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.

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 often are flights from Toronto to Chicago delayed?

Historically, on average around 15% 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 106 minutes.

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

Porter Airlines is the most popular carrier operating from Toronto Island to Chicago Midway

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 15% of their flights experiencing any sort of delay.

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 August 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.

C$ 174 Cheap Flights from Toronto Island Airport to Chicago Midway Airport in 2026

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

2 flights are operational daily from Toronto Island Airport to Chicago Midway Airport as of August 2026. The most popular departure time for this route is 1:00p.m., with 66% of flights per day taking off in the afternoon.

Find the cheapest flights from Toronto Island Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 287Porter Airlines

Mon, 31 Aug - Wed, 2 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

11:45 a.m. - 2:25 p.m.

MDW

YTZ

1h 40mdirect

C$ 289Porter Airlines

Thu, 27 Aug - Wed, 2 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

10:25 a.m. - 1:05 p.m.

MDW

YTZ

1h 40mdirect

C$ 289Air Transat

Tue, 25 Aug - Thu, 27 Aug

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 289Porter Airlines

Fri, 28 Aug - Wed, 2 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 290Porter Airlines

Fri, 28 Aug - Tue, 1 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 290Porter Airlines

Fri, 28 Aug - Wed, 2 Sep

10:10 a.m. - 11:00 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 290Porter Airlines

Mon, 7 Sep - Thu, 10 Sep

8:50 a.m. - 9:40 a.m.

YTZ

MDW

1h 50mdirect

11:45 a.m. - 2:25 p.m.

MDW

YTZ

1h 40mdirect

C$ 291Porter Airlines

Sat, 29 Aug - Tue, 8 Sep

1:45 p.m. - 2:35 p.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 293Porter Airlines

Fri, 28 Aug - Thu, 3 Sep

8:55 a.m. - 9:45 a.m.

YTZ

MDW

1h 50mdirect

10:20 a.m. - 1:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 297Multiple Airlines

Thu, 20 Aug - Sun, 23 Aug

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Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport

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

Porter Airlines

31 Aug

YTZ8:55 a.m.Toronto Island

1h 50m

MDW9:45 a.m.Chicago Midway

2 Sep

MDW3:20 p.m.Chicago Midway

1h 40m

YTZ6:00 p.m.Toronto Island

C$ 287

Porter Airlines

28 Aug

YTZ8:55 a.m.Toronto Island

1h 50m

MDW9:45 a.m.Chicago Midway

2 Sep

MDW3:20 p.m.Chicago Midway

1h 40m

YTZ6:00 p.m.Toronto Island

C$ 290

Porter Airlines

29 Aug

YTZ8:50 a.m.Toronto Island

1h 50m

MDW9:40 a.m.Chicago Midway

8 Sep

MDW11:45 a.m.Chicago Midway

1h 40m

YTZ2:25 p.m.Toronto Island

C$ 291

Air Transat flights from Toronto Island Airport to Chicago Midway Airport

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

Air Transat

25 Aug

YTZ8:55 a.m.Toronto Island

1h 50m

MDW9:45 a.m.Chicago Midway

27 Aug

MDW10:25 a.m.Chicago Midway

1h 40m

YTZ1:05 p.m.Toronto Island

C$ 289

Air Transat

19 Aug

YTZ1:45 p.m.Toronto Island

1h 50m

MDW2:35 p.m.Chicago Midway

26 Aug

MDW3:15 p.m.Chicago Midway

1h 40m

YTZ5:55 p.m.Toronto Island

C$ 329

momondo Fare Finder

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 - MDW

YTZMDW

Toronto Island

Mon 31/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 287

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 27/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 1/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 2/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 7/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Thu 10/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 29/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Tue 8/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 291

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Thu 3/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 23/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 297

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

Airlines

Delays

Other information

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

Prices are currently low for flights on this route.

Typical prices usually range from C$ 289 to C$ 579.
The lowest price recently found on this route was C$ 287.

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$ 286.

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 Wednesday when prices can be found for as low as C$ 317. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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$ 360.

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$ 330. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 679.

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$ 181
Fastest flight time	1h 50m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Toronto Island Airport in the past 72 hours is C$ 181. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 287.

The fastest flight from Toronto Island Airport to Chicago Midway Airport takes 1h 50m

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

Search flight deals

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 1h 50m.
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 August 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 36.18% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 10.48%, Boeing 737-800 at 9.95%, and Boeing 737-900 at 8.41%.
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$ 200	Free Cancellation	Rating 8.0 449 reviews		Search Porter Airlines flights

Porter Airlines Flights From Toronto Island Airport to Chicago Midway Airport
Porter Airlines flies from Toronto Island Airport to Chicago Midway Airport around 9 times per week, with 449 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Toronto Island Airport to Chicago Midway Airport in the last 72 hours was C$ 200 (round-trip), much lower than the average airfare cost of C$ 331 for Porter Airlines flights on this route.

Merrillville

Hammond

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.

An easier way to manage your Chicago Midway Airport trip

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Cheap flights from Toronto Island Airport to Chicago from C$ 191

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 28/8. 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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Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport

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

Air Transat flights from Toronto Island Airport to Chicago Midway Airport

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

momondo Fare Finder

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

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?

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

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?

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

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

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

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According to popular flight searches on momondo this year

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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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