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Cheap flights from Toronto Island Airport to Chicago Midway Airport from $134

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 Midway Airport departing on 2/13. 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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Find the cheapest flights from Toronto Island Airport to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Toronto Island Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto Island Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from Toronto Island Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Toronto Island Airport to Chicago

Find recent round-trip train or bus tickets from Toronto Island Airport to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Feb 14 - Mon, Feb 17
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$231Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$233Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$242Porter Airlines
Find Deal
Fri, Jan 17 - Thu, Feb 13
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$250Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$251Porter Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 20
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$279Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$303Air Transat
Find Deal
Thu, Jan 16 - Sun, Jan 19
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:40 am - 4:48 pmMDW-YTZ
10h 08m2 stops
Mon, Jan 6 - Fri, Jan 10
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$436Air Transat
Find Deal
Wed, Jan 1 - Wed, Jan 1
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$134Porter Airlines
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Thu, Feb 13
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$145Porter Airlines
Find Deal
Wed, Jan 15
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$148Porter Airlines
Find Deal
Wed, Jan 22
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$149Porter Airlines
Find Deal
Sun, Jan 12
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
$151Porter Airlines
Find Deal
Mon, Jan 6
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$153Porter Airlines
Find Deal
Sat, Jan 25
11:20 am - 5:33 pmYTZ-MDW
7h 13m1 stop
Fri, Feb 28
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$208Air Transat
Find Deal
Sat, Mar 29
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$274Air Transat
Find Deal
Fri, Jun 6
10:45 am - 11:35 amYTZ-MDW
1h 50mnonstop
$286Air Transat
Find Deal
Sat, Jun 7
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$356Porter Airlines
Find Deal
Wed, Dec 25 - Sat, Jan 25
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$357Porter Airlines
Find Deal
Thu, Dec 26 - Wed, Jan 29
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$365Porter Airlines
Find Deal
Thu, Dec 26 - Sat, Jan 4
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$366Porter Airlines
Find Deal
Mon, Dec 23 - Mon, Jan 6
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$375Porter Airlines
Find Deal
Fri, Dec 27 - Mon, Dec 30
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$383Porter Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 4
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$483Air Transat
Find Deal
Fri, Dec 27 - Fri, Jan 3
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
6:00 am - 4:58 pmMDW-YTZ
9h 58m2 stops
Fri, Dec 27 - Mon, Dec 30
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$527Air Transat
Find Deal
Mon, Dec 23 - Mon, Dec 30
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$531Air Transat
Find Deal
Thu, Dec 26 - Sun, Jan 5
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Feb 14 - Mon, Feb 17
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$231Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$233Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$242Porter Airlines
Find Deal
Fri, Jan 17 - Thu, Feb 13
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$250Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$251Porter Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 20
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$279Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$303Air Transat
Find Deal
Thu, Jan 16 - Sun, Jan 19
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$436Air Transat
Find Deal
Wed, Jan 1 - Wed, Jan 1
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
Sun, Jan 5 - Sun, Jan 5

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
Feb 14
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 17
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island
Porter Airlines
Feb 13
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 16
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island
Porter Airlines
Feb 13
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 16
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island

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
Feb 13
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 16
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island
Air Transat
Jan 16
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Jan 19
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island
Air Transat
Dec 28
YTZ9:40 amToronto Island
1h 50m
MDW10:30 amChicago Midway
Jan 4
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island

See travel insights to Chicago from

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

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?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto Island Airport, with most prices found around $219. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Toronto Island Airport during the month July is also very affordable. Most momondo users find prices during this month for around $233.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Toronto Island Airport. The lowest ticket price found for a Wednesday departure recently was $228. 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, Sunday 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 $385.

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 in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $253 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $284. 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

How far in advance should I book a flight to Chicago Midway Airport?

We recommend purchasing flights from Toronto Island Airport to Chicago Midway Airport 58 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $268. In the past 72 hours, momondo users found flights from Toronto Island Airport to Chicago Midway Airport for as low as $196.

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

There are 3 cabin classes available to choose from on Toronto Island to Chicago Midway 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 Toronto Island Airport to Chicago Midway Airport flights?

You could potentially save up to 45% on your flight if you consider stops on a Toronto Island Airport to Chicago Midway Airport flight.

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

As of December 2024, prices for Toronto Island Airport to Chicago Midway Airport flights are approximately 47% more expensive when compared to flights at the same time last year.

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

$134

Fastest flight time

1h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto Island Airport in the past 72 hours is $134. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is $230.
The fastest flight from Toronto Island Airport to Chicago Midway Airport takes 1h 45m
Direct flights go from Toronto Island Airport to Chicago Midway Airport every day.

  • 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 1h 45m.

  • 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?

  • 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?

  • What is the most popular airline 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
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $206Free CancellationRating
7.9
283 reviews
Search Porter Airlines flights
  • Porter Airlines Flights From Toronto Island Airport to Chicago Midway Airport

    Across 10 Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport this week, the average price was $257, with the best Porter Airlines deals starting from $206 round-trip. 283 users have rated Porter Airlines on momondo, with an average score of 7.9/10.


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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