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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 193

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 13/2. 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 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 332Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 335Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 337Porter Airlines
Find Deal
Fri, 14 Feb - Mon, 17 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 345Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 348Porter Airlines
Find Deal
Fri, 17 Jan - Thu, 13 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 357Porter Airlines
Find Deal
Mon, 20 Jan - Wed, 22 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 380Air Transat
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 383Air Transat
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 401Air Transat
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
5:30 a.m. - 4:48 p.m.MDW-YTZ
10h 18m2 stops
C$ 436
Find Deal
Fri, 17 Jan - Fri, 24 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 193Porter Airlines
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Thu, 13 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 203Porter Airlines
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Tue, 18 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 207Porter Airlines
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Wed, 15 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 209Porter Airlines
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Sat, 18 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 213Porter Airlines
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Wed, 15 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 214Porter Airlines
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Sun, 12 Jan
1:05 p.m. - 7:32 a.m.YTZ-MDW
19h 27m3 stops
C$ 253
Find Deal
Mon, 3 Mar
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 299Air Transat
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Sat, 29 Mar
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 301Air Transat
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Sat, 29 Mar
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 396Air Transat
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Tue, 29 Apr
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 514Porter Airlines
Find Deal
Thu, 26 Dec - Wed, 29 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 527Porter Airlines
Find Deal
Mon, 23 Dec - Mon, 6 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 529Porter Airlines
Find Deal
Mon, 23 Dec - Mon, 6 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 534Porter Airlines
Find Deal
Wed, 25 Dec - Sat, 4 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 560Porter Airlines
Find Deal
Thu, 26 Dec - Sat, 28 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 586Porter Airlines
Find Deal
Thu, 26 Dec - Wed, 1 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 587Porter Airlines
Find Deal
Wed, 25 Dec - Mon, 30 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 594Porter Airlines
Find Deal
Wed, 25 Dec - Sat, 28 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
6:00 a.m. - 4:58 p.m.MDW-YTZ
9h 58m2 stops
C$ 783
Find Deal
Wed, 25 Dec - Mon, 30 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
6:00 a.m. - 4:58 p.m.MDW-YTZ
9h 58m2 stops
C$ 847
Find Deal
Mon, 23 Dec - Fri, 27 Dec
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 331Porter Airlines
Find Deal
Fri, 14 Feb - Mon, 17 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 332Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 335Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 348Porter Airlines
Find Deal
Fri, 17 Jan - Thu, 13 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 360Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 364Porter Airlines
Find Deal
Thu, 23 Jan - Mon, 27 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 401Air Transat
Find Deal
Thu, 13 Feb - Sun, 16 Feb
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 627Air Transat
Find Deal
Wed, 1 Jan - Wed, 1 Jan
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 757Air Transat
Find Deal
Sat, 19 Apr - Mon, 12 May
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 788
Find Deal
Sun, 5 Jan - Sun, 5 Jan

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
13 Feb
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Porter Airlines
13 Feb
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Porter Airlines
14 Feb
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
17 Feb
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto 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
13 Feb
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Air Transat
13 Feb
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Air Transat
13 Feb
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto 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?

In general, March 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$ 315. 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 C$ 335.

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$ 348. 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$ 424.

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 in the evening. Flights from Toronto Island Airport to Chicago Midway Airport during this time can be as low as C$ 377. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 596.

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?

The best time to book a flight to Chicago Midway Airport from Toronto Island Airport is 58 days out, which is when prices tend to be around C$ 385. Keep in mind that you might be able to find cheaper flights to Chicago Midway Airport at any time. In fact, our users found flights for as low as C$ 406 in the past 72 hours.

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

There are 1 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 60% 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

C$ 193

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 C$ 193. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 332.
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?

    Chicago Midway is 711.3 km away from Toronto Island. 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 are updated 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 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?

  • 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 C$ 288Free CancellationRating
7.9
283 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 10 times per week, with 283 momondo users rating the airline 7.9/10. 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$ 270 for Porter Airlines flights on this route.


Why use momondo?

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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