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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 205

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 8/5. 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

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
12:16 p.m. - 5:58 p.m.
YYZ
-
MDW
6h 42m
1 stop
Delta Logo
9:22 a.m. - 1:30 p.m.
MDW
-
YYZ
3h 08m
1 stop
C$ 316Delta
Tue, 5 May - Sat, 9 May
Delta Logo
12:29 p.m. - 5:56 p.m.
YYZ
-
MDW
6h 27m
1 stop
Delta Logo
9:22 a.m. - 1:30 p.m.
MDW
-
YYZ
3h 08m
1 stop
C$ 329Delta
Thu, 7 May - Sat, 9 May
Delta Logo
12:09 p.m. - 6:33 p.m.
YYZ
-
MDW
7h 24m
1 stop
Delta Logo
9:22 a.m. - 5:21 p.m.
MDW
-
YYZ
6h 59m
1 stop
C$ 330Delta
Fri, 8 May - Mon, 11 May
Delta Logo
6:10 a.m. - 8:43 a.m.
YYZ
-
MDW
3h 33m
1 stop
Delta Logo
9:22 a.m. - 1:30 p.m.
MDW
-
YYZ
3h 08m
1 stop
C$ 332Delta
Thu, 7 May - Sun, 10 May
WestJet Logo
12:14 p.m. - 6:36 p.m.
YYZ
-
MDW
7h 22m
1 stop
WestJet Logo
1:54 p.m. - 11:19 p.m.
MDW
-
YYZ
8h 25m
1 stop
C$ 349WestJet
Fri, 19 Jun - Mon, 22 Jun
Delta Logo
12:09 p.m. - 6:31 p.m.
YYZ
-
MDW
7h 22m
1 stop
Delta Logo
2:00 p.m. - 10:58 p.m.
MDW
-
YYZ
7h 58m
1 stop
C$ 355Delta
Thu, 2 Jul - Tue, 1 Sep
Delta Logo
12:09 p.m. - 6:33 p.m.
YYZ
-
MDW
7h 24m
1 stop
Delta Logo
9:22 a.m. - 5:21 p.m.
MDW
-
YYZ
6h 59m
1 stop
C$ 360Delta
Wed, 13 May - Sun, 17 May
Delta Logo
6:10 a.m. - 8:43 a.m.
YYZ
-
MDW
3h 33m
1 stop
Delta Logo
9:22 a.m. - 1:30 p.m.
MDW
-
YYZ
3h 08m
1 stop
C$ 362Delta
Sat, 9 May - Sun, 10 May
Delta Logo
2:20 p.m. - 6:33 p.m.
YYZ
-
MDW
5h 13m
1 stop
Delta Logo
9:17 a.m. - 1:39 p.m.
MDW
-
YYZ
3h 22m
1 stop
C$ 370Delta
Thu, 4 Jun - Tue, 9 Jun
Delta Logo
12:09 p.m. - 6:31 p.m.
YYZ
-
MDW
7h 22m
1 stop
Delta Logo
6:35 p.m. - 11:02 p.m.
MDW
-
YYZ
3h 27m
1 stop
C$ 371Delta
Mon, 15 Jun - Sat, 20 Jun

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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
19 Jun
YYZ12:14 p.m.Toronto Pearson Intl
7h 22m
1 stop
MDW6:36 p.m.Chicago Midway
22 Jun
MDW1:54 p.m.Chicago Midway
8h 25m
1 stop
YYZ11:19 p.m.Toronto Pearson Intl
C$ 349
WestJet
20 Jun
YYZ12:14 p.m.Toronto Pearson Intl
6h 57m
1 stop
MDW6:11 p.m.Chicago Midway
27 Jun
MDW9:22 a.m.Chicago Midway
7h 07m
1 stop
YYZ5:29 p.m.Toronto Pearson Intl
C$ 374
WestJet
16 Jun
YYZ2:34 p.m.Toronto Pearson Intl
5h 02m
1 stop
MDW6:36 p.m.Chicago Midway
21 Jun
MDW9:22 a.m.Chicago Midway
7h 07m
1 stop
YYZ5:29 p.m.Toronto Pearson Intl
C$ 411

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 May
YYZ12:16 p.m.Toronto Pearson Intl
6h 42m
1 stop
MDW5:58 p.m.Chicago Midway
9 May
MDW9:22 a.m.Chicago Midway
3h 08m
1 stop
YYZ1:30 p.m.Toronto Pearson Intl
C$ 316
Delta
7 May
YYZ12:29 p.m.Toronto Pearson Intl
6h 27m
1 stop
MDW5:56 p.m.Chicago Midway
9 May
MDW9:22 a.m.Chicago Midway
3h 08m
1 stop
YYZ1:30 p.m.Toronto Pearson Intl
C$ 329
Delta
8 May
YYZ12:09 p.m.Toronto Pearson Intl
7h 24m
1 stop
MDW6:33 p.m.Chicago Midway
11 May
MDW9:22 a.m.Chicago Midway
6h 59m
1 stop
YYZ5:21 p.m.Toronto Pearson Intl
C$ 330

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 15 April 2026.
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

Cheapest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 5/5

12:16 p.m.-5:58 p.m.

1 stop6h 42m

Chicago Midway

Sat 9/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

C$ 316

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 7/5

12:29 p.m.-5:56 p.m.

1 stop6h 27m

Chicago Midway

Sat 9/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 8/5

12:09 p.m.-6:33 p.m.

1 stop7h 24m

Chicago Midway

Mon 11/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 330
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 7/5

6:10 a.m.-8:43 a.m.

1 stop3h 33m

Chicago Midway

Sun 10/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

C$ 332

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 19/6

12:14 p.m.-6:36 p.m.

1 stop7h 22m

Chicago Midway

Mon 22/6

1:54 p.m.-11:19 p.m.

1 stop8h 25m

C$ 349

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/7

12:09 p.m.-6:31 p.m.

1 stop7h 22m

Chicago Midway

Tue 1/9

2:00 p.m.-10:58 p.m.

1 stop7h 58m

C$ 355

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 13/5

12:09 p.m.-6:33 p.m.

1 stop7h 24m

Chicago Midway

Sun 17/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 360

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 9/5

6:10 a.m.-8:43 a.m.

1 stop3h 33m

Chicago Midway

Sun 10/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

C$ 362

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/6

2:20 p.m.-6:33 p.m.

1 stop5h 13m

Chicago Midway

Tue 9/6

9:17 a.m.-1:39 p.m.

1 stop3h 22m

C$ 370

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 15/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

Chicago Midway

Sat 20/6

6:35 p.m.-11:02 p.m.

1 stop3h 27m

C$ 371

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 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$ 259. 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 Pearson Intl Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 313.

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 afternoon. Flights from Toronto Pearson Intl Airport to Chicago Midway Airport during this time can be as low as C$ 282. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 667.

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 15m

Direct flights

None
The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 15m
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

Frequently asked questions about flying from Toronto Pearson Intl Airport to Chicago Midway Airport

  • 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 15m, 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$ 113Free CancellationRating
8.0
435 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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

Why use momondo?

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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