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Cheap flights from Toronto Island Airport to Chicago from $130

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 12/15. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$184Porter Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$185Porter Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$187Porter Airlines
Find Deal
Thu, Dec 4 - Fri, Dec 12
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$190Porter Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
12:45 pm - 3:27 pmMDW-YTZ
1h 42mnonstop
$192Porter Airlines
Find Deal
Mon, Feb 9 - Sat, Feb 28
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$193Porter Airlines
Find Deal
Wed, Nov 19 - Fri, Nov 21
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$194Porter Airlines
Find Deal
Tue, Dec 9 - Fri, Dec 12
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$201Air Transat
Find Deal
Sun, Nov 16 - Wed, Nov 19
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$221Air Transat
Find Deal
Fri, Nov 14 - Sun, Nov 16
Multiple Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Multiple Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$230Multiple Airlines
Find Deal
Thu, Nov 20 - Fri, Nov 21

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
Nov 21
YTZ2:30 pmToronto Island
1h 50m
MDW3:20 pmChicago Midway
Nov 23
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$184
Find similar
Porter Airlines
Nov 21
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Nov 23
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$185
Find similar
Porter Airlines
Dec 4
YTZ2:30 pmToronto Island
1h 50m
MDW3:20 pmChicago Midway
Dec 12
MDW4:15 pmChicago Midway
1h 42m
YTZ6:57 pmToronto Island
$187
Find similar

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
Nov 16
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Nov 19
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$201
Find similar
Air Transat
Nov 14
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Nov 16
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$221
Find similar
Air Transat
Nov 13
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Nov 16
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$322
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 2, 2025.
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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/21

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 11/23

11:00 am-1:42 pm

Nonstop1h 42m

$184

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/21

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 11/23

11:00 am-1:42 pm

Nonstop1h 42m

$185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/4

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Fri 12/12

4:15 pm-6:57 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/12

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 12/14

4:15 pm-6:57 pm

Nonstop1h 42m

$190

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 2/28

12:45 pm-3:27 pm

Nonstop1h 42m

$192

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/19

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 11/21

11:00 am-1:42 pm

Nonstop1h 42m

$193

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 12/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 12/12

4:15 pm-6:57 pm

Nonstop1h 42m

$194

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 11/19

11:00 am-1:42 pm

Nonstop1h 42m

$201

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 11/16

11:00 am-1:42 pm

Nonstop1h 42m

$221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 11/21

11:00 am-1:42 pm

Nonstop1h 42m

$230

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

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 to Chicago Midway Airport?

The month of July is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto Island Airport, with most prices found around $182. If you are unable to visit Chicago Midway Airport during the month of July, then departing from Toronto Island Airport during the month September is also very affordable. Most momondo users find prices during this month for around $182.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Toronto Island Airport. The lowest ticket price found for a Saturday 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, Thursday 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 $291.

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 $242 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $333. 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

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

There are 4 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.

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

$189

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 $189. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is $286.
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

  • 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 $158Free CancellationRating
8.0
384 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 $231, with the best Porter Airlines deals starting from $158 round-trip. 384 users have rated Porter Airlines on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
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Saint John

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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