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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 185

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 Pearson Intl Airport to Chicago departing on 9/2. 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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Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
Delta Logo
6:35 p.m. - 10:42 p.m.
MDW
-
YYZ
3h 07m1 stop
C$ 279Delta
Tue, 3 Feb - Tue, 10 Feb
Delta Logo
7:45 a.m. - 12:46 p.m.
YYZ
-
MDW
6h 01m1 stop
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m1 stop
C$ 292Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
10:05 a.m. - 12:46 p.m.
YYZ
-
MDW
3h 41m1 stop
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m1 stop
C$ 294Delta
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. - 10:42 p.m.
MDW
-
YYZ
8h 16m1 stop
C$ 316Delta
Sun, 25 Jan - Sun, 1 Feb
Delta Logo
10:05 a.m. - 12:48 p.m.
YYZ
-
MDW
3h 43m1 stop
Delta Logo
1:28 p.m. - 10:41 p.m.
MDW
-
YYZ
8h 13m1 stop
C$ 339Delta
Wed, 14 Jan - Sun, 18 Jan
Multiple Airlines Logo
7:45 a.m. - 12:46 p.m.
YYZ
-
MDW
6h 01m1 stop
Multiple Airlines Logo
9:22 p.m. - 2:20 p.m.
MDW
-
YYZ
15h 58m1 stop
C$ 346Multiple Airlines
Sat, 21 Feb - Mon, 23 Feb
Delta Logo
12:28 p.m. - 6:45 p.m.
YYZ
-
MDW
7h 17m1 stop
Delta Logo
9:27 a.m. - 5:20 p.m.
MDW
-
YYZ
6h 53m1 stop
C$ 369Delta
Thu, 23 Apr - Mon, 4 May
Delta Logo
10:05 a.m. - 5:37 p.m.
YYZ
-
MDW
8h 32m1 stop
Delta Logo
9:34 a.m. - 4:10 p.m.
MDW
-
YYZ
5h 36m1 stop
C$ 372Delta
Fri, 13 Feb - Mon, 16 Feb
WestJet Logo
12:21 p.m. - 5:29 p.m.
YYZ
-
MDW
6h 08m1 stop
WestJet Logo
10:48 a.m. - 5:04 p.m.
MDW
-
YYZ
5h 16m1 stop
C$ 376WestJet
Fri, 23 Jan - Fri, 30 Jan
WestJet Logo
6:10 a.m. - 8:54 a.m.
YYZ
-
MDW
3h 44m1 stop
WestJet Logo
9:34 a.m. - 4:10 p.m.
MDW
-
YYZ
5h 36m1 stop
C$ 377WestJet
Thu, 26 Feb - Mon, 2 Mar

WestJet flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Our best WestJet deals on Toronto Pearson Intl Airport to Chicago Midway Airport flight tickets
WestJet
23 Jan
YYZ12:21 p.m.Toronto Pearson Intl
6h 08m
1 stop
MDW5:29 p.m.Chicago Midway
30 Jan
MDW10:48 a.m.Chicago Midway
5h 16m
1 stop
YYZ5:04 p.m.Toronto Pearson Intl
C$ 376
Find similar
WestJet
26 Feb
YYZ6:10 a.m.Toronto Pearson Intl
3h 44m
1 stop
MDW8:54 a.m.Chicago Midway
2 Mar
MDW9:34 a.m.Chicago Midway
5h 36m
1 stop
YYZ4:10 p.m.Toronto Pearson Intl
C$ 377
Find similar
WestJet
18 Mar
YYZ10:05 a.m.Toronto Pearson Intl
3h 24m
1 stop
MDW12:29 p.m.Chicago Midway
22 Mar
MDW7:20 p.m.Chicago Midway
19h 39m
1 stop
YYZ3:59 p.m.Toronto Pearson Intl
C$ 379
Find similar

Delta flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Our best Delta deals on Toronto Pearson Intl Airport to Chicago Midway Airport flight tickets
Delta
5 Feb
YYZ7:45 a.m.Toronto Pearson Intl
6h 01m
1 stop
MDW12:46 p.m.Chicago Midway
8 Feb
MDW1:26 p.m.Chicago Midway
4h 42m
1 stop
YYZ7:08 p.m.Toronto Pearson Intl
C$ 292
Find similar
Delta
5 Feb
YYZ10:05 a.m.Toronto Pearson Intl
3h 41m
1 stop
MDW12:46 p.m.Chicago Midway
8 Feb
MDW1:26 p.m.Chicago Midway
4h 42m
1 stop
YYZ7:08 p.m.Toronto Pearson Intl
C$ 294
Find similar
Delta
25 Jan
YYZ6:00 a.m.Toronto Pearson Intl
3h 52m
1 stop
MDW8:52 a.m.Chicago Midway
1 Feb
MDW1:26 p.m.Chicago Midway
8h 16m
1 stop
YYZ10:42 p.m.Toronto Pearson Intl
C$ 316
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Pearson Intl Airport 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 28 December 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 3/2

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

1 stop3h 52m

Chicago Midway

Tue 10/2

6:35 p.m.-10:42 p.m.

1 stop3h 07m

C$ 279

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

Chicago Midway

Sun 8/2

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

1 stop4h 42m

C$ 292

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

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

1 stop4h 42m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 25/1

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

1 stop3h 52m

Chicago Midway

Sun 1/2

1:26 p.m.-10:42 p.m.

1 stop8h 16m

C$ 316

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

1:28 p.m.-10:41 p.m.

1 stop8h 13m

C$ 339

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 21/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

Chicago Midway

Mon 23/2

9:22 p.m.-2:20 p.m.

1 stop15h 58m

C$ 346

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 23/4

12:28 p.m.-6:45 p.m.

1 stop7h 17m

Chicago Midway

Mon 4/5

9:27 a.m.-5:20 p.m.

1 stop6h 53m

C$ 369

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 13/2

10:05 a.m.-5:37 p.m.

1 stop8h 32m

Chicago Midway

Mon 16/2

9:34 a.m.-4:10 p.m.

1 stop5h 36m

C$ 372

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 23/1

12:21 p.m.-5:29 p.m.

1 stop6h 08m

Chicago Midway

Fri 30/1

10:48 a.m.-5:04 p.m.

1 stop5h 16m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 26/2

6:10 a.m.-8:54 a.m.

1 stop3h 44m

Chicago Midway

Mon 2/3

9:34 a.m.-4:10 p.m.

1 stop5h 36m

C$ 377

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 Pearson Intl Airport 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 Pearson Intl Airport and Chicago Midway Airport?

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

In general, December is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 292. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Toronto Pearson Intl Airport during the month November is also very affordable. Most momondo users find prices during this month for around C$ 297.

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$ 269. 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 Pearson Intl Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 302.

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 Pearson Intl Airport to Chicago Midway Airport during this time can be as low as C$ 288. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 662.

When to book flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Pearson Intl Airport 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 Pearson Intl Airport to Chicago Midway Airport (YYZ to MDW) flight deals and tips

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

Fastest flight time

3h 37m

Direct flights

None
The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 37m
There are no direct flights from Toronto Pearson Intl Airport to Chicago Midway Airport. There are no popular flight routes from Toronto Pearson Intl Airport to Chicago Midway Airport.
Search flight deals

  • How far is Toronto Pearson Intl to Chicago Midway by plane?

    The straight-line distance from Toronto Pearson Intl to Chicago Midway is 695.6 km. Flights usually cover this in 3h 37m, depending on flying conditions and air traffic around both airports.

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

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

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

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

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 225Free CancellationRating
8.0
402 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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Hammond
Merrillville

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

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

Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.

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

Once all potential Toronto to Chicago 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 Toronto to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.

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