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Cheap flights from Chicago Midway Airport to Toronto from $111

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 9/15. 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

Discover deals from 900+ travel sites with momondo.

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
5:03 pm - 10:59 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 56m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:08 pm - 6:33 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
$279Delta
Fri, Sep 11 - Fri, Sep 18
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$279Delta
Thu, Sep 10 - Fri, Sep 11
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$279Delta
Wed, Sep 23 - Wed, Sep 30
Delta Logo
5:37 pm - 10:59 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 22m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:08 pm - 6:33 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
$279Delta
Thu, Sep 10 - Thu, Sep 17
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:45 am - 12:39 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
3h 54m1 stop Detroit Metropolitan Wayne County
$279Delta
Mon, Sep 21 - Sat, Sep 26
Delta Logo
9:24 am - 5:24 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
7h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:08 pm - 4:57 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
5h 49m1 stop Detroit Metropolitan Wayne County
$279Delta
Mon, Sep 7 - Wed, Sep 9
Delta Logo
6:40 pm - 10:59 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 19m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$279Delta
Sun, Sep 13 - Sun, Sep 20
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$279Delta
Thu, Sep 10 - Tue, Sep 15
WestJet Logo
9:34 am - 5:25 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
WestJet Logo
12:13 pm - 6:38 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
$336WestJet
Tue, Sep 15 - Thu, Sep 17
KLM Logo
6:44 pm - 10:56 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 12m1 stop Detroit Metropolitan Wayne County
KLM Logo
9:40 am - 12:47 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$338KLM
Sat, Oct 31 - Tue, Nov 3

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KLM flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best KLM deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets
KLM
Sep 10
MDW5:37 pmChicago Midway
4h 22m
1 stop
YYZ10:59 pmToronto Pearson Intl
Sep 13
YYZ6:00 amToronto Pearson Intl
4h 07m
1 stop
MDW9:07 amChicago Midway
$390
KLM
Aug 21
MDW9:24 amChicago Midway
4h 56m
1 stop
YYZ3:20 pmToronto Pearson Intl
Aug 23
YYZ12:09 pmToronto Pearson Intl
7h 24m
1 stop
MDW6:33 pmChicago Midway
$593

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 15
MDW9:29 amChicago Midway
6h 51m
1 stop
YYZ5:20 pmToronto Pearson Intl
Sep 21
YYZ12:08 pmToronto Pearson Intl
7h 25m
1 stop
MDW6:33 pmChicago Midway
$279
Delta
Sep 11
MDW5:03 pmChicago Midway
4h 56m
1 stop
YYZ10:59 pmToronto Pearson Intl
Sep 16
YYZ12:08 pmToronto Pearson Intl
7h 25m
1 stop
MDW6:33 pmChicago Midway
$290
Delta
Sep 16
MDW9:29 amChicago Midway
6h 51m
1 stop
YYZ5:20 pmToronto Pearson Intl
Sep 23
YYZ4:05 pmToronto Pearson Intl
3h 28m
1 stop
MDW6:33 pmChicago Midway
$307

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 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

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Fri 9/11

5:03 pm-10:59 pm

1 stop4h 56m

Toronto Pearson Intl

Fri 9/18

12:08 pm-6:33 pm

1 stop7h 25m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 9/10

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Fri 9/11

6:00 am-9:07 am

1 stop4h 07m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 9/23

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Wed 9/30

6:00 am-9:07 am

1 stop4h 07m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 9/10

5:37 pm-10:59 pm

1 stop4h 22m

Toronto Pearson Intl

Thu 9/17

12:08 pm-6:33 pm

1 stop7h 25m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Mon 9/21

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Sat 9/26

9:45 am-12:39 pm

1 stop3h 54m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Mon 9/7

9:24 am-5:24 pm

1 stop7h 00m

Toronto Pearson Intl

Wed 9/9

12:08 pm-4:57 pm

1 stop5h 49m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sun 9/13

6:40 pm-10:59 pm

1 stop3h 19m

Toronto Pearson Intl

Sun 9/20

6:00 am-9:07 am

1 stop4h 07m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 9/10

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Tue 9/15

6:00 am-9:07 am

1 stop4h 07m

$279

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Tue 9/15

9:34 am-5:25 pm

1 stop6h 51m

Toronto Pearson Intl

Thu 9/17

12:13 pm-6:38 pm

1 stop7h 25m

$336
Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 10/31

6:44 pm-10:56 pm

1 stop3h 12m

Toronto Pearson Intl

Tue 11/3

9:40 am-12:47 pm

1 stop4h 07m

$338

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 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 $165, 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 December to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $232.

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 $434. The most expensive day to fly to Toronto Pearson Intl Airport is Monday, with ticket prices averaging around $665.

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 $444 when looking at flights departing in the evening. Flights in the afternoon are often more expensive with an average ticket price of $788.

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

You could potentially save up to 14% 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 03m

Direct flights

None
The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 03m
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 03m.

  • 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
7.8
8,502 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
Brampton
Niagara-on-the-Lake
Markham
Kitchener
Vaughan
Barrie
Collingwood
Burlington
Richmond Hill
Oakville
Orillia
Oshawa
Whitby
Peterborough
Cambridge
Guelph
Stratford
Milton

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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