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Cheap flights from Toronto to Chicago from $136

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 10/19. 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

Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$234
Find Deal
mar., oct. 14 - mié., oct. 22
WestJet Logo
6:20 am - 10:30 amYYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
$236WestJet
Find Deal
sáb., oct. 18 - sáb., oct. 25
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
sáb., oct. 18 - sáb., oct. 25
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$241Porter Airlines
Find Deal
jue., oct. 16 - dom., oct. 19
Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$242
Find Deal
mar., oct. 14 - sáb., oct. 18
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$243Porter Airlines
Find Deal
sáb., oct. 18 - lun., oct. 20
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$244Porter Airlines
Find Deal
mar., oct. 28 - mar., nov. 4
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$272Air Transat
Find Deal
lun., oct. 13 - lun., oct. 20
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$281Air Transat
Find Deal
dom., oct. 5 - mar., oct. 7
Delta Logo
6:15 am - 12:28 pmYYZ-MDW
7h 13m1 stop
Delta Logo
11:10 am - 5:19 pmMDW-YYZ
5h 09m1 stop
$303Delta
Find Deal
jue., oct. 23 - sáb., nov. 1

Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Porter Airlines
Oct 18
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
Oct 25
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
$240
Find similar
Porter Airlines
Oct 16
YTZ3:35 pmToronto Island
1h 49m
MDW4:24 pmChicago Midway
Oct 19
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
$241
Find similar
Porter Airlines
Oct 18
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
Oct 20
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
$243
Find similar

WestJet flights from Toronto to Chicago Midway Airport

Our best WestJet deals on Toronto to Chicago Midway Airport flight tickets
WestJet
Oct 18
YYZ6:20 amToronto Pearson Intl
5h 10m
1 stop
MDW10:30 amChicago Midway
Oct 25
MDW10:35 amChicago Midway
5h 15m
1 stop
YYZ4:50 pmToronto Pearson Intl
$236
Find similar
WestJet
Oct 14
YYZ6:00 pmToronto Pearson Intl
5h 14m
1 stop
MDW10:14 pmChicago Midway
Oct 18
MDW10:35 amChicago Midway
10h 20m
1 stop
YYZ9:55 pmToronto Pearson Intl
$255
Find similar
WestJet
Oct 13
YYZ7:45 amToronto Pearson Intl
15h 29m
1 stop
MDW10:14 pmChicago Midway
Oct 21
MDW1:48 pmChicago Midway
8h 30m
1 stop
YYZ11:18 pmToronto Pearson Intl
$258
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 septiembre 15, 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

mar. 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

mié. 10/22

9:35 am-12:17 pm

Nonstop1h 42m

$234

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 10/18

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

sáb. 10/25

10:35 am-4:50 pm

1 stop5h 15m

$236

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 10/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

sáb. 10/25

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

dom. 10/19

9:35 am-12:17 pm

Nonstop1h 42m

$241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

sáb. 10/18

9:35 am-12:17 pm

Nonstop1h 42m

$242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 10/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

lun. 10/20

9:35 am-12:17 pm

Nonstop1h 42m

$243

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 10/28

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

mar. 11/4

4:15 pm-6:57 pm

Nonstop1h 42m

$244

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 10/13

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

lun. 10/20

9:35 am-12:17 pm

Nonstop1h 42m

$272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 10/5

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

mar. 10/7

5:20 pm-8:02 pm

Nonstop1h 42m

$281

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 10/23

6:15 am-12:28 pm

1 stop7h 13m

Chicago Midway

sáb. 11/1

11:10 am-5:19 pm

1 stop5h 09m

$303

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 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 $174. 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 $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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $289.

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 $270. 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

$179

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 $179. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $181.
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 49m 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
7.9
363 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 11 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 $258. Our users have rated Porter Airlines at 7.9/10.

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
Lansing
Portage
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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