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Cheap flights from Chicago Midway Airport to Toronto from $122

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 6/20. 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

Enter your travel dates to find the best prices.
Delta Logo
6:36 pm - 10:59 pm
MDW
-
YYZ
3h 23m
1 stop
Delta Logo
6:10 am - 8:43 am
YYZ
-
MDW
3h 33m
1 stop
$304Delta
Sat, May 30 - Mon, Jun 1
Delta Logo
9:17 am - 1:34 pm
MDW
-
YYZ
3h 17m
1 stop
Delta Logo
6:05 am - 9:14 am
YYZ
-
MDW
4h 09m
1 stop
$324Delta
Wed, Jun 24 - Tue, Jun 30
Delta Logo
1:26 pm - 11:02 pm
MDW
-
YYZ
8h 36m
1 stop
Delta Logo
6:05 am - 12:46 pm
YYZ
-
MDW
7h 41m
1 stop
$344Delta
Fri, Jun 26 - Mon, Jun 29
Delta Logo
6:35 pm - 11:02 pm
MDW
-
YYZ
3h 27m
1 stop
Delta Logo
6:10 am - 12:38 pm
YYZ
-
MDW
7h 28m
1 stop
$345Delta
Sat, Jul 11 - Sun, Jul 26
Delta Logo
9:17 am - 1:34 pm
MDW
-
YYZ
3h 17m
1 stop
Delta Logo
6:05 am - 9:14 am
YYZ
-
MDW
4h 09m
1 stop
$352Delta
Wed, Jun 24 - Wed, Jul 1
Delta Logo
1:00 pm - 5:23 pm
MDW
-
YYZ
3h 23m
1 stop
Delta Logo
6:00 am - 12:30 pm
YYZ
-
MDW
7h 30m
1 stop
$353Delta
Tue, Sep 15 - Thu, Sep 17
Delta Logo
9:22 am - 5:21 pm
MDW
-
YYZ
6h 59m
1 stop
Delta Logo
6:05 am - 9:14 am
YYZ
-
MDW
4h 09m
1 stop
$360Delta
Thu, Jun 4 - Mon, Jun 8
Delta Logo
9:22 am - 5:21 pm
MDW
-
YYZ
6h 59m
1 stop
Delta Logo
6:05 am - 9:14 am
YYZ
-
MDW
4h 09m
1 stop
$362Delta
Thu, Jun 4 - Mon, Jun 8
Delta Logo
9:22 am - 5:21 pm
MDW
-
YYZ
6h 59m
1 stop
Delta Logo
12:09 pm - 6:33 pm
YYZ
-
MDW
7h 24m
1 stop
$363Delta
Thu, May 28 - Sun, May 31
WestJet Logo
9:22 am - 5:29 pm
MDW
-
YYZ
7h 07m
1 stop
WestJet Logo
2:34 pm - 6:36 pm
YYZ
-
MDW
5h 02m
1 stop
$364WestJet
Tue, Jun 9 - Tue, Jun 16

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
Jun 9
MDW9:22 amChicago Midway
7h 07m
1 stop
YYZ5:29 pmToronto Pearson Intl
Jun 16
YYZ2:34 pmToronto Pearson Intl
5h 02m
1 stop
MDW6:36 pmChicago Midway
$364
WestJet
Jul 28
MDW12:41 pmChicago Midway
20h 44m
1 stop
YYZ10:25 amToronto Pearson Intl
Jul 29
YYZ2:24 pmToronto Pearson Intl
5h 01m
1 stop
MDW6:25 pmChicago Midway
$459
WestJet
Jun 12
MDW1:26 pmChicago Midway
24h 53m
1 stop
YYZ3:19 pmToronto Pearson Intl
Jun 13
YYZ6:34 pmToronto Pearson Intl
16h 35m
1 stop
MDW10:09 amChicago Midway
$464

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
May 30
MDW6:36 pmChicago Midway
3h 23m
1 stop
YYZ10:59 pmToronto Pearson Intl
Jun 1
YYZ6:10 amToronto Pearson Intl
3h 33m
1 stop
MDW8:43 amChicago Midway
$304
Delta
Jun 24
MDW9:17 amChicago Midway
7h 07m
1 stop
YYZ5:24 pmToronto Pearson Intl
Jun 28
YYZ6:05 amToronto Pearson Intl
7h 41m
1 stop
MDW12:46 pmChicago Midway
$324
Delta
Jun 26
MDW1:26 pmChicago Midway
8h 36m
1 stop
YYZ11:02 pmToronto Pearson Intl
Jun 29
YYZ6:05 amToronto Pearson Intl
7h 41m
1 stop
MDW12:46 pmChicago Midway
$344

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 May 13, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 5/30

6:36 pm-10:59 pm

1 stop3h 23m

Toronto Pearson Intl

Mon 6/1

6:10 am-8:43 am

1 stop3h 33m

$304

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 6/24

9:17 am-1:34 pm

1 stop3h 17m

Toronto Pearson Intl

Tue 6/30

6:05 am-9:14 am

1 stop4h 09m

$324

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 6/26

1:26 pm-11:02 pm

1 stop8h 36m

Toronto Pearson Intl

Mon 6/29

6:05 am-12:46 pm

1 stop7h 41m

$344

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 7/11

6:35 pm-11:02 pm

1 stop3h 27m

Toronto Pearson Intl

Sun 7/26

6:10 am-12:38 pm

1 stop7h 28m

$345

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 6/24

9:17 am-1:34 pm

1 stop3h 17m

Toronto Pearson Intl

Wed 7/1

6:05 am-9:14 am

1 stop4h 09m

$352

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/15

1:00 pm-5:23 pm

1 stop3h 23m

Toronto Pearson Intl

Thu 9/17

6:00 am-12:30 pm

1 stop7h 30m

$353

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 6/4

9:22 am-5:21 pm

1 stop6h 59m

Toronto Pearson Intl

Mon 6/8

6:05 am-9:14 am

1 stop4h 09m

$360

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 6/4

9:22 am-5:21 pm

1 stop6h 59m

Toronto Pearson Intl

Mon 6/8

6:05 am-9:14 am

1 stop4h 09m

$362

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/28

9:22 am-5:21 pm

1 stop6h 59m

Toronto Pearson Intl

Sun 5/31

12:09 pm-6:33 pm

1 stop7h 24m

$363

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 6/9

9:22 am-5:29 pm

1 stop7h 07m

Toronto Pearson Intl

Tue 6/16

2:34 pm-6:36 pm

1 stop5h 02m

$364

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Chicago Midway Airport and Toronto Pearson Intl Airport?

What is the cheapest month to fly to Toronto Pearson Intl Airport?

The cheapest month to fly to Toronto Pearson Intl Airport from Chicago Midway Airport is in July. Flight prices, which tend to average around $211, are often lower during this time because this is during the off-season. If you don’t want to visit Toronto Pearson Intl Airport in July, then you should wait until November to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $224.

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 $435. The most expensive day to fly to Toronto Pearson Intl Airport is Sunday, with ticket prices averaging around $732.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $411 when looking at flights departing in the evening. Flights in the afternoon are often more expensive with an average ticket price of $750.

Can stopping save me money on Chicago Midway Airport to Toronto Pearson Intl Airport flights?

You could potentially save up to 66% on your flight if you consider stops on a Chicago Midway Airport to Toronto Pearson Intl Airport flight.

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

Fastest flight time

3h 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 10m
There are no direct flights from Chicago Midway Airport to Toronto Pearson Intl Airport. There are no popular flight routes from Chicago Midway Airport to Toronto Pearson Intl Airport.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Toronto Pearson Intl Airport

  • 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 10m.

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

  • 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.

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

Best airlines flying from Chicago Midway Airport to Toronto Pearson Intl Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Toronto Pearson Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $88Free CancellationRating
7.9
8,450 reviews
Search Delta flights

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
Kitchener
Barrie
Richmond Hill
Oakville
Burlington
Collingwood
Cambridge
Peterborough
Guelph
Orillia
Whitby
Brantford
Oshawa
Stratford

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.

An easier way to manage your Toronto Pearson Intl Airport trip

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