185

Porter Airlines

Feb 7

YTZ11:00 amToronto Island

1h 50m

MDW11:50 amChicago Midway

Feb 8

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

$187

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 13

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Feb 15

MDW4:15 pmChicago Midway

1h 42m

YTZ6:57 pmToronto Island

$218

Air Transat

Mar 27

YTZ9:15 amToronto Island

1h 50m

MDW10:05 amChicago Midway

Mar 30

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

$238

Air Transat

Jan 15

YTZ9:20 amToronto Island

1h 50m

MDW10:10 amChicago Midway

Jan 18

MDW4:15 pmChicago Midway

1h 42m

YTZ6:57 pmToronto Island

$369

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

Sat 2/21

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Sat 2/28

12:45 pm-3:27 pm

Nonstop1h 42m

$184

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 1/31

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Mon 2/2

11:00 am-1:42 pm

Nonstop1h 42m

$185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 2/8

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Tue 2/10

11:00 am-1:42 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/7

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Sun 2/8

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 3/13

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 3/15

4:15 pm-6:57 pm

Nonstop1h 42m

$188

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/21

11:05 am-11:55 am

Nonstop1h 50m

Chicago Midway

Sat 2/28

12:50 pm-3:32 pm

Nonstop1h 42m

$189

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 3/12

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 3/15

4:15 pm-6:57 pm

Nonstop1h 42m

$190

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

10:05 am-12:46 pm

1 stop3h 41m

Chicago Midway

Sat 2/7

9:33 am-4:12 pm

1 stop5h 39m

$215

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

7:45 am-12:46 pm

1 stop6h 01m

Chicago Midway

Sun 2/8

9:33 am-4:12 pm

1 stop5h 39m

$216

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

7:45 am-12:46 pm

1 stop6h 01m

Chicago Midway

Sun 2/8

9:33 am-4:12 pm

1 stop5h 39m

$217

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 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 February is also very affordable. Most momondo users find prices during this month for around $200.

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 $291.

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 $327. 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	$212
Fastest flight time	1h 49m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is $212. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $216.

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

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 49m 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 (30.67% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (15.48%), Embraer 170 (14.21%), and Boeing 737-800 (11.71%).
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 $158	Free Cancellation	Rating 8.0 406 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 $158 round-trip, up to an average price of $258. Our users have rated Porter Airlines at 8.0/10.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sat 2/7

Sat 2/14

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago

Popular cities in the United States

Flights to New York John F Kennedy Intl Airportfrom $58

Flights to Newark Airportfrom $49

Flights to New York LaGuardia Airportfrom $49

Flights to Dallas/Fort Worth Airportfrom $57

Flights to Chicago O'Hare Intl Airportfrom $58

Flights to Washington, D.C. Dulles Intl Airportfrom $58

Flights to Washington, D.C. Reagan-National Airportfrom $61

Flights to Orlando Airportfrom $49

Flights to Dallas Love Field Airport

Cheap flights from Toronto to Chicago from $116

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 3/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

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 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 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 14% 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 107 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?

Wednesday 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 Tue, 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