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Cheap flights from Toronto to Chicago from $128

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 to Chicago departing on 11/20. 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 Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$173Porter Airlines
Find Deal
Sun, Mar 8 - Wed, Mar 11
Multiple Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Multiple Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$175Multiple Airlines
Find Deal
Thu, Mar 26 - Tue, Mar 31
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$176Porter Airlines
Find Deal
Fri, Jan 23 - Sun, Jan 25
KLM Logo
6:05 am - 8:54 amYYZ-MDW
3h 49m1 stop
KLM Logo
6:48 pm - 11:05 pmMDW-YYZ
3h 17m1 stop
$203KLM
Find Deal
Thu, Nov 20 - Mon, Nov 24
KLM Logo
6:05 am - 8:54 amYYZ-MDW
3h 49m1 stop
KLM Logo
6:48 pm - 11:05 pmMDW-YYZ
3h 17m1 stop
$208KLM
Find Deal
Thu, Nov 20 - Mon, Nov 24
Delta Logo
6:05 am - 8:54 amYYZ-MDW
3h 49m1 stop
Delta Logo
6:48 pm - 11:05 pmMDW-YYZ
3h 17m1 stop
$210Delta
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Thu, Nov 20 - Sun, Nov 23
Delta Logo
6:05 am - 12:34 pmYYZ-MDW
7h 29m1 stop
Delta Logo
6:48 pm - 11:05 pmMDW-YYZ
3h 17m1 stop
$211Delta
Find Deal
Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
5:15 pm - 9:12 amYYZ-MDW
16h 57m1 stop
Multiple Airlines Logo
9:32 am - 12:11 amMDW-YYZ
13h 39m1 stop
$225Multiple Airlines
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Wed, Oct 29 - Fri, Oct 31
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$264Air Transat
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Wed, Nov 12 - Fri, Nov 14
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$268Air Transat
Find Deal
Sun, Dec 28 - Sat, Jan 3

Delta flights from Toronto to Chicago Midway Airport

Our best Delta deals on Toronto to Chicago Midway Airport flight tickets
Delta
Nov 20
YYZ6:05 amToronto Pearson Intl
3h 49m
1 stop
MDW8:54 amChicago Midway
Nov 23
MDW6:48 pmChicago Midway
3h 17m
1 stop
YYZ11:05 pmToronto Pearson Intl
$210
Find similar
Delta
Nov 20
YYZ6:05 amToronto Pearson Intl
7h 29m
1 stop
MDW12:34 pmChicago Midway
Nov 24
MDW6:48 pmChicago Midway
3h 17m
1 stop
YYZ11:05 pmToronto Pearson Intl
$211
Find similar
Delta
Nov 27
YYZ6:05 amToronto Pearson Intl
3h 49m
1 stop
MDW8:54 amChicago Midway
Nov 30
MDW1:47 pmChicago Midway
8h 34m
1 stop
YYZ11:21 pmToronto Pearson Intl
$229
Find similar

WestJet flights from Toronto to Chicago Midway Airport

Our best WestJet deals on Toronto to Chicago Midway Airport flight tickets
WestJet
Nov 8
YYZ6:20 amToronto Pearson Intl
5h 10m
1 stop
MDW10:30 amChicago Midway
Nov 9
MDW9:41 amChicago Midway
12h 40m
1 stop
YYZ11:21 pmToronto Pearson Intl
$265
Find similar
WestJet
Nov 8
YYZ6:20 amToronto Pearson Intl
5h 10m
1 stop
MDW10:30 amChicago Midway
Nov 15
MDW10:47 amChicago Midway
5h 13m
1 stop
YYZ5:00 pmToronto Pearson Intl
$268
Find similar
WestJet
Nov 12
YYZ6:30 amToronto Pearson Intl
12h 48m
1 stop
MDW6:18 pmChicago Midway
Nov 15
MDW10:47 amChicago Midway
12h 12m
1 stop
YYZ11:59 pmToronto Pearson Intl
$278
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto 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 October 16, 2025.
Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 3/8

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 3/11

11:00 am-1:42 pm

Nonstop1h 42m

$173

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 3/26

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 3/31

11:00 am-1:42 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/23

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 1/25

4:15 pm-6:57 pm

Nonstop1h 42m

$176

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/20

6:05 am-8:54 am

1 stop3h 49m

Chicago Midway

Mon 11/24

6:48 pm-11:05 pm

1 stop3h 17m

$203

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/20

6:05 am-8:54 am

1 stop3h 49m

Chicago Midway

Mon 11/24

6:48 pm-11:05 pm

1 stop3h 17m

$208

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/20

6:05 am-8:54 am

1 stop3h 49m

Chicago Midway

Sun 11/23

6:48 pm-11:05 pm

1 stop3h 17m

$210

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/20

6:05 am-12:34 pm

1 stop7h 29m

Chicago Midway

Mon 11/24

6:48 pm-11:05 pm

1 stop3h 17m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/29

5:15 pm-9:12 am

1 stop16h 57m

Chicago Midway

Fri 10/31

9:32 am-12:11 am

1 stop13h 39m

$225

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/12

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 11/14

4:15 pm-6:57 pm

Nonstop1h 42m

$264

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/28

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 1/3

4:15 pm-6:57 pm

Nonstop1h 42m

$268

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 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 and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto, with most prices found around $172. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Toronto during the month May is also very affordable. Most momondo users find prices during this month for around $206.

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. The lowest ticket price found for a Wednesday departure recently was $223. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $290.

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

Flying to Chicago Midway Airport from Toronto at noon is the least expensive time of day to depart. momondo users have found prices as low as $120 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $269. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Toronto to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago Midway flight prices

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

There are 4 cabin classes available to choose from on Toronto 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 to Chicago Midway Airport flights?

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

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

When to book flights from Toronto to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto 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 to Chicago Midway Airport (YTO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago Midway Airport

Best Price Found

$163

Fastest flight time

1h 49m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is $163. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $254.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 49m
Direct flights go from Toronto to Chicago Midway Airport every day.
Search flight deals

  • How far is Toronto to Chicago Midway by plane?

    There are 443.1 mi between Toronto and Chicago Midway. Typically, this will take 1h 50m by plane in normal conditions.

  • When did momondo last update prices for flights from Toronto to Chicago Midway Airport?

    Prices for flights from Toronto to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Toronto to Chicago Midway Airport?

  • How old do you have to be to fly from Toronto to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Toronto to Chicago Midway Airport?

  • What is the most popular airline from Toronto to Chicago Midway Airport?

Best airlines flying from Toronto to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $158Free CancellationRating
8.0
381 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Toronto to Chicago Midway Airport

    Porter Airlines is one of the most popular airlines flying from Toronto to Chicago Midway Airport, operating 12 flights/week on average for this route. A good Porter Airlines flight deal for Toronto to Chicago Midway Airport starts from $158 round-trip, up to an average price of $231. Our users have rated Porter Airlines at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Toronto to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Toronto which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Toronto to Chicago?

Once all potential Toronto to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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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