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Cheap flights from Chicago Midway Airport to Toronto from $89

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 9/4. 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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Find the cheapest flights from Chicago Midway Airport to Toronto (MDW-YYZ)

Cheap round-trip flights

Delta Logo
9:30 am - 1:32 pmMDW-YYZ
3h 02m1 stop
Delta Logo
12:15 pm - 6:35 pmYYZ-MDW
7h 20m1 stop
$233Delta
Find Deal
Wed, Sep 10 - Fri, Sep 12
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
Delta Logo
6:00 am - 1:03 pmYYZ-MDW
8h 03m1 stop
$272Delta
Find Deal
Wed, Sep 17 - Wed, Sep 24
Delta Logo
1:43 pm - 11:33 pmMDW-YYZ
8h 50m1 stop
Delta Logo
6:30 am - 12:28 pmYYZ-MDW
6h 58m1 stop
$300Delta
Find Deal
Tue, Aug 26 - Sat, Aug 30
WestJet Logo
9:20 am - 11:20 pmMDW-YYZ
13h 00m1 stop
WestJet Logo
11:36 am - 9:36 pmYYZ-MDW
11h 00m1 stop
$302WestJet
Find Deal
Wed, Sep 24 - Sun, Sep 28
WestJet Logo
10:31 am - 4:57 pmMDW-YYZ
5h 26m1 stop
WestJet Logo
1:20 pm - 9:26 pmYYZ-MDW
9h 06m1 stop
$311WestJet
Find Deal
Sat, Sep 6 - Sun, Sep 7
WestJet Logo
12:43 pm - 9:51 pmMDW-YYZ
8h 08m1 stop
WestJet Logo
12:30 pm - 5:35 pmYYZ-MDW
6h 05m1 stop
$312WestJet
Find Deal
Tue, Sep 23 - Tue, Sep 30
WestJet Logo
7:10 pm - 6:30 pmMDW-YYZ
22h 20m1 stop
WestJet Logo
1:20 pm - 9:40 amYYZ-MDW
21h 20m1 stop
$330WestJet
Find Deal
Mon, Oct 6 - Tue, Oct 14
WestJet Logo
12:48 pm - 11:58 pmMDW-YYZ
10h 10m1 stop
WestJet Logo
11:52 am - 10:14 pmYYZ-MDW
11h 22m1 stop
$336WestJet
Find Deal
Mon, Oct 6 - Tue, Oct 14
WestJet Logo
10:31 am - 10:23 amMDW-YYZ
22h 52m1 stop
WestJet Logo
6:20 am - 5:37 pmYYZ-MDW
12h 17m1 stop
$341WestJet
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
6:17 pm - 10:58 pmMDW-YYZ
3h 41m1 stop
Delta Logo
6:30 am - 8:35 amYYZ-MDW
3h 05m1 stop
$342Delta
Find Deal
Wed, Aug 20 - Wed, Aug 27

WestJet flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best WestJet deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets
WestJet
Sep 24
MDW9:20 amChicago Midway
13h 00m
1 stop
YYZ11:20 pmToronto Pearson Intl
Sep 28
YYZ11:36 amToronto Pearson Intl
11h 00m
1 stop
MDW9:36 pmChicago Midway
$302
Find similar
WestJet
Sep 6
MDW10:31 amChicago Midway
5h 26m
1 stop
YYZ4:57 pmToronto Pearson Intl
Sep 7
YYZ1:20 pmToronto Pearson Intl
9h 06m
1 stop
MDW9:26 pmChicago Midway
$311
Find similar
WestJet
Sep 23
MDW12:43 pmChicago Midway
8h 08m
1 stop
YYZ9:51 pmToronto Pearson Intl
Sep 30
YYZ12:30 pmToronto Pearson Intl
6h 05m
1 stop
MDW5:35 pmChicago Midway
$312
Find similar

Delta flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best Delta deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets
Delta
Sep 10
MDW9:30 amChicago Midway
3h 02m
1 stop
YYZ1:32 pmToronto Pearson Intl
Sep 12
YYZ12:15 pmToronto Pearson Intl
7h 20m
1 stop
MDW6:35 pmChicago Midway
$233
Find similar
Delta
Sep 17
MDW9:35 amChicago Midway
6h 48m
1 stop
YYZ5:23 pmToronto Pearson Intl
Sep 24
YYZ6:00 amToronto Pearson Intl
8h 03m
1 stop
MDW1:03 pmChicago Midway
$272
Find similar
Delta
Aug 26
MDW1:43 pmChicago Midway
8h 50m
1 stop
YYZ11:33 pmToronto Pearson Intl
Aug 30
YYZ6:30 amToronto Pearson Intl
6h 58m
1 stop
MDW12:28 pmChicago Midway
$300
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Toronto Pearson Intl 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 August 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Pearson Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 9/10

9:30 am-1:32 pm

1 stop3h 02m

Toronto Pearson Intl

Fri 9/12

12:15 pm-6:35 pm

1 stop7h 20m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 9/17

9:35 am-5:23 pm

1 stop6h 48m

Toronto Pearson Intl

Wed 9/24

6:00 am-1:03 pm

1 stop8h 03m

$272

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 8/26

1:43 pm-11:33 pm

1 stop8h 50m

Toronto Pearson Intl

Sat 8/30

6:30 am-12:28 pm

1 stop6h 58m

$300

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 9/24

9:20 am-11:20 pm

1 stop13h 00m

Toronto Pearson Intl

Sun 9/28

11:36 am-9:36 pm

1 stop11h 00m

$302

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 9/6

10:31 am-4:57 pm

1 stop5h 26m

Toronto Pearson Intl

Sun 9/7

1:20 pm-9:26 pm

1 stop9h 06m

$311

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/23

12:43 pm-9:51 pm

1 stop8h 08m

Toronto Pearson Intl

Tue 9/30

12:30 pm-5:35 pm

1 stop6h 05m

$312

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 10/6

7:10 pm-6:30 pm

1 stop22h 20m

Toronto Pearson Intl

Tue 10/14

1:20 pm-9:40 am

1 stop21h 20m

$330

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 10/6

12:48 pm-11:58 pm

1 stop10h 10m

Toronto Pearson Intl

Tue 10/14

11:52 am-10:14 pm

1 stop11h 22m

$336

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 8/27

10:31 am-10:23 am

1 stop22h 52m

Toronto Pearson Intl

Wed 9/3

6:20 am-5:37 pm

1 stop12h 17m

$341

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 8/20

6:17 pm-10:58 pm

1 stop3h 41m

Toronto Pearson Intl

Wed 8/27

6:30 am-8:35 am

1 stop3h 05m

$342

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 Pearson Intl 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 day to depart on your flight to Toronto Pearson Intl Airport?

The cheapest day to depart from Chicago Midway Airport to Toronto Pearson Intl Airport is on a Thursday when prices can be found for as low as $622. The most expensive day to fly to Toronto Pearson Intl Airport is Sunday, with ticket prices averaging around $767.

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

Flying to Toronto Pearson Intl Airport from Chicago Midway Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $556 when looking at flights departing in the morning. Flights in the afternoon are often more expensive with an average ticket price of $763.

When to book flights from Chicago Midway Airport to Toronto Pearson Intl Airport

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

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

Best Price Found

$89

Fastest flight time

3h 02m

Direct flights

None
The best one-way flight to Toronto Pearson Intl Airport from Chicago Midway Airport in the past 72 hours is $89. The best round-trip flight deal from Chicago Midway Airport to Toronto Pearson Intl Airport found on momondo in the last 72 hours is $233.
The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 02m
There are no direct flights from Chicago Midway Airport to Toronto Pearson Intl Airport. Popular non-direct route for this connection is Chicago Midway Airport - Toronto Pearson Intl Airport.
Search flight deals

  • How far is Chicago Midway to Toronto Pearson Intl by plane?

    The distance between Chicago Midway and Toronto Pearson Intl is about 432.2 mi. A reasonable flight in good conditions will take 3h 02m.

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

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

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

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

    The travel and health documents you'll need for your trip to Toronto Pearson Intl 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 Pearson Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Toronto?

Book flights to Toronto if you plan to visit one of these locations
Niagara Falls
Mississauga
Niagara-on-the-Lake
Brampton
Markham
Vaughan
Richmond Hill
Oakville
Burlington
Kitchener
Cambridge
Guelph
Barrie
St. Catharines
Milton
Brantford
Oshawa
Waterloo
Orillia
Collingwood

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Toronto. momondo saves you time and could save you money on your trip.

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 all potential Chicago to Toronto 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 Chicago to Toronto right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Toronto from Chicago. 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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