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

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

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

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

How often are flights from Chicago to Toronto delayed?

Historically, on average around 12% of flights between Chicago and Toronto have experienced a delay on any given week. The average delay length over the past 12 months has been 116 minutes.

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.

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

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

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

What documentation or ID do you need to fly to Toronto Island Airport?

The travel and health documents you'll need for your trip to Toronto Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Toronto Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$83 Cheap Flights from Chicago Midway Airport to Toronto Island Airport in 2025/26

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

12 flights are operational weekly from Chicago Midway Airport to Toronto Island Airport as of October 2025. The most popular departure day for this route is Wed, with 33% of flights per week taking off on this day.

Q: How many flights depart from Chicago Midway Airport to Toronto Island Airport on average per day?

The number of flights available between Chicago Midway Airport and Toronto Island Airport is 1 per day as of October 2025. The most frequent departure time is 11:00AM, with 53% of daily flights leaving at noon.

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Find the cheapest flights from Chicago Midway Airport to Toronto

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11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

11:00 am - 11:50 amYTZ-MDW

1h 50mnonstop

$188Porter Airlines

Find Deal

Wed, Nov 19 - Sat, Nov 22

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$190Porter Airlines

Find Deal

Wed, Nov 12 - Sun, Nov 16

4:15 pm - 6:57 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$191Porter Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$192Porter Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

2:30 pm - 3:20 pmYTZ-MDW

1h 50mnonstop

$193Porter Airlines

Find Deal

Wed, Nov 12 - Thu, Nov 13

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$194Porter Airlines

Find Deal

Thu, Nov 13 - Sun, Nov 16

4:15 pm - 6:57 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$195Porter Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

2:30 pm - 3:20 pmYTZ-MDW

1h 50mnonstop

$196Porter Airlines

Find Deal

Thu, Nov 13 - Fri, Nov 14

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

2:30 pm - 3:20 pmYTZ-MDW

1h 50mnonstop

$219Multiple Airlines

Find Deal

Tue, Nov 11 - Fri, Nov 14

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

2:30 pm - 3:20 pmYTZ-MDW

1h 50mnonstop

$244Air Transat

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Mon, Dec 8 - Thu, Dec 11

Air Transat flights from Chicago Midway Airport to Toronto Island Airport

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

Air Transat

Dec 8

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

Dec 11

YTZ2:30 pmToronto Island

1h 50m

MDW3:20 pmChicago Midway

$244

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Air Transat

Nov 12

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

Nov 22

YTZ11:00 amToronto Island

1h 50m

MDW11:50 amChicago Midway

$267

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Porter Airlines flights from Chicago Midway Airport to Toronto Island Airport

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

Porter Airlines

Nov 19

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

Nov 22

YTZ11:00 amToronto Island

1h 50m

MDW11:50 amChicago Midway

$188

Find similar

Porter Airlines

Nov 12

MDW11:00 amChicago Midway

1h 42m

YTZ1:42 pmToronto Island

Nov 16

YTZ9:15 amToronto Island

1h 50m

MDW10:05 amChicago Midway

$190

Find similar

Porter Airlines

Dec 5

MDW4:15 pmChicago Midway

1h 42m

YTZ6:57 pmToronto Island

Dec 7

YTZ9:15 amToronto Island

1h 50m

MDW10:05 amChicago Midway

$191

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momondo Fare Finder

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

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Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/19

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

$188

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/12

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$190

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 12/8

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 12/11

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/12

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 11/13

2:30 pm-3:20 pm

Nonstop1h 50m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/13

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$194

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/13

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 11/14

2:30 pm-3:20 pm

Nonstop1h 50m

$196

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 11/11

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 11/14

2:30 pm-3:20 pm

Nonstop1h 50m

$219

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 12/8

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 12/11

2:30 pm-3:20 pm

Nonstop1h 50m

$244

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

If you aren’t able to travel during the month of July, then book flights to Toronto Island Airport from Chicago Midway Airport during June instead. Flights to Toronto Island Airport in June, while not as cheap as those in July, still average around $192.

What is the cheapest day to depart on your flight to Toronto Island Airport?

The cheapest day to depart on your flight to Toronto Island Airport is on a Saturday when prices can be found for as low as $256. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $334. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.

What is the cheapest time of day to depart on your flight to Toronto Island Airport?

Our data shows that the cheapest Chicago Midway Airport to Toronto Island Airport flights are usually those with departure times in the afternoon. Our users have found flights to Toronto Island Airport in the afternoon for as low as $268. In contrast, the most expensive time of day to depart to Toronto Island Airport is in the evening when prices are around $311.

What is the cheapest Chicago Midway to Toronto Island flight route?

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

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

There are 3 cabin classes available to choose from on Chicago Midway to Toronto Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of October 2025, prices for Chicago Midway Airport to Toronto Island Airport flights are approximately 40% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Toronto Island Airport

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

Estimated round-trip price

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

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

Best Price Found	$186
Fastest flight time	1h 42m
Direct flights	Every day

The best one-way flight to Toronto Island Airport from Chicago Midway Airport in the past 72 hours is $186. The best round-trip flight deal from Chicago Midway Airport to Toronto Island Airport found on momondo in the last 72 hours is $257.

The fastest flight from Chicago Midway Airport to Toronto Island Airport takes 1h 42m

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

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How far is Chicago Midway to Toronto Island by plane?
The straight-line distance from Chicago Midway to Toronto Island is 442.0 mi. In terms of flight time, this usually takes a little over 1h 42m.
When did momondo last update prices for flights from Chicago Midway Airport to Toronto Island Airport?
Prices for flights from Chicago Midway Airport to Toronto Island Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Toronto Island Airport?
There is 1 operator available for flights from Chicago Midway Airport to Toronto Island Airport as of October 2025.
How old do you have to be to fly from Chicago Midway Airport to Toronto Island 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 Chicago Midway Airport to Toronto Island Airport.
What documentation or ID do you need to fly to Toronto Island Airport?
The travel and health documents you'll need for your trip to Toronto Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Toronto Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Toronto Island Airport?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Toronto Island Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 27.76% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 17.41%, Embraer 175 at 12.08%, and Airbus A319 at 8.50%.
What is the most popular airline from Chicago Midway Airport to Toronto Island Airport?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Toronto Island Airport is Porter Airlines, representing 100% of all bookings.

Best airlines flying from Chicago Midway Airport to Toronto Island Airport

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

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom $185	Free Cancellation	Rating 8.0 384 reviews		Search Porter Airlines flights

Porter Airlines Flights From Chicago Midway Airport to Toronto Island Airport
Porter Airlines operates around 6 flights from Chicago Midway Airport to Toronto Island Airport every week. The average price of these flights found in the last 72 hours has been $234, but momondo users have found Porter Airlines deals from Chicago Midway Airport to Toronto Island Airport from as low as $185 round-trip. Porter Airlines has been scored 8.0/10 in 384 reviews.

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Toronto for you.

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

All flight searches from Chicago to Toronto on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Toronto.

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

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

An easier way to manage your Toronto Island Airport trip

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Cheap flights from Chicago Midway Airport to Toronto from $83

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Air Transat flights from Chicago Midway Airport to Toronto Island Airport

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

Porter Airlines flights from Chicago Midway Airport to Toronto Island Airport

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

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

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

What is the cheapest month to fly to Toronto Island Airport?

If you aren’t able to travel during the month of July, then book flights to Toronto Island Airport from Chicago Midway Airport during June instead. Flights to Toronto Island Airport in June, while not as cheap as those in July, still average around $192.

What is the cheapest day to depart on your flight to Toronto Island Airport?

What is the cheapest time of day to depart on your flight to Toronto Island Airport?

What is the cheapest Chicago Midway to Toronto Island flight route?

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

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

There are 3 cabin classes available to choose from on Chicago Midway to Toronto Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of October 2025, prices for Chicago Midway Airport to Toronto Island Airport flights are approximately 40% cheaper when compared to flights at the same time last year.

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

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

How often are flights from Chicago to Toronto delayed?

Historically, on average around 12% of flights between Chicago and Toronto have experienced a delay on any given week. The average delay length over the past 12 months has been 116 minutes.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon 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 Chicago to Toronto flights?

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

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

The number of flights available between Chicago Midway Airport and Toronto Island Airport is 1 per day as of October 2025. The most frequent departure time is 11:00AM, with 53% of daily flights leaving at noon.

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

12 flights are operational weekly from Chicago Midway Airport to Toronto Island Airport as of October 2025. The most popular departure day for this route is Wed, with 33% of flights per week taking off on this day.

When to book flights from Chicago Midway Airport to Toronto Island Airport

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

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

Best Price Found

Fastest flight time

Direct flights

How far is Chicago Midway to Toronto Island by plane?

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

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

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

What documentation or ID do you need to fly to Toronto Island Airport?

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

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

Best airlines flying from Chicago Midway Airport to Toronto Island Airport

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

Porter Airlines Flights From Chicago Midway Airport to Toronto Island Airport

Why use momondo?

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

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

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

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

An easier way to manage your Toronto Island 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 Toronto

Popular cities in Canada

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