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Cheap flights from Chicago Midway Airport to Toronto from $96

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 12/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

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Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$187Porter Airlines
Find Deal
Tue, Jan 6 - Thu, Jan 8
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$189Porter Airlines
Find Deal
Mon, Jan 5 - Mon, Jan 12
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$190Porter Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$191Porter Airlines
Find Deal
Tue, Jan 6 - Mon, Jan 12
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$192Porter Airlines
Find Deal
Mon, Jan 5 - Thu, Jan 8
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$194Porter Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
4:21 pm - 2:20 pmMDW-YYZ
20h 59m1 stop
Multiple Airlines Logo
7:10 am - 10:59 pmYYZ-MDW
16h 49m1 stop
$223Multiple Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 11
Delta Logo
6:14 pm - 10:41 pmMDW-YYZ
3h 27m1 stop
Delta Logo
6:00 am - 8:52 amYYZ-MDW
3h 52m1 stop
$233Delta
Find Deal
Thu, Jan 8 - Sun, Jan 11
Delta Logo
6:14 pm - 10:41 pmMDW-YYZ
3h 27m1 stop
Delta Logo
6:00 am - 8:52 amYYZ-MDW
3h 52m1 stop
$240Delta
Find Deal
Thu, Jan 8 - Sun, Jan 11
Delta Logo
6:14 pm - 10:41 pmMDW-YYZ
3h 27m1 stop
Delta Logo
6:00 am - 8:52 amYYZ-MDW
3h 52m1 stop
$241Delta
Find Deal
Thu, Jan 8 - Sun, Jan 11

Delta flights from Chicago Midway Airport to Toronto

Our best Delta deals on Chicago Midway Airport to Toronto flight tickets
Delta
Jan 8
MDW1:28 pmChicago Midway
8h 13m
1 stop
YYZ10:41 pmToronto Pearson Intl
Jan 11
YYZ6:00 amToronto Pearson Intl
3h 52m
1 stop
MDW8:52 amChicago Midway
$233
Find similar
Delta
Jan 8
MDW6:14 pmChicago Midway
3h 27m
1 stop
YYZ10:41 pmToronto Pearson Intl
Jan 11
YYZ6:00 amToronto Pearson Intl
3h 52m
1 stop
MDW8:52 amChicago Midway
$240
Find similar
Delta
Jan 8
MDW6:14 pmChicago Midway
3h 27m
1 stop
YYZ10:41 pmToronto Pearson Intl
Jan 11
YYZ10:05 amToronto Pearson Intl
8h 32m
1 stop
MDW5:37 pmChicago Midway
$241
Find similar

WestJet flights from Chicago Midway Airport to Toronto

Our best WestJet deals on Chicago Midway Airport to Toronto flight tickets
WestJet
Dec 22
MDW11:48 amChicago Midway
10h 32m
1 stop
YYZ11:20 pmToronto Pearson Intl
Dec 31
YYZ6:00 amToronto Pearson Intl
6h 06m
1 stop
MDW11:06 amChicago Midway
$301
Find similar
WestJet
Jan 8
MDW11:21 amChicago Midway
11h 37m
1 stop
YYZ11:58 pmToronto Pearson Intl
Jan 11
YYZ6:30 amToronto Pearson Intl
13h 02m
1 stop
MDW6:32 pmChicago Midway
$313
Find similar
WestJet
Dec 13
MDW1:50 pmChicago Midway
8h 37m
1 stop
YYZ11:27 pmToronto Pearson Intl
Dec 14
YYZ6:12 pmToronto Pearson Intl
16h 42m
1 stop
MDW9:54 amChicago Midway
$314
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 November 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

Tue 1/6

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 1/8

9:15 am-10:05 am

Nonstop1h 50m

$187

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 1/5

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 1/12

9:15 am-10:05 am

Nonstop1h 50m

$189

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 12/11

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 12/14

9:15 am-10:05 am

Nonstop1h 50m

$190

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 1/6

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 1/12

9:15 am-10:05 am

Nonstop1h 50m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 1/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Thu 1/8

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$194

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 1/9

4:21 pm-2:20 pm

1 stop20h 59m

Toronto Pearson Intl

Sun 1/11

7:10 am-10:59 pm

1 stop16h 49m

$223

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 1/8

6:14 pm-10:41 pm

1 stop3h 27m

Toronto Pearson Intl

Sun 1/11

6:00 am-8:52 am

1 stop3h 52m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 1/8

6:14 pm-10:41 pm

1 stop3h 27m

Toronto Pearson Intl

Sun 1/11

6:00 am-8:52 am

1 stop3h 52m

$240

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 1/8

6:14 pm-10:41 pm

1 stop3h 27m

Toronto Pearson Intl

Sun 1/11

6:00 am-8:52 am

1 stop3h 52m

$241

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 $473. 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 $699.

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 $475. 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 $712. 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 November 2025, prices for Chicago Midway Airport to Toronto flights are approximately 4% more expensive 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

$210

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 $210. The best round-trip flight deal from Chicago Midway Airport to Toronto found on momondo in the last 72 hours is $287.
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 $185Free CancellationRating
8.0
392 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 $185. Generally, Porter Airlines has 11 flights on this route every week with an average price of $234. 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.

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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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