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Cheap flights from Chicago Midway Airport to Toronto from C$ 104

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 30/9. 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

Cheap round-trip flights

Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 237Porter Airlines
Find Deal
Thu, 2 Oct - Sun, 5 Oct
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 238Porter Airlines
Find Deal
Tue, 30 Sep - Sun, 5 Oct
Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 276
Find Deal
Sat, 4 Oct - Sun, 5 Oct
Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 278
Find Deal
Tue, 7 Oct - Wed, 8 Oct
Air Transat Logo
12:45 p.m. - 3:27 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 310Air Transat
Find Deal
Sat, 22 Nov - Tue, 25 Nov
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
C$ 312Air Transat
Find Deal
Wed, 8 Oct - Wed, 15 Oct
Delta Logo
9:35 a.m. - 5:23 p.m.MDW-YYZ
6h 48m1 stop
Delta Logo
12:15 p.m. - 6:35 p.m.YYZ-MDW
7h 20m1 stop
C$ 338Delta
Find Deal
Thu, 2 Oct - Sun, 5 Oct
Delta Logo
6:15 p.m. - 10:56 p.m.MDW-YYZ
3h 41m1 stop
Delta Logo
12:15 p.m. - 6:25 p.m.YYZ-MDW
7h 10m1 stop
C$ 384Delta
Find Deal
Fri, 3 Oct - Mon, 6 Oct
WestJet Logo
10:35 a.m. - 4:50 p.m.MDW-YYZ
5h 15m1 stop
WestJet Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
C$ 396WestJet
Find Deal
Sat, 18 Oct - Sun, 19 Oct
WestJet Logo
10:47 a.m. - 9:59 p.m.MDW-YYZ
10h 12m1 stop
WestJet Logo
12:25 p.m. - 9:52 a.m.YYZ-MDW
22h 27m1 stop
C$ 407WestJet
Find Deal
Wed, 19 Nov - Sun, 23 Nov

WestJet flights from Chicago Midway Airport to Toronto

Our best WestJet deals on Chicago Midway Airport to Toronto flight tickets
WestJet
18 Oct
MDW10:35 a.m.Chicago Midway
5h 15m
1 stop
YYZ4:50 p.m.Toronto Pearson Intl
19 Oct
YYZ6:00 p.m.Toronto Pearson Intl
5h 14m
1 stop
MDW10:14 p.m.Chicago Midway
C$ 396
Find similar
WestJet
19 Nov
MDW10:47 a.m.Chicago Midway
10h 12m
1 stop
YYZ9:59 p.m.Toronto Pearson Intl
23 Nov
YYZ12:25 p.m.Toronto Pearson Intl
22h 27m
1 stop
MDW9:52 a.m.Chicago Midway
C$ 407
Find similar
WestJet
18 Nov
MDW10:47 a.m.Chicago Midway
5h 13m
1 stop
YYZ5:00 p.m.Toronto Pearson Intl
22 Nov
YYZ6:30 p.m.Toronto Pearson Intl
16h 22m
2 stops
MDW9:52 a.m.Chicago Midway
C$ 409
Find similar

Delta flights from Chicago Midway Airport to Toronto

Our best Delta deals on Chicago Midway Airport to Toronto flight tickets
Delta
2 Oct
MDW9:35 a.m.Chicago Midway
6h 48m
1 stop
YYZ5:23 p.m.Toronto Pearson Intl
5 Oct
YYZ12:15 p.m.Toronto Pearson Intl
7h 20m
1 stop
MDW6:35 p.m.Chicago Midway
C$ 338
Find similar
Delta
3 Oct
MDW6:15 p.m.Chicago Midway
3h 41m
1 stop
YYZ10:56 p.m.Toronto Pearson Intl
6 Oct
YYZ12:15 p.m.Toronto Pearson Intl
7h 10m
1 stop
MDW6:25 p.m.Chicago Midway
C$ 384
Find similar
Delta
9 Oct
MDW9:35 a.m.Chicago Midway
6h 44m
1 stop
YYZ5:19 p.m.Toronto Pearson Intl
16 Oct
YYZ6:15 a.m.Toronto Pearson Intl
7h 13m
1 stop
MDW12:28 p.m.Chicago Midway
C$ 420
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 96,600 searches. Data last updated 11 September 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

Thu 2/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 237

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 30/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 238

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 7/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Wed 8/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 278

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 22/11

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

Toronto Island

Tue 25/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 310

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 8/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Wed 15/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 312

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/10

9:35 a.m.-5:23 p.m.

1 stop6h 48m

Toronto Pearson Intl

Sun 5/10

12:15 p.m.-6:35 p.m.

1 stop7h 20m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 3/10

6:15 p.m.-10:56 p.m.

1 stop3h 41m

Toronto Pearson Intl

Mon 6/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

C$ 384

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 18/10

10:35 a.m.-4:50 p.m.

1 stop5h 15m

Toronto Pearson Intl

Sun 19/10

6:00 p.m.-10:14 p.m.

1 stop5h 14m

C$ 396

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 19/11

10:47 a.m.-9:59 p.m.

1 stop10h 12m

Toronto Pearson Intl

Sun 23/11

12:25 p.m.-9:52 a.m.

1 stop22h 27m

C$ 407

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 C$ 248. The month of August is another great option to travel to Toronto, with average flight prices from Chicago Midway Airport averaging around C$ 283.

What is the cheapest day to depart on your flight to Toronto?

According to our data, Saturday is the cheapest day to fly to Toronto from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was C$ 373. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from Chicago Midway Airport to Toronto on a Monday will generally be more expensive and average around C$ 467. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Flying to Toronto from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as C$ 317 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around C$ 457. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 is only 1 cabin class 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 September 2025, prices for Chicago Midway Airport to Toronto flights are approximately 74% cheaper 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

C$ 125

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 C$ 125. The best round-trip flight deal from Chicago Midway Airport to Toronto found on momondo in the last 72 hours is C$ 266.
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?

    A flight from Chicago Midway to Toronto will travel around 713.1 km. Flights usually cover this in 1h 42m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago Midway Airport to Toronto were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Toronto?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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?

Travelling to a place near Toronto?

Book flights to Toronto if you plan to visit one of these locations
Apsley

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Toronto . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Toronto with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Toronto from Chicago with this policy.

How can momondo help me find flights from Chicago to Toronto?

momondo provides multiple filters to help you find the best flight to Toronto from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Toronto right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Toronto flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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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 83.6 km from Toronto
Toronto Region of Waterloo Intl Airport
Toronto Island Airport
Toronto Pearson Intl Airport