How often are flights from Chicago to Toronto delayed?

Historically, on average around 15% 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 evening tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

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

The number of flights available between Chicago Midway Airport and Toronto is 3 per day as of July 2026. The most frequent departure time is 10:00AM, with 53% of daily flights leaving at noon.

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

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

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

26 flights are operational weekly from Chicago Midway Airport to Toronto as of July 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

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

Saturday 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, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 15% of their flights experiencing any sort of delay.

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

Prices for flights from Chicago Midway Airport to Toronto are refreshed on a daily basis.

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

There are 2 operators available for flights from Chicago Midway Airport to Toronto as of July 2026.

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

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.

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

The travel and health documents you'll need for your trip to Toronto 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$85 Cheap Flights from Chicago Midway Airport to Toronto in 2026

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

Prices are currently low for flights on this route. Typical prices usually range from $244 to $332. The lowest price recently found on this route was $238.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Toronto

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:20 am - 1:00 pm

MDW

YTZ

1h 40mnonstop

8:55 am - 9:45 am

YTZ

MDW

1h 50mnonstop

$238Porter Airlines

Sun, Aug 9 - Mon, Aug 17

10:25 am - 1:05 pm

MDW

YTZ

1h 40mnonstop

8:50 am - 9:40 am

YTZ

MDW

1h 50mnonstop

$239Porter Airlines

Thu, Aug 13 - Sun, Aug 16

10:25 am - 1:05 pm

MDW

YTZ

1h 40mnonstop

1:45 pm - 2:35 pm

YTZ

MDW

1h 50mnonstop

$240Porter Airlines

Fri, Aug 7 - Wed, Aug 12

3:15 pm - 5:55 pm

MDW

YTZ

1h 40mnonstop

8:50 am - 9:40 am

YTZ

MDW

1h 50mnonstop

$241Porter Airlines

Tue, Aug 18 - Sun, Aug 23

10:25 am - 1:05 pm

MDW

YTZ

1h 40mnonstop

1:45 pm - 2:35 pm

YTZ

MDW

1h 50mnonstop

$242Porter Airlines

Fri, Aug 14 - Fri, Aug 21

3:15 pm - 5:55 pm

MDW

YTZ

1h 40mnonstop

8:55 am - 9:45 am

YTZ

MDW

1h 50mnonstop

$243Porter Airlines

Tue, Aug 11 - Thu, Aug 20

9:29 am - 5:20 pm

MDW

YYZ

6h 51m

1 stop

6:00 am - 9:07 am

YYZ

MDW

4h 07m

1 stop

$279Delta

Tue, Sep 22 - Fri, Sep 25

1:28 pm - 11:01 pm

MDW

YYZ

8h 33m

1 stop

6:00 am - 12:48 pm

YYZ

MDW

7h 48m

1 stop

$290Delta

Fri, Oct 9 - Mon, Oct 12

9:29 am - 5:20 pm

MDW

YYZ

6h 51m

1 stop

12:08 pm - 6:33 pm

YYZ

MDW

7h 25m

1 stop

$298Delta

Thu, Oct 1 - Sun, Oct 4

9:29 am - 5:20 pm

MDW

YYZ

6h 51m

1 stop

12:10 pm - 6:05 pm

YYZ

MDW

6h 55m

1 stop

$299KLM

Fri, Oct 23 - Sun, Oct 25

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Delta flights from Chicago Midway Airport to Toronto

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

Delta

Sep 3

MDW9:24 amChicago Midway

7h 00m

1 stop

YYZ5:24 pmToronto Pearson Intl

Sep 6

YYZ12:09 pmToronto Pearson Intl

5h 50m

1 stop

MDW4:59 pmChicago Midway

$279

Delta

Oct 9

MDW1:28 pmChicago Midway

8h 33m

1 stop

YYZ11:01 pmToronto Pearson Intl

Oct 12

YYZ6:00 amToronto Pearson Intl

7h 48m

1 stop

MDW12:48 pmChicago Midway

$290

Delta

Oct 1

MDW9:29 amChicago Midway

6h 51m

1 stop

YYZ5:20 pmToronto Pearson Intl

Oct 4

YYZ12:08 pmToronto Pearson Intl

7h 25m

1 stop

MDW6:33 pmChicago Midway

$298

Porter Airlines flights from Chicago Midway Airport to Toronto

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

Porter Airlines

Aug 9

MDW10:20 amChicago Midway

1h 40m

YTZ1:00 pmToronto Island

Aug 17

YTZ8:55 amToronto Island

1h 50m

MDW9:45 amChicago Midway

$238

Porter Airlines

Aug 13

MDW10:25 amChicago Midway

1h 40m

YTZ1:05 pmToronto Island

Aug 16

YTZ8:50 amToronto Island

1h 50m

MDW9:40 amChicago Midway

$239

Porter Airlines

Aug 7

MDW10:25 amChicago Midway

1h 40m

YTZ1:05 pmToronto Island

Aug 12

YTZ1:45 pmToronto Island

1h 50m

MDW2:35 pmChicago Midway

$240

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 8/9

10:20 am-1:00 pm

Nonstop1h 40m

Toronto Island

Mon 8/17

8:55 am-9:45 am

Nonstop1h 50m

$238

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 8/13

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Sun 8/16

8:50 am-9:40 am

Nonstop1h 50m

$239

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/7

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Wed 8/12

1:45 pm-2:35 pm

Nonstop1h 50m

$240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 8/18

3:15 pm-5:55 pm

Nonstop1h 40m

Toronto Island

Sun 8/23

8:50 am-9:40 am

Nonstop1h 50m

$241

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/14

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Fri 8/21

1:45 pm-2:35 pm

Nonstop1h 50m

$242

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 8/11

3:15 pm-5:55 pm

Nonstop1h 40m

Toronto Island

Thu 8/20

8:55 am-9:45 am

Nonstop1h 50m

$243

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/22

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Fri 9/25

6:00 am-9:07 am

1 stop4h 07m

$279

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 10/9

1:28 pm-11:01 pm

1 stop8h 33m

Toronto Pearson Intl

Mon 10/12

6:00 am-12:48 pm

1 stop7h 48m

$290

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 10/1

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Sun 10/4

12:08 pm-6:33 pm

1 stop7h 25m

$298

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 10/23

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Sun 10/25

12:10 pm-6:05 pm

1 stop6h 55m

$299

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 Chicago Midway Airport to Toronto

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 Chicago Midway Airport and Toronto?

What is the cheapest month to fly to Toronto?

The month of January is, on average, the cheapest month to fly to Toronto from Chicago Midway Airport, with most prices found around $205. If you are unable to visit Toronto during the month of January, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $228.

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

On average, the least expensive day to fly to Toronto from Chicago Midway Airport is on a Thursday. momondo users have found tickets for Thursday departures for as low as $392. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Toronto is Sunday, with ticket prices averaging around $610.

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

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Toronto when you can find flight prices for as low as $400. Flying to Toronto in the morning is an ideal time because this is during off-peak travel hours. Flights to Toronto are more costly in the afternoon, with an average ticket price of $703. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Toronto flight route?

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

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

There are 2 cabin classes available to choose from on Chicago Midway Airport to Toronto 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 Chicago Midway Airport to Toronto flights?

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

When to book flights from Chicago Midway Airport to Toronto

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

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

Best Price Found	$165
Fastest flight time	1h 40m
Direct flights	Every day
Airports in Toronto	3 airports

The best one-way flight to Toronto from Chicago Midway Airport in the past 72 hours is $165. The best round-trip flight deal from Chicago Midway Airport to Toronto found on momondo in the last 72 hours is $237.

The fastest flight from Chicago Midway Airport to Toronto takes 1h 40m

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

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

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Toronto

How far is Chicago Midway to Toronto by plane?
Toronto is 443.1 mi away from Chicago Midway. In terms of flight time, this usually takes a little over 1h 40m.
When did momondo last update prices for flights from Chicago Midway Airport to Toronto?
Prices for flights from Chicago Midway Airport to Toronto are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Toronto?
There are 2 operators available for flights from Chicago Midway Airport to Toronto as of July 2026.
How old do you have to be to fly from Chicago Midway Airport to Toronto?
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.
What documentation or ID do you need to fly to Toronto?
The travel and health documents you'll need for your trip to Toronto 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. 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?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Toronto is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 43.37% of all bookings. The subsequent popular models are Embraer 175 at 12.26%, Embraer 175 (Enhanced Winglets) at 7.91%, and Airbus A319 at 6.08%.
What is the most popular airline from Chicago Midway Airport to Toronto?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Toronto is Porter Airlines (100% of total bookings).

Best airlines flying from Chicago Midway Airport to Toronto

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $88	Free Cancellation	Rating 7.8 8,476 reviews		Search Delta flights
Porter Airlines	PriceFrom $174	Free Cancellation	Rating 8.0 448 reviews		Search Porter Airlines flights

Porter Airlines Flights From Chicago Midway Airport to Toronto
The lowest priced Porter Airlines flight from Chicago Midway Airport to Toronto from the last 72 hours was $174. Generally, Porter Airlines has 13 flights on this route every week with an average price of $292. Porter Airlines is rated 8.0/10 by our users.

Why use momondo?

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

It is quick and easy to find Chicago to Toronto 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 Toronto that suits you.

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

Yes. All flights to Toronto from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

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 Toronto from Chicago.

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

If you are not ready to book a flight from Chicago to Toronto now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Toronto and let you know when they change.

An easier way to manage your Toronto trip

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Cheap flights from Chicago Midway Airport to Toronto from $106

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Toronto departing on 10/1. 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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Delta flights from Chicago Midway Airport to Toronto

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

Porter Airlines flights from Chicago Midway Airport to Toronto

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

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

See travel insights to Toronto from

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

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

What is the cheapest month to fly to Toronto?

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

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

What is the cheapest Chicago Midway to Toronto flight route?

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

Can stopping save me money on Chicago Midway Airport to Toronto flights?

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

How often are flights from Chicago to Toronto delayed?

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

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

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

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

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

When to book flights from Chicago Midway Airport to Toronto

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

Best Price Found

Fastest flight time

Direct flights

Airports in Toronto

Frequently asked questions about flying from Chicago Midway Airport to Toronto

Best airlines flying from Chicago Midway Airport to Toronto

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

Why use momondo?

An easier way to manage your Toronto 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 Canada

Fly into one of these airports located in Toronto

Airports listed have a maximum distance of 52.0 mi from Toronto

Fly your favorite airline to Toronto

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Toronto

List of cabin classes available on flights landing in Toronto. Availability may vary depending on flight origin and airline.

Popular cities in Canada

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

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According to popular flight searches on momondo this year

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