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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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0 bags

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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
Multiple Airlines Logo
9:32 am - 8:00 pmMDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
12:50 pm - 10:20 pmYYZ-MDW
10h 30m1 stop
$241Multiple Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Multiple Airlines Logo
9:32 am - 8:00 pmMDW-YYZ
9h 28m1 stop
Multiple Airlines Logo
12:50 pm - 10:20 pmYYZ-MDW
10h 30m1 stop
$243Multiple Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
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
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
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
WestJet Logo
9:20 am - 3:59 pmMDW-YYZ
5h 39m1 stop
WestJet Logo
6:20 am - 1:08 pmYYZ-MDW
7h 48m1 stop
$277WestJet
Find Deal
Sat, Nov 1 - Sat, Nov 8
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
$289WestJet
Find Deal
Sat, Oct 18 - Sun, Oct 19
WestJet Logo
9:20 am - 6:13 amMDW-YYZ
19h 53m2 stops
WestJet Logo
7:24 pm - 5:43 pmYYZ-MDW
23h 19m1 stop
$292WestJet
Find Deal
Tue, Oct 14 - Thu, Oct 16

WestJet flights from Chicago Midway Airport to Toronto

Our best WestJet deals on Chicago Midway Airport to Toronto flight tickets
WestJet
Nov 1
MDW9:20 amChicago Midway
5h 39m
1 stop
YYZ3:59 pmToronto Pearson Intl
Nov 8
YYZ6:20 amToronto Pearson Intl
7h 48m
1 stop
MDW1:08 pmChicago Midway
$277
Find similar
WestJet
Oct 18
MDW10:35 amChicago Midway
5h 15m
1 stop
YYZ4:50 pmToronto Pearson Intl
Oct 19
YYZ6:00 pmToronto Pearson Intl
5h 14m
1 stop
MDW10:14 pmChicago Midway
$289
Find similar
WestJet
Oct 14
MDW9:20 amChicago Midway
19h 53m
2 stops
YYZ6:13 amToronto Pearson Intl
Oct 16
YYZ7:24 pmToronto Pearson Intl
23h 19m
1 stop
MDW5:43 pmChicago Midway
$292
Find similar

Delta flights from Chicago Midway Airport to Toronto

Our best Delta deals on Chicago Midway Airport to Toronto flight tickets
Delta
Sep 23
MDW1:08 pmChicago Midway
3h 15m
1 stop
YYZ5:23 pmToronto Pearson Intl
Sep 29
YYZ4:12 pmToronto Pearson Intl
3h 23m
1 stop
MDW6:35 pmChicago Midway
$561
Find similar
Delta
Sep 23
MDW1:08 pmChicago Midway
3h 15m
1 stop
YYZ5:23 pmToronto Pearson Intl
Sep 30
YYZ4:12 pmToronto Pearson Intl
3h 23m
1 stop
MDW6:35 pmChicago Midway
$588
Find similar
Delta
Sep 24
MDW9:35 amChicago Midway
4h 47m
1 stop
YYZ3:22 pmToronto Pearson Intl
Sep 27
YYZ12:30 pmToronto Pearson Intl
6h 05m
1 stop
MDW5:35 pmChicago Midway
$645
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Toronto 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 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 - YYZ

MDWYYZ

Chicago Midway

Fri 10/31

9:32 am-8:00 pm

1 stop9h 28m

Toronto Pearson Intl

Fri 11/7

12:50 pm-10:20 pm

1 stop10h 30m

$241

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 10/31

9:32 am-8:00 pm

1 stop9h 28m

Toronto Pearson Intl

Fri 11/7

12:50 pm-10:20 pm

1 stop10h 30m

$243

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

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

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 - YYZ

MDWYYZ

Chicago Midway

Sat 11/1

9:20 am-3:59 pm

1 stop5h 39m

Toronto Pearson Intl

Sat 11/8

6:20 am-1:08 pm

1 stop7h 48m

$277

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 10/18

10:35 am-4:50 pm

1 stop5h 15m

Toronto Pearson Intl

Sun 10/19

6:00 pm-10:14 pm

1 stop5h 14m

$289

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 10/14

9:20 am-6:13 am

2 stops19h 53m

Toronto Pearson Intl

Thu 10/16

7:24 pm-5:43 pm

1 stop23h 19m

$292

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

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?

The month of July is, on average, the cheapest month to fly to Toronto from Chicago Midway Airport, with most prices found around $179. If you are unable to visit Toronto during the month of July, then departing from Chicago Midway Airport during the month August is also very affordable. Most momondo users find prices during this month for around $197.

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

On average, the least expensive day to fly to Toronto from Chicago Midway Airport is on a Friday. momondo users have found tickets for Friday departures for as low as $475. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Toronto is Sunday, with ticket prices averaging around $687.

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

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Toronto when you can find flight prices for as low as $456. Flying to Toronto in the morning is an ideal time because this is during off-peak travel hours. Flights to Toronto are more costly in the afternoon, with an average ticket price of $711. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Toronto flight route?

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

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

There are 3 cabin classes available to choose from on Chicago Midway to Toronto 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 Chicago Midway Airport to Toronto flights?

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

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

As of September 2025, prices for Chicago Midway Airport to Toronto flights are approximately 73% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Toronto

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

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

Best Price Found

$88

Fastest flight time

1h 42m

Direct flights

Every day

Airports in Toronto

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

  • How far is Chicago Midway to Toronto by plane?

    Toronto is 443.1 mi away from Chicago Midway. 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?

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

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

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

    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.

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

    The travel and health documents you'll need for your trip to Toronto 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. 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?

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

Best airlines flying from Chicago Midway Airport to Toronto

Compare and see reviews for airlines that fly from Chicago Midway Airport to Toronto 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

    The lowest priced Porter Airlines flight from Chicago Midway Airport to Toronto from the last 72 hours was $187. Generally, Porter Airlines has 11 flights on this route every week with an average price of $257. Porter Airlines is rated 7.9/10 by our users.

Why use momondo?

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

It is quick and easy to find Chicago to Toronto flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Toronto that suits you.

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

Yes. All flights to Toronto from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Toronto from Chicago.

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

If you are not ready to book a flight from Chicago to Toronto now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Toronto and let you know when they change.

An easier way to manage your Toronto 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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Fri 10/17
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Find better results for your trip to Canada

Fly into one of these airports located in Toronto

Airports listed have a maximum distance of 52.0 mi from Toronto
Toronto Region of Waterloo Intl Airport
Toronto Island Airport
Toronto Pearson Intl Airport