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Cheap flights from Chicago Midway Airport to Toronto from $91

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 5/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Toronto

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$216Porter Airlines
Sat, Aug 8 - Sat, Aug 15
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$217Porter Airlines
Sun, Aug 9 - Wed, Aug 19
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$218Porter Airlines
Thu, Jun 18 - Thu, Jun 25
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$219Porter Airlines
Mon, May 25 - Sun, May 31
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$220Porter Airlines
Wed, Aug 12 - Mon, Aug 17
Multiple Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Multiple Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$221Multiple Airlines
Thu, May 14 - Sun, May 17
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$222Porter Airlines
Fri, May 8 - Tue, May 19
Delta Logo
9:23 am - 6:31 pm
MDW
-
YYZ
8h 08m
1 stop
Delta Logo
6:30 am - 1:19 pm
YYZ
-
MDW
7h 49m
1 stop
$268Delta
Thu, May 28 - Sun, May 31
Delta Logo
9:20 am - 5:24 pm
MDW
-
YYZ
7h 04m
1 stop
Delta Logo
12:09 pm - 6:02 pm
YYZ
-
MDW
6h 53m
1 stop
$272Delta
Sat, Jul 25 - Sat, Aug 1
Air France Logo
9:22 am - 5:21 pm
MDW
-
YYZ
6h 59m
1 stop
Air France Logo
2:20 pm - 6:33 pm
YYZ
-
MDW
5h 13m
1 stop
$281Air France
Wed, May 20 - Fri, May 22

Delta flights from Chicago Midway Airport to Toronto

Our best Delta deals on Chicago Midway Airport to Toronto flight tickets
Delta
May 28
MDW9:23 amChicago Midway
8h 08m
1 stop
YYZ6:31 pmToronto Pearson Intl
May 31
YYZ6:30 amToronto Pearson Intl
7h 49m
1 stop
MDW1:19 pmChicago Midway
$268
Delta
Jul 25
MDW9:20 amChicago Midway
7h 04m
1 stop
YYZ5:24 pmToronto Pearson Intl
Aug 1
YYZ12:09 pmToronto Pearson Intl
6h 53m
1 stop
MDW6:02 pmChicago Midway
$272
Delta
Jun 12
MDW1:49 pmChicago Midway
8h 25m
1 stop
YYZ11:14 pmToronto Pearson Intl
Jun 21
YYZ6:10 amToronto Pearson Intl
7h 26m
1 stop
MDW12:36 pmChicago Midway
$274

WestJet flights from Chicago Midway Airport to Toronto

Our best WestJet deals on Chicago Midway Airport to Toronto flight tickets
WestJet
May 27
MDW6:36 pmChicago Midway
3h 23m
1 stop
YYZ10:59 pmToronto Pearson Intl
Jun 3
YYZ9:49 amToronto Pearson Intl
3h 53m
1 stop
MDW12:42 pmChicago Midway
$425
WestJet
May 14
MDW9:22 amChicago Midway
3h 08m
1 stop
YYZ1:30 pmToronto Pearson Intl
May 17
YYZ4:04 pmToronto Pearson Intl
3h 29m
1 stop
MDW6:33 pmChicago Midway
$427
WestJet
Apr 20
MDW6:38 pmChicago Midway
3h 18m
1 stop
YYZ10:56 pmToronto Pearson Intl
Apr 21
YYZ6:10 amToronto Pearson Intl
3h 37m
1 stop
MDW8:47 amChicago Midway
$497

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 April 13, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 8/8

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Sat 8/15

8:50 am-9:40 am

Nonstop1h 50m

$216

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 8/9

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Wed 8/19

1:45 pm-2:35 pm

Nonstop1h 50m

$217

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 6/18

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Thu 6/25

1:45 pm-2:35 pm

Nonstop1h 50m

$218

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 5/25

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Sun 5/31

8:55 am-9:45 am

Nonstop1h 50m

$219

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 8/12

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Mon 8/17

8:50 am-9:40 am

Nonstop1h 50m

$220

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/14

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Sun 5/17

8:55 am-9:45 am

Nonstop1h 50m

$221

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 5/8

10:30 am-1:10 pm

Nonstop1h 40m

Toronto Island

Tue 5/19

8:55 am-9:45 am

Nonstop1h 50m

$222

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/28

9:23 am-6:31 pm

1 stop8h 08m

Toronto Pearson Intl

Sun 5/31

6:30 am-1:19 pm

1 stop7h 49m

$268

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 7/25

9:20 am-5:24 pm

1 stop7h 04m

Toronto Pearson Intl

Sat 8/1

12:09 pm-6:02 pm

1 stop6h 53m

$272

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 5/20

9:22 am-5:21 pm

1 stop6h 59m

Toronto Pearson Intl

Fri 5/22

2:20 pm-6:33 pm

1 stop5h 13m

$281

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 typical price of a round-trip flight between Chicago Midway Airport and Toronto?

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 $181. If you are unable to visit Toronto during the month of July, then departing from Chicago Midway Airport during the month January is also very affordable. Most momondo users find prices during this month for around $187.

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 Thursday. momondo users have found tickets for Thursday departures for as low as $376. 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 $671.

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 $393. 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 $688. 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?

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

$106

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Toronto

3 airports
The best one-way flight to Toronto from Chicago Midway Airport in the past 72 hours is $106. The best round-trip flight deal from Chicago Midway Airport to Toronto found on momondo in the last 72 hours is $214.
The fastest flight from Chicago Midway Airport to Toronto takes 1h 40m
Direct flights go from Chicago Midway Airport to Toronto every day.
There are 3 airports in Toronto. From Chicago Midway Airport there are direct flights to Toronto Island (YTZ).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Toronto

  • 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 40m.

  • 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
DeltaPriceFrom $88Free CancellationRating
7.9
8,407 reviews
Search Delta flights
Porter AirlinesPriceFrom $174Free CancellationRating
8.0
434 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 $174. Generally, Porter Airlines has 7 flights on this route every week with an average price of $236. Porter Airlines is rated 8.0/10 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.

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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