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

Thursday 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 16% 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.

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 16% of their flights experiencing any sort of delay.

What is the most punctual flight time for Toronto to Chicago 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 Toronto Island Airport to Chicago Midway 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 Toronto Island Airport to Chicago Midway Airport.

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

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$245 Cheap Flights from Toronto Island Airport to Chicago Midway Airport in 2026/27

Find the cheapest flights from Toronto Island Airport to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:10 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

12:28 pm - 1:34 pmMDW Chicago Midway-YTZ Toronto Island

24h 06m2 stops Atlanta Hartsfield-Jackson Newark

$485Multiple Airlines

Mon, Dec 7 - Wed, Dec 9

7:10 pm - 4:06 pmYTZ Toronto Island-MDW Chicago Midway

21h 56m2 stops Newark Atlanta Hartsfield-Jackson

5:02 pm - 11:19 amMDW Chicago Midway-YTZ Toronto Island

17h 17m2 stops Atlanta Hartsfield-Jackson Newark

$501Multiple Airlines

Thu, Dec 10 - Sun, Dec 13

4:15 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

20h 18m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson

5:02 pm - 9:39 amMDW Chicago Midway-YTZ Toronto Island

15h 37m2 stops Atlanta Hartsfield-Jackson Newark

$503Multiple Airlines

Fri, Dec 4 - Mon, Dec 7

7:10 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 pm - 11:19 amMDW Chicago Midway-YTZ Toronto Island

17h 17m2 stops Atlanta Hartsfield-Jackson Newark

$510Multiple Airlines

Fri, Dec 4 - Mon, Dec 7

7:10 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 pm - 11:19 amMDW Chicago Midway-YTZ Toronto Island

17h 17m2 stops Atlanta Hartsfield-Jackson Newark

$520Multiple Airlines

Fri, Dec 4 - Mon, Dec 7

7:10 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 pm - 9:39 amMDW Chicago Midway-YTZ Toronto Island

15h 37m2 stops Atlanta Hartsfield-Jackson Newark

$521Multiple Airlines

Fri, Dec 11 - Mon, Dec 14

4:15 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

20h 18m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson

8:37 pm - 7:55 pmMDW Chicago Midway-YTZ Toronto Island

22h 18m3 stops Orlando Atlanta Hartsfield-Jackson Washington, D.C. Dulles Intl

$528Multiple Airlines

Fri, Dec 4 - Sun, Dec 6

7:10 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 pm - 11:19 amMDW Chicago Midway-YTZ Toronto Island

17h 17m2 stops Atlanta Hartsfield-Jackson Newark

$530Multiple Airlines

Fri, Dec 4 - Mon, Dec 7

7:10 pm - 11:33 amYTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 pm - 1:34 pmMDW Chicago Midway-YTZ Toronto Island

19h 32m2 stops Atlanta Hartsfield-Jackson Newark

$541Multiple Airlines

Mon, Dec 7 - Mon, Dec 14

7:10 pm - 4:07 pmYTZ Toronto Island-MDW Chicago Midway

21h 57m2 stops Newark Atlanta Hartsfield-Jackson

12:28 pm - 9:39 amMDW Chicago Midway-YTZ Toronto Island

20h 11m2 stops Atlanta Hartsfield-Jackson Newark

$541Multiple Airlines

Wed, Dec 2 - Wed, Dec 9

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 12/7

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Wed 12/9

12:28 pm-1:34 pm

2 stops24h 06m

$485

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 12/10

7:10 pm-4:06 pm

2 stops21h 56m

Chicago Midway

Sun 12/13

5:02 pm-11:19 am

2 stops17h 17m

$501

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 12/4

4:15 pm-11:33 am

2 stops20h 18m

Chicago Midway

Mon 12/7

5:02 pm-9:39 am

2 stops15h 37m

$503

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 12/4

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Mon 12/7

5:02 pm-11:19 am

2 stops17h 17m

$510

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 12/4

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Mon 12/7

5:02 pm-11:19 am

2 stops17h 17m

$520

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 12/11

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Mon 12/14

5:02 pm-9:39 am

2 stops15h 37m

$521

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 12/4

4:15 pm-11:33 am

2 stops20h 18m

Chicago Midway

Sun 12/6

8:37 pm-7:55 pm

3 stops22h 18m

$528

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 12/4

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Mon 12/7

5:02 pm-11:19 am

2 stops17h 17m

$530

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 12/7

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Mon 12/14

5:02 pm-1:34 pm

2 stops19h 32m

$541

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 12/2

7:10 pm-4:07 pm

2 stops21h 57m

Chicago Midway

Wed 12/9

12:28 pm-9:39 am

2 stops20h 11m

$541

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 Island 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

Delays

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

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto Island Airport, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Toronto Island Airport during the month January is also very affordable. Most momondo users find prices during this month for around $204.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Toronto Island Airport. The lowest ticket price found for a Tuesday departure recently was $229. 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, Friday is the most expensive day to depart from Toronto Island Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $349.

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

Flying to Chicago Midway Airport from Toronto Island Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $274 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $290. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

There is only 1 cabin class available to choose from on Toronto Island Airport to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

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

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

Best Price Found	$245
Fastest flight time	15h 52m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Toronto Island Airport in the past 72 hours is $245. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is $485.

The fastest flight from Toronto Island Airport to Chicago Midway Airport takes 15h 52m

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

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Frequently asked questions about flying from Toronto Island Airport to Chicago Midway Airport

How far is Toronto Island to Chicago Midway by plane?
A flight from Toronto Island to Chicago Midway will travel around 442.0 mi. In terms of flight time, this usually takes a little over 15h 52m.
When did momondo last update prices for flights from Toronto Island Airport to Chicago Midway Airport?
Prices for flights from Toronto Island Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Toronto Island Airport to Chicago Midway Airport?
There is 1 operator available for flights from Toronto Island Airport to Chicago Midway Airport as of November 2026.
How old do you have to be to fly from Toronto Island Airport to Chicago Midway 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 Toronto Island Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Toronto Island Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto Island Airport and Chicago Midway Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 38.46% of the total bookings. Other popular models include Embraer 175 with 10.57%, Boeing 737-900 with 8.59%, and Embraer 175 (Enhanced Winglets) with 7.89%.
What is the most popular airline from Toronto Island Airport to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Toronto Island Airport to Chicago Midway Airport is Porter Airlines (100% of total bookings).

Best airlines flying from Toronto Island Airport to Chicago Midway Airport

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

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom $185	Free Cancellation	Rating 8.0 468 reviews		Search Porter Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Lansing

Benton Harbor

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.

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?

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 Toronto to Chicago.

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

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

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Cheap flights from Toronto Island Airport to Chicago from $245

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

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

How often are flights from Toronto to Chicago delayed?

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

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

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

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

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Toronto Island Airport to Chicago Midway Airport

Best airlines flying from Toronto Island Airport to Chicago Midway Airport

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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago Midway Airport trip

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

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