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Cheap flights from Toronto to Chicago Midway Airport from $106

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 Midway Airport departing on 5/4. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Toronto to Chicago.
Porter Airlines Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
5:50 pm - 8:32 pmMDW-YTZ
1h 42mnonstop
$171Porter Airlines
Find Deal
Sun, Apr 27 - Mon, May 5
Porter Airlines Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$172Porter Airlines
Find Deal
Wed, Apr 23 - Sun, Apr 27
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$207Air Transat
Find Deal
Thu, May 1 - Thu, May 8
 Logo
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
 Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Wed, Apr 30 - Wed, May 7
 Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
 Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Wed, Apr 30 - Wed, May 7
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$219Air Transat
Find Deal
Thu, Jun 5 - Wed, Jun 11
Delta Logo
6:00 am - 8:40 amYYZ-MDW
3h 40m1 stop
Delta Logo
9:20 am - 3:09 pmMDW-YYZ
4h 49m1 stop
$224Delta
Find Deal
Thu, Apr 24 - Sun, Apr 27
Delta Logo
12:54 pm - 5:19 pmYYZ-MDW
5h 25m1 stop
Delta Logo
9:16 am - 5:15 pmMDW-YYZ
6h 59m1 stop
$230Delta
Find Deal
Wed, Apr 30 - Wed, May 7
WestJet Logo
1:25 pm - 9:27 pmYYZ-MDW
9h 02m1 stop
WestJet Logo
12:48 pm - 11:55 pmMDW-YYZ
10h 07m1 stop
$290WestJet
Find Deal
Wed, May 28 - Sat, May 31
WestJet Logo
6:10 pm - 9:07 amYYZ-MDW
15h 57m1 stop
WestJet Logo
7:00 pm - 11:59 amMDW-YYZ
15h 59m1 stop
$293WestJet
Find Deal
Fri, Apr 25 - Sat, Apr 26

Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Porter Airlines
Apr 27
YTZ9:30 amToronto Island
1h 50m
MDW10:20 amChicago Midway
May 5
MDW5:50 pmChicago Midway
1h 42m
YTZ8:32 pmToronto Island
Porter Airlines
Apr 23
YTZ9:30 amToronto Island
1h 50m
MDW10:20 amChicago Midway
Apr 27
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Apr 24
YTZ9:30 amToronto Island
1h 50m
MDW10:20 amChicago Midway
Apr 27
MDW11:15 amChicago Midway
1h 42m
YTZ1:57 pmToronto Island

Air Transat flights from Toronto to Chicago Midway Airport

Our best Air Transat deals on Toronto to Chicago Midway Airport flight tickets
Air Transat
May 1
YTZ3:35 pmToronto Island
1h 49m
MDW4:24 pmChicago Midway
May 8
MDW9:40 amChicago Midway
1h 42m
YTZ12:22 pmToronto Island
Air Transat
Jun 5
YTZ7:55 amToronto Island
1h 50m
MDW8:45 amChicago Midway
Jun 11
MDW9:40 amChicago Midway
1h 42m
YTZ12:22 pmToronto Island
Air Transat
Apr 25
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
May 2
MDW5:50 pmChicago Midway
1h 42m
YTZ8:32 pmToronto Island

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto, with most prices found around $213. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Toronto during the month July is also very affordable. Most momondo users find prices during this month for around $233.

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

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Toronto. The lowest ticket price found for a Monday departure recently was $252. 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, Tuesday 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 $292.

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

Flying to Chicago Midway Airport from Toronto in the evening is the least expensive time of day to depart. momondo users have found prices as low as $252 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $284. 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.

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

As of April 2025, prices for Toronto to Chicago Midway Airport flights are approximately 23% more expensive when compared to flights at the same time last year.

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

$106

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 $106. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $171.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 49m
Direct flights go from Toronto to Chicago Midway Airport every day.

  • 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 $170Free CancellationRating
7.9
279 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 $170 round-trip, up to an average price of $261. 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
Portage
Lansing
Saint Joseph
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Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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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.


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