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Cheap flights from Toronto to Chicago from C$ 160

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 18/1. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 252Porter Airlines
Thu, 15 Jan - Sun, 18 Jan
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$ 255Porter Airlines
Fri, 16 Jan - Fri, 23 Jan
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 256Porter Airlines
Sun, 25 Jan - Mon, 26 Jan
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 258Porter Airlines
Fri, 16 Jan - Fri, 23 Jan
Porter Airlines Logo
11:00 a.m. - 11:50 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 259Porter Airlines
Sat, 24 Jan - Thu, 29 Jan
Porter Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 263Porter Airlines
Thu, 15 Jan - Thu, 29 Jan
Delta Logo
10:05 a.m. - 12:46 p.m.
YYZ
-
MDW
3h 41m1 stop
Delta Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
C$ 292Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m1 stop
C$ 293Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
Delta Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
C$ 303Delta
Thu, 5 Feb - Sun, 8 Feb
WestJet Logo
10:05 a.m. - 12:48 p.m.
YYZ
-
MDW
3h 43m1 stop
WestJet Logo
6:14 p.m. - 10:41 p.m.
MDW
-
YYZ
3h 27m1 stop
C$ 360WestJet
Wed, 14 Jan - Sun, 18 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
15 Jan
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
18 Jan
MDW4:15 p.m.Chicago Midway
1h 42m
YTZ6:57 p.m.Toronto Island
C$ 252
Find similar
Porter Airlines
16 Jan
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
23 Jan
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 255
Find similar
Porter Airlines
25 Jan
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
26 Jan
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 256
Find similar

WestJet flights from Toronto to Chicago Midway Airport

Our best WestJet deals on Toronto to Chicago Midway Airport flight tickets
WestJet
14 Jan
YYZ10:05 a.m.Toronto Pearson Intl
3h 43m
1 stop
MDW12:48 p.m.Chicago Midway
18 Jan
MDW6:14 p.m.Chicago Midway
3h 27m
1 stop
YYZ10:41 p.m.Toronto Pearson Intl
C$ 360
Find similar
WestJet
16 Jan
YYZ12:10 p.m.Toronto Pearson Intl
6h 27m
1 stop
MDW5:37 p.m.Chicago Midway
18 Jan
MDW9:32 a.m.Chicago Midway
5h 40m
1 stop
YYZ4:12 p.m.Toronto Pearson Intl
C$ 362
Find similar
WestJet
8 Jan
YYZ7:45 a.m.Toronto Pearson Intl
6h 03m
1 stop
MDW12:48 p.m.Chicago Midway
12 Jan
MDW6:14 p.m.Chicago Midway
3h 27m
1 stop
YYZ10:41 p.m.Toronto Pearson Intl
C$ 366
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 18 December 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

Thu 15/1

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

Nonstop1h 50m

Chicago Midway

Sun 18/1

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

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 16/1

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

Nonstop1h 50m

Chicago Midway

Fri 23/1

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

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

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

Nonstop1h 50m

Chicago Midway

Mon 26/1

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 16/1

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

Nonstop1h 50m

Chicago Midway

Fri 23/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 24/1

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Thu 29/1

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

Nonstop1h 42m

C$ 259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/1

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Thu 29/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 263

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

10:05 a.m.-12:46 p.m.

1 stop3h 41m

Chicago Midway

Sun 8/2

9:33 a.m.-4:12 p.m.

1 stop5h 39m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

6:00 a.m.-8:52 a.m.

1 stop3h 52m

Chicago Midway

Sun 8/2

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 293

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

6:00 a.m.-8:52 a.m.

1 stop3h 52m

Chicago Midway

Sun 8/2

9:33 a.m.-4:12 p.m.

1 stop5h 39m

C$ 303

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 14/1

10:05 a.m.-12:48 p.m.

1 stop3h 43m

Chicago Midway

Sun 18/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 360

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 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 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$ 237. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Toronto during the month October is also very affordable. Most momondo users find prices during this month for around C$ 277.

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 Monday when prices can be found for as low as C$ 279. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday 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$ 304.

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$ 292. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 668.

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$ 152

Fastest flight time

1h 49m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is C$ 152. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is C$ 245.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 49m
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 49m.

  • 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$ 195Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Toronto to Chicago Midway Airport

    Porter Airlines flight deals from Toronto to Chicago Midway Airport start from C$ 195 round-trip. Over the 12 Porter Airlines flights for this route in a normal week, average airfare is usually C$ 330 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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