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Cheap flights from Toronto Island Airport to Chicago Midway Airport from $133

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 12/14. 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.
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$237Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$239Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
Sun, Dec 15 - Sun, Jan 5
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$262Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$271Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$275Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:15 am - 4:58 pmMDW-YTZ
10h 43m2 stops
Fri, Dec 6 - Sun, Dec 8
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$133Porter Airlines
Find Deal
Sat, Dec 14
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$136Porter Airlines
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Thu, Dec 19
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$138Porter Airlines
Find Deal
Thu, Dec 12
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
$141Porter Airlines
Find Deal
Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$142Porter Airlines
Find Deal
Thu, Dec 12
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$143Porter Airlines
Find Deal
Sat, Dec 14
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
$147Porter Airlines
Find Deal
Sat, Jan 4
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$148Porter Airlines
Find Deal
Sun, Jan 19
8:55 pm - 11:11 amYTZ-MDW
15h 16m1 stop
Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$203Air Transat
Find Deal
Sat, Dec 21
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$438Porter Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$445Porter Airlines
Find Deal
Sun, Nov 24 - Sat, Nov 30
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$450Porter Airlines
Find Deal
Sat, Nov 23 - Tue, Dec 3
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$452Porter Airlines
Find Deal
Sat, Nov 23 - Sun, Dec 1
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$457Porter Airlines
Find Deal
Mon, Nov 25 - Fri, Nov 29
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$471Porter Airlines
Find Deal
Thu, Nov 21 - Thu, Nov 28
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$490Porter Airlines
Find Deal
Fri, Nov 22 - Sat, Nov 30
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$491Air Transat
Find Deal
Sun, Nov 24 - Thu, Nov 28
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$497Porter Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
Mon, Nov 25 - Sat, Nov 30
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$237Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$239Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
Fri, Dec 13 - Fri, Dec 20
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$262Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$271Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$275Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
Sat, Nov 30 - Sat, Jan 18

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
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 15
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Dec 13
YTZ10:20 amToronto Island
1h 50m
MDW11:10 amChicago Midway
Dec 17
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 16
MDW12:05 pmChicago Midway
1h 42m
YTZ2:47 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
Dec 12
YTZ9:40 amToronto Island
1h 50m
MDW10:30 amChicago Midway
Dec 15
MDW11:15 amChicago Midway
1h 42m
YTZ1:57 pmToronto Island
Air Transat
Dec 12
YTZ9:40 amToronto Island
1h 50m
MDW10:30 amChicago Midway
Dec 15
MDW11:15 amChicago Midway
1h 42m
YTZ1:57 pmToronto Island
Air Transat
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 15
MDW11:15 amChicago Midway
1h 42m
YTZ1:57 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 cheapest month to fly from Toronto Island Airport to Chicago Midway Airport?

January. The cheapest time of year to fly to Chicago Midway Airport from Toronto Island Airport is January. Most expensive is November

What is the cheapest day to depart Toronto Island Airport for Chicago Midway Airport?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Toronto Island Airport to Chicago Midway Airport?

In the evening. Toronto Island Airport to Chicago Midway Airport flights are approximately 4% more expensive in the morning than in the evening

How far in advance should you book Toronto Island Airport to Chicago Midway Airport flights?

40 days before. The cheapest time to buy a flight from Toronto Island Airport to Chicago Midway Airport is approximately 40 days to departure

Can stopping save me money on Toronto Island Airport to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Toronto Island Airport to Chicago Midway Airport.

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

As of November 2024, prices for Toronto Island Airport to Chicago Midway Airport flights are approximately 2% cheaper 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

$133

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 $133. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is $219.
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.

  • 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 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 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 $205Free CancellationRating
7.8
286 reviews
Search Porter Airlines flights
  • Porter Airlines Flights From Toronto Island Airport to Chicago Midway Airport

    Across 9 Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport this week, the average price was $254, with the best Porter Airlines deals starting from $205 round-trip. 286 users have rated Porter Airlines on momondo, with an average score of 7.8/10.


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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