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Cheap flights from Chicago Midway Airport to Toronto from $81

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Toronto departing on 10/18. 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 Chicago Midway Airport to Toronto

Cheap round-trip flights

Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
12:00 pm - 9:47 amYTZ-MDW
22h 47m2 stops
$230Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$244Porter Airlines
Find Deal
Sat, Oct 18 - Mon, Oct 20
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
7:30 pm - 11:25 pmYTZ-MDW
28h 55m1 stop
$246Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$248Porter Airlines
Find Deal
Mon, Oct 20 - Fri, Oct 24
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
$249Multiple Airlines
Find Deal
Mon, Oct 6 - Tue, Oct 7
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$250Porter Airlines
Find Deal
Wed, Oct 15 - Thu, Oct 16
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$252Porter Airlines
Find Deal
Sat, Oct 18 - Sun, Oct 19
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$254Porter Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 15
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$255Porter Airlines
Find Deal
Tue, Oct 7 - Wed, Oct 8
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$256Porter Airlines
Find Deal
Mon, Oct 6 - Tue, Oct 7

Porter Airlines flights from Chicago Midway Airport to Toronto Island Airport

Our best Porter Airlines deals on Chicago Midway Airport to Toronto Island Airport flight tickets
Porter Airlines
Oct 18
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
Oct 20
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
$244
Find similar
Porter Airlines
Oct 20
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
Oct 24
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
$248
Find similar
Porter Airlines
Oct 15
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
Oct 16
YTZ3:35 pmToronto Island
1h 49m
MDW4:24 pmChicago Midway
$250
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Toronto Island 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Island Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/22

12:00 pm-9:47 am

2 stops22h 47m

$230

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/18

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Mon 10/20

7:50 am-8:39 am

Nonstop1h 49m

$244

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/22

7:30 pm-11:25 pm

1 stop28h 55m

$246

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 10/20

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Fri 10/24

7:50 am-8:39 am

Nonstop1h 49m

$248

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 10/6

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:30 pm-11:25 pm

1 stop4h 55m

$249

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

$250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/18

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/19

3:35 pm-4:24 pm

Nonstop1h 49m

$252

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/15

3:35 pm-4:24 pm

Nonstop1h 49m

$254

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 10/7

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/8

7:50 am-8:39 am

Nonstop1h 49m

$255

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 10/6

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

3:35 pm-4:24 pm

Nonstop1h 49m

$256

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 Toronto from

How to get the cheapest flight ticket from Chicago Midway Airport to Toronto Island 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 Toronto Island Airport?

If you aren’t able to travel during the month of July, then book flights to Toronto Island Airport from Chicago Midway Airport during June instead. Flights to Toronto Island Airport in June, while not as cheap as those in July, still average around $192.

What is the cheapest day to depart on your flight to Toronto Island Airport?

The cheapest day to depart on your flight to Toronto Island Airport is on a Saturday when prices can be found for as low as $263. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $334. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.

What is the cheapest time of day to depart on your flight to Toronto Island Airport?

Our data shows that the cheapest Chicago Midway Airport to Toronto Island Airport flights are usually those with departure times in the afternoon. Our users have found flights to Toronto Island Airport in the afternoon for as low as $273. In contrast, the most expensive time of day to depart to Toronto Island Airport is in the evening when prices are around $311.

What is the cheapest Chicago Midway to Toronto Island flight route?

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

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

There are 3 cabin classes available to choose from on Chicago Midway to Toronto Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of September 2025, prices for Chicago Midway Airport to Toronto Island Airport flights are approximately 15% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Toronto Island Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Toronto Island Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Toronto Island Airport (MDW to YTZ) flight deals and tips

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

Best Price Found

$88

Fastest flight time

1h 42m

Direct flights

Every day
The best one-way flight to Toronto Island Airport from Chicago Midway Airport in the past 72 hours is $88. The best round-trip flight deal from Chicago Midway Airport to Toronto Island Airport found on momondo in the last 72 hours is $196.
The fastest flight from Chicago Midway Airport to Toronto Island Airport takes 1h 42m
Direct flights go from Chicago Midway Airport to Toronto Island Airport every day.
Search flight deals

  • How far is Chicago Midway to Toronto Island by plane?

    The straight-line distance from Chicago Midway to Toronto Island is 442.0 mi. In terms of flight time, this usually takes a little over 1h 42m.

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

    Prices for flights from Chicago Midway Airport to Toronto Island Airport are refreshed on a daily basis.

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

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

  • What documentation or ID do you need to fly to Toronto Island Airport?

    The travel and health documents you'll need for your trip to Toronto Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Toronto Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Chicago Midway Airport to Toronto Island Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Toronto Island Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $187Free CancellationRating
7.9
365 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Chicago Midway Airport to Toronto Island Airport

    Porter Airlines operates around 11 flights from Chicago Midway Airport to Toronto Island Airport every week. The average price of these flights found in the last 72 hours has been $257, but momondo users have found Porter Airlines deals from Chicago Midway Airport to Toronto Island Airport from as low as $187 round-trip. Porter Airlines has been scored 7.9/10 in 365 reviews.

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Toronto for you.

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

All flight searches from Chicago to Toronto on momondo can be filtered to show those which offer flexible booking policies.

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

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 Chicago to Toronto.

I’m not ready to book a flight from Chicago to Toronto right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Toronto, momondo offers a useful price alert feature which will track prices for flights to Toronto from Chicago and alert you when they change.

An easier way to manage your Toronto Island Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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