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.

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

Thursday is statistically the day of the week that experiences the fewest 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 has had the least 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 departing 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 for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Toronto Island Airport to Chicago Midway Airport.

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

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

C$ 292 Cheap Flights from Toronto Island Airport to Chicago Midway Airport in 2026/27

Find the cheapest flights from Toronto Island Airport to Chicago

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One-way

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7:10 p.m. - 11:33 a.m.YTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 p.m. - 9:39 a.m.MDW Chicago Midway-YTZ Toronto Island

15h 37m2 stops Atlanta Hartsfield-Jackson Newark

C$ 610Multiple Airlines

Tue, 1 Dec - Thu, 3 Dec

7:10 p.m. - 11:33 a.m.YTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

12:28 p.m. - 9:39 a.m.MDW Chicago Midway-YTZ Toronto Island

20h 11m2 stops Atlanta Hartsfield-Jackson Newark

C$ 640Multiple Airlines

Tue, 1 Dec - Sat, 5 Dec

7:10 p.m. - 7:33 a.m.YTZ Toronto Island-MDW Chicago Midway

13h 23m2 stops Newark Atlanta Hartsfield-Jackson

1:16 p.m. - 12:50 p.m.MDW Chicago Midway-YTZ Toronto Island

22h 34m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington

C$ 651Multiple Airlines

Fri, 20 Nov - Mon, 23 Nov

4:30 p.m. - 8:14 a.m.YTZ Toronto Island-MDW Chicago Midway

16h 44m2 stops Newark Atlanta Hartsfield-Jackson

1:16 p.m. - 9:39 a.m.MDW Chicago Midway-YTZ Toronto Island

19h 23m2 stops Atlanta Hartsfield-Jackson Newark

C$ 670Multiple Airlines

Sat, 21 Nov - Sun, 22 Nov

7:10 p.m. - 1:45 p.m.YTZ Toronto Island-MDW Chicago Midway

19h 35m2 stops Newark Atlanta Hartsfield-Jackson

1:16 p.m. - 11:19 a.m.MDW Chicago Midway-YTZ Toronto Island

21h 03m2 stops Atlanta Hartsfield-Jackson Newark

C$ 677Multiple Airlines

Fri, 20 Nov - Sun, 22 Nov

7:10 p.m. - 11:33 a.m.YTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 p.m. - 11:19 a.m.MDW Chicago Midway-YTZ Toronto Island

17h 17m2 stops Atlanta Hartsfield-Jackson Newark

C$ 680Multiple Airlines

Fri, 11 Dec - Mon, 14 Dec

7:10 p.m. - 11:55 a.m.YTZ Toronto Island-MDW Chicago Midway

17h 45m2 stops Newark Atlanta Hartsfield-Jackson

1:16 p.m. - 11:19 a.m.MDW Chicago Midway-YTZ Toronto Island

21h 03m2 stops Atlanta Hartsfield-Jackson Newark

C$ 687Multiple Airlines

Thu, 19 Nov - Sun, 22 Nov

7:10 p.m. - 11:33 a.m.YTZ Toronto Island-MDW Chicago Midway

17h 23m2 stops Newark Atlanta Hartsfield-Jackson

5:02 p.m. - 1:34 p.m.MDW Chicago Midway-YTZ Toronto Island

19h 32m2 stops Atlanta Hartsfield-Jackson Newark

C$ 691Multiple Airlines

Tue, 1 Dec - Fri, 4 Dec

7:00 a.m. - 11:47 p.m.YTZ Toronto Island-MDW Chicago Midway

17h 47m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

1:16 p.m. - 11:51 a.m.MDW Chicago Midway-YTZ Toronto Island

21h 35m3 stops Atlanta Hartsfield-Jackson Newark Montreal Pierre Elliott Trudeau Intl

C$ 698Multiple Airlines

Thu, 19 Nov - Sun, 22 Nov

7:10 p.m. - 4:07 p.m.YTZ Toronto Island-MDW Chicago Midway

21h 57m2 stops Newark Atlanta Hartsfield-Jackson

5:02 p.m. - 1:34 p.m.MDW Chicago Midway-YTZ Toronto Island

19h 32m2 stops Atlanta Hartsfield-Jackson Newark

C$ 701Multiple Airlines

Wed, 2 Dec - Fri, 4 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

7:35 a.m. - 5:47 p.m.YTZ Toronto Island-MDW Chicago Midway

11h 12m2 stops Newark Atlanta Hartsfield-Jackson

12:28 p.m. - 9:39 a.m.MDW Chicago Midway-YTZ Toronto Island

20h 11m2 stops Atlanta Hartsfield-Jackson Newark

C$ 923Multiple Airlines

Tue, 3 Nov - Wed, 2 Dec

7:35 a.m. - 5:47 p.m.YTZ Toronto Island-MDW Chicago Midway

11h 12m2 stops Newark Atlanta Hartsfield-Jackson

12:33 p.m. - 9:39 a.m.MDW Chicago Midway-YTZ Toronto Island

20h 06m2 stops Atlanta Hartsfield-Jackson Newark

C$ 1,010Multiple Airlines

Tue, 3 Nov - Tue, 1 Dec

7:35 a.m. - 5:47 p.m.YTZ Toronto Island-MDW Chicago Midway

11h 12m2 stops Newark Atlanta Hartsfield-Jackson

6:42 p.m. - 9:58 p.m.MDW Chicago Midway-YTZ Toronto Island

26h 16m3 stops Atlanta Hartsfield-Jackson Fort Lauderdale Ottawa

C$ 1,155Multiple Airlines

Wed, 4 Nov - Thu, 5 Nov

7:10 p.m. - 5:47 p.m.YTZ Toronto Island-MDW Chicago Midway

23h 37m3 stops Ottawa Orlando Atlanta Hartsfield-Jackson

6:42 p.m. - 9:58 p.m.MDW Chicago Midway-YTZ Toronto Island

26h 16m3 stops Atlanta Hartsfield-Jackson Orlando Ottawa

C$ 1,544Multiple Airlines

Wed, 4 Nov - Sat, 7 Nov

7:00 a.m. - 11:47 p.m.YTZ Toronto Island-MDW Chicago Midway

17h 47m3 stops Ottawa Newark Atlanta Hartsfield-Jackson

6:44 p.m. - 9:45 a.m.MDW Chicago Midway-YTZ Toronto Island

14h 01m2 stops Detroit Metropolitan Wayne County Montreal Pierre Elliott Trudeau Intl

C$ 1,933Multiple Airlines

Tue, 3 Nov - Wed, 4 Nov

7:35 a.m. - 11:47 p.m.YTZ Toronto Island-MDW Chicago Midway

17h 12m2 stops Newark Atlanta Hartsfield-Jackson

6:44 p.m. - 9:45 a.m.MDW Chicago Midway-YTZ Toronto Island

14h 01m2 stops Detroit Metropolitan Wayne County Montreal Pierre Elliott Trudeau Intl

C$ 2,181Multiple Airlines

Tue, 3 Nov - Wed, 4 Nov

7:35 a.m. - 5:47 p.m.YTZ Toronto Island-MDW Chicago Midway

11h 12m2 stops Newark Atlanta Hartsfield-Jackson

9:29 a.m. - 9:19 p.m.MDW Chicago Midway-YTZ Toronto Island

10h 50m2 stops Detroit Metropolitan Wayne County Montreal Pierre Elliott Trudeau Intl

C$ 2,236Multiple Airlines

Wed, 4 Nov - Thu, 5 Nov

5:50 p.m. - 9:32 a.m.YTZ Toronto Island-MDW Chicago Midway

16h 42m2 stops Montreal Pierre Elliott Trudeau Intl Detroit Metropolitan Wayne County

12:27 p.m. - 11:09 a.m.MDW Chicago Midway-YTZ Toronto Island

21h 42m2 stops Minneapolis St Paul Montreal Pierre Elliott Trudeau Intl

C$ 2,804Multiple Airlines

Tue, 3 Nov - Fri, 6 Nov

5:50 p.m. - 9:32 a.m.YTZ Toronto Island-MDW Chicago Midway

16h 42m2 stops Montreal Pierre Elliott Trudeau Intl Detroit Metropolitan Wayne County

6:44 p.m. - 11:09 a.m.MDW Chicago Midway-YTZ Toronto Island

15h 25m2 stops Detroit Metropolitan Wayne County Montreal Pierre Elliott Trudeau Intl

C$ 2,838Multiple Airlines

Wed, 4 Nov - Fri, 6 Nov

5:15 p.m. - 4:47 p.m.YTZ Toronto Island-MDW Chicago Midway

24h 32m3 stops Ottawa Edmonton Minneapolis St Paul

5:31 p.m. - 11:09 a.m.MDW Chicago Midway-YTZ Toronto Island

16h 38m2 stops Minneapolis St Paul Montreal Pierre Elliott Trudeau Intl

C$ 5,054Multiple Airlines

Sun, 1 Nov - Wed, 4 Nov

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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

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 1/12

7:10 p.m.-11:33 a.m.

2 stops17h 23m

Chicago Midway

Thu 3/12

5:02 p.m.-9:39 a.m.

2 stops15h 37m

C$ 610

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 1/12

7:10 p.m.-11:33 a.m.

2 stops17h 23m

Chicago Midway

Sat 5/12

12:28 p.m.-9:39 a.m.

2 stops20h 11m

C$ 640

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 20/11

7:10 p.m.-7:33 a.m.

2 stops13h 23m

Chicago Midway

Mon 23/11

1:16 p.m.-12:50 p.m.

2 stops22h 34m

C$ 651

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 21/11

4:30 p.m.-8:14 a.m.

2 stops16h 44m

Chicago Midway

Sun 22/11

1:16 p.m.-9:39 a.m.

2 stops19h 23m

C$ 670

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 20/11

7:10 p.m.-1:45 p.m.

2 stops19h 35m

Chicago Midway

Sun 22/11

1:16 p.m.-11:19 a.m.

2 stops21h 03m

C$ 677

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 11/12

7:10 p.m.-11:33 a.m.

2 stops17h 23m

Chicago Midway

Mon 14/12

5:02 p.m.-11:19 a.m.

2 stops17h 17m

C$ 680

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 19/11

7:10 p.m.-11:55 a.m.

2 stops17h 45m

Chicago Midway

Sun 22/11

1:16 p.m.-11:19 a.m.

2 stops21h 03m

C$ 687

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 1/12

7:10 p.m.-11:33 a.m.

2 stops17h 23m

Chicago Midway

Fri 4/12

5:02 p.m.-1:34 p.m.

2 stops19h 32m

C$ 691

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 19/11

7:00 a.m.-11:47 p.m.

2 stops17h 47m

Chicago Midway

Sun 22/11

1:16 p.m.-11:51 a.m.

3 stops21h 35m

C$ 698

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 2/12

7:10 p.m.-4:07 p.m.

2 stops21h 57m

Chicago Midway

Fri 4/12

5:02 p.m.-1:34 p.m.

2 stops19h 32m

C$ 701

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 typical price of a round-trip flight between Toronto Island Airport and Chicago Midway Airport?

Prices are currently high for flights on this route.

Typical prices usually range from C$ 335 to C$ 605.
The lowest price recently found on this route was C$ 610.

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

In general, February is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 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 C$ 285.

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

The cheapest day to depart on your flight to Chicago Midway Airport is on a Thursday when prices can be found for as low as C$ 321. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto Island Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 388.

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

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Toronto Island Airport to Chicago Midway Airport during this time can be as low as C$ 334. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the afternoon when prices are around C$ 442.

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	C$ 292
Fastest flight time	11h 12m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Toronto Island Airport in the past 72 hours is C$ 292. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 610.

The fastest flight from Toronto Island Airport to Chicago Midway Airport takes 11h 12m

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?
Chicago Midway is 711.3 km away from Toronto Island. In terms of flight time, this usually takes a little over 11h 12m.
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 are updated 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 October 2026.
How old do you have to be to fly from Toronto Island Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Toronto Island Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway 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 Chicago Midway 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 Toronto Island Airport to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Toronto Island Airport to Chicago Midway Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 40.74% of all bookings. The subsequent popular models are Boeing 737-900 at 9.24%, Embraer 175 (Enhanced Winglets) at 8.25%, and Boeing 737 MAX 8 at 7.15%.
What is the most popular airline from Toronto Island Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Toronto Island Airport and Chicago Midway Airport, the leading airline is Porter Airlines, making up 100% of the 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 C$ 249	Free Cancellation	Rating 8.0 467 reviews		Search Porter Airlines flights

Merrillville

Hammond

Benton Harbor

Munster

Valparaiso

Portage

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

Finding the right flight to Chicago from Toronto is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.

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

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 Chicago from Toronto.

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.

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Cheap flights from Toronto Island Airport to Chicago from C$ 292

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 Island Airport to Chicago departing on 1/12. 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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See travel insights to Chicago from

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

What is the typical price of a round-trip flight between Toronto Island Airport 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 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

Travelling to a place near Chicago?

Why use momondo?

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

Toronto Island Airport flight routes

According to popular flight searches on momondo this year

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Fly your favourite airline to Chicago

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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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