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Cheap flights from Toronto to Chicago from C$ 183

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 25/11. 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
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 258Porter Airlines
Find Deal
Sun, 23 Nov - Mon, 8 Dec
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 259Multiple Airlines
Find Deal
Sun, 1 Mar - Sun, 15 Mar
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 261Porter Airlines
Find Deal
Mon, 24 Nov - Mon, 8 Dec
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 281Air Transat
Find Deal
Mon, 17 Nov - Wed, 19 Nov
KLM Logo
3:38 p.m. - 6:14 p.m.YYZ-MDW
3h 36m1 stop
KLM Logo
6:48 p.m. - 11:05 p.m.MDW-YYZ
3h 17m1 stop
C$ 287KLM
Find Deal
Fri, 21 Nov - Mon, 24 Nov
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
12:45 p.m. - 3:27 p.m.MDW-YTZ
1h 42mdirect
C$ 291Air Transat
Find Deal
Thu, 19 Mar - Sat, 21 Mar
Delta Logo
12:13 p.m. - 6:00 p.m.YYZ-MDW
6h 47m1 stop
Delta Logo
1:14 p.m. - 5:15 p.m.MDW-YYZ
3h 01m1 stop
C$ 294Delta
Find Deal
Tue, 2 Dec - Tue, 9 Dec
Delta Logo
6:05 a.m. - 8:54 a.m.YYZ-MDW
3h 49m1 stop
Delta Logo
9:59 a.m. - 4:15 p.m.MDW-YYZ
5h 16m1 stop
C$ 295Delta
Find Deal
Sun, 23 Nov - Sat, 13 Dec
WestJet Logo
6:30 a.m. - 1:10 p.m.YYZ-MDW
7h 40m1 stop
WestJet Logo
9:59 a.m. - 4:15 p.m.MDW-YYZ
5h 16m1 stop
C$ 369WestJet
Find Deal
Thu, 18 Dec - Fri, 19 Dec
WestJet Logo
6:10 a.m. - 10:34 a.m.YYZ-MDW
5h 24m1 stop
WestJet Logo
9:50 a.m. - 3:59 p.m.MDW-YYZ
5h 09m1 stop
C$ 373WestJet
Find Deal
Sun, 11 Jan - Thu, 15 Jan

Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Porter Airlines
23 Nov
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
8 Dec
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 258
Find similar
Porter Airlines
24 Nov
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
8 Dec
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 261
Find similar
Porter Airlines
17 Nov
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
21 Nov
MDW4:15 p.m.Chicago Midway
1h 42m
YTZ6:57 p.m.Toronto Island
C$ 262
Find similar

Air Transat flights from Toronto to Chicago Midway Airport

Our best Air Transat deals on Toronto to Chicago Midway Airport flight tickets
Air Transat
17 Nov
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
19 Nov
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 281
Find similar
Air Transat
19 Mar
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
21 Mar
MDW12:45 p.m.Chicago Midway
1h 42m
YTZ3:27 p.m.Toronto Island
C$ 291
Find similar
Air Transat
5 Dec
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
8 Dec
MDW4:15 p.m.Chicago Midway
1h 42m
YTZ6:57 p.m.Toronto Island
C$ 293
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto to Chicago Midway 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 96,600 searches. Data last updated 30 October 2025.
Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 23/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/3

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

Nonstop1h 50m

Chicago Midway

Sun 15/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/11

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

Nonstop1h 50m

Chicago Midway

Wed 19/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 281

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 21/11

3:38 p.m.-6:14 p.m.

1 stop3h 36m

Chicago Midway

Mon 24/11

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 287

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/3

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

Nonstop1h 50m

Chicago Midway

Sat 21/3

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

Nonstop1h 42m

C$ 291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 2/12

12:13 p.m.-6:00 p.m.

1 stop6h 47m

Chicago Midway

Tue 9/12

1:14 p.m.-5:15 p.m.

1 stop3h 01m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 23/11

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Sat 13/12

9:59 a.m.-4:15 p.m.

1 stop5h 16m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 18/12

6:30 a.m.-1:10 p.m.

1 stop7h 40m

Chicago Midway

Fri 19/12

9:59 a.m.-4:15 p.m.

1 stop5h 16m

C$ 369

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:10 a.m.-10:34 a.m.

1 stop5h 24m

Chicago Midway

Thu 15/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 373

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto to Chicago Midway 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 Toronto and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

In general, September is the cheapest month to fly from Toronto to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 240. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Toronto during the month May is also very affordable. Most momondo users find prices during this month for around C$ 287.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Friday when prices can be found for as low as C$ 303. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 328.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Toronto to Chicago Midway Airport during this time can be as low as C$ 311. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 675.

What is the cheapest Toronto to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago Midway flight prices

What cabin class options are available on Toronto to Chicago Midway flights?

There is only 1 cabin class available to choose from on Toronto to Chicago Midway 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 Toronto to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago Midway Airport.

How have Toronto to Chicago Midway Airport flight prices changed over time?

When to book flights from Toronto to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto to Chicago Midway Airport (YTO to MDW) flight deals and tips

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

Best price found

C$ 196

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is C$ 196. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is C$ 347.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 50m
Direct flights go from Toronto to Chicago Midway Airport every day.
Search flight deals

  • How far is Toronto to Chicago Midway by plane?

    There are 713.1 km between Toronto and Chicago Midway. By plane, this route typically takes 1h 50m.

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

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

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

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

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Toronto to Chicago Midway Airport?

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

Best airlines flying from Toronto to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 197Free CancellationRating
8.0
384 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 553Free CancellationRating
7.2
3,152 reviews
Search WestJet flights

  • Porter Airlines Flights From Toronto to Chicago Midway Airport

    Porter Airlines flight deals from Toronto to Chicago Midway Airport start from C$ 197 round-trip. Over the 6 Porter Airlines flights for this route in a normal week, average airfare is usually C$ 321 round-trip - but some users have found much cheaper deals with momondo.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Chicago for you.

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

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

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

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

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

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

An easier way to manage your Chicago Midway Airport trip

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