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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 201

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 26/3. 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
6:30 a.m. - 1:05 p.m.
YYZ
-
MDW
7h 35m
1 stop
Delta Logo
9:34 a.m. - 4:10 p.m.
MDW
-
YYZ
5h 36m
1 stop
C$ 309Delta
Thu, 26 Feb - Sun, 1 Mar
Delta Logo
12:11 p.m. - 5:37 p.m.
YYZ
-
MDW
6h 26m
1 stop
Delta Logo
9:34 a.m. - 4:10 p.m.
MDW
-
YYZ
5h 36m
1 stop
C$ 320Delta
Fri, 27 Feb - Sun, 1 Mar
Delta Logo
2:14 p.m. - 6:14 p.m.
YYZ
-
MDW
5h 00m
1 stop
Delta Logo
9:22 a.m. - 1:24 p.m.
MDW
-
YYZ
3h 02m
1 stop
C$ 379Delta
Sat, 16 May - Mon, 18 May
WestJet Logo
12:11 p.m. - 5:37 p.m.
YYZ
-
MDW
6h 26m
1 stop
WestJet Logo
9:35 a.m. - 5:17 p.m.
MDW
-
YYZ
6h 42m
1 stop
C$ 384WestJet
Fri, 6 Mar - Fri, 13 Mar
Multiple Airlines Logo
7:10 a.m. - 2:26 p.m.
YYZ
-
MDW
8h 16m
1 stop
Multiple Airlines Logo
9:51 p.m. - 8:10 p.m.
MDW
-
YYZ
21h 19m
2 stops
C$ 390Multiple Airlines
Thu, 5 Mar - Mon, 9 Mar
Delta Logo
10:05 a.m. - 12:29 p.m.
YYZ
-
MDW
3h 24m
1 stop
Delta Logo
9:35 a.m. - 3:08 p.m.
MDW
-
YYZ
4h 33m
1 stop
C$ 394Delta
Sun, 8 Mar - Tue, 10 Mar
WestJet Logo
6:30 a.m. - 1:25 p.m.
YYZ
-
MDW
7h 55m
1 stop
WestJet Logo
9:30 a.m. - 11:06 p.m.
MDW
-
YYZ
12h 36m
1 stop
C$ 399WestJet
Thu, 2 Apr - Sun, 5 Apr
WestJet Logo
6:10 a.m. - 8:54 a.m.
YYZ
-
MDW
3h 44m
1 stop
WestJet Logo
9:35 a.m. - 3:08 p.m.
MDW
-
YYZ
4h 33m
1 stop
C$ 401WestJet
Fri, 6 Mar - Fri, 13 Mar
WestJet Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
WestJet Logo
9:35 a.m. - 3:08 p.m.
MDW
-
YYZ
4h 33m
1 stop
C$ 402WestJet
Wed, 11 Mar - Wed, 18 Mar
WestJet Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
WestJet Logo
9:30 a.m. - 3:18 p.m.
MDW
-
YYZ
4h 48m
1 stop
C$ 403WestJet
Mon, 9 Mar - Wed, 1 Jul

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
6 Mar
YYZ12:11 p.m.Toronto Pearson Intl
6h 26m
1 stop
MDW5:37 p.m.Chicago Midway
13 Mar
MDW9:35 a.m.Chicago Midway
6h 42m
1 stop
YYZ5:17 p.m.Toronto Pearson Intl
C$ 384
WestJet
2 Apr
YYZ6:30 a.m.Toronto Pearson Intl
7h 55m
1 stop
MDW1:25 p.m.Chicago Midway
5 Apr
MDW9:30 a.m.Chicago Midway
12h 36m
1 stop
YYZ11:06 p.m.Toronto Pearson Intl
C$ 399
WestJet
6 Mar
YYZ6:10 a.m.Toronto Pearson Intl
3h 44m
1 stop
MDW8:54 a.m.Chicago Midway
13 Mar
MDW9:35 a.m.Chicago Midway
4h 33m
1 stop
YYZ3:08 p.m.Toronto Pearson Intl
C$ 400

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
26 Feb
YYZ6:30 a.m.Toronto Pearson Intl
7h 35m
1 stop
MDW1:05 p.m.Chicago Midway
1 Mar
MDW9:34 a.m.Chicago Midway
5h 36m
1 stop
YYZ4:10 p.m.Toronto Pearson Intl
C$ 309
Delta
27 Feb
YYZ12:11 p.m.Toronto Pearson Intl
6h 26m
1 stop
MDW5:37 p.m.Chicago Midway
1 Mar
MDW9:34 a.m.Chicago Midway
5h 36m
1 stop
YYZ4:10 p.m.Toronto Pearson Intl
C$ 320
Delta
8 Mar
YYZ10:05 a.m.Toronto Pearson Intl
3h 24m
1 stop
MDW12:29 p.m.Chicago Midway
10 Mar
MDW9:35 a.m.Chicago Midway
4h 33m
1 stop
YYZ3:08 p.m.Toronto Pearson Intl
C$ 394

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 9 February 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

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop7h 35m

Chicago Midway

Sun 1/3

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

1 stop5h 36m

C$ 309

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 27/2

12:11 p.m.-5:37 p.m.

1 stop6h 26m

Chicago Midway

Sun 1/3

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

1 stop5h 36m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 16/5

2:14 p.m.-6:14 p.m.

1 stop5h 00m

Chicago Midway

Mon 18/5

9:22 a.m.-1:24 p.m.

1 stop3h 02m

C$ 379

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 6/3

12:11 p.m.-5:37 p.m.

1 stop6h 26m

Chicago Midway

Fri 13/3

9:35 a.m.-5:17 p.m.

1 stop6h 42m

C$ 384

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/3

7:10 a.m.-2:26 p.m.

1 stop8h 16m

Chicago Midway

Mon 9/3

9:51 p.m.-8:10 p.m.

2 stops21h 19m

C$ 390

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 8/3

10:05 a.m.-12:29 p.m.

1 stop3h 24m

Chicago Midway

Tue 10/3

9:35 a.m.-3:08 p.m.

1 stop4h 33m

C$ 394

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/4

6:30 a.m.-1:25 p.m.

1 stop7h 55m

Chicago Midway

Sun 5/4

9:30 a.m.-11:06 p.m.

1 stop12h 36m

C$ 399

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 6/3

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

1 stop3h 44m

Chicago Midway

Fri 13/3

9:35 a.m.-3:08 p.m.

1 stop4h 33m

C$ 400

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 11/3

12:15 p.m.-5:54 p.m.

1 stop6h 39m

Chicago Midway

Wed 18/3

9:35 a.m.-3:08 p.m.

1 stop4h 33m

C$ 402

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 9/3

12:15 p.m.-5:54 p.m.

1 stop6h 39m

Chicago Midway

Wed 1/7

9:30 a.m.-3:18 p.m.

1 stop4h 48m

C$ 403

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 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 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$ 267. 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$ 292.

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$ 279. 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 33m

Direct flights

None
The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 33m
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 33m, 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$ 112Free CancellationRating
7.9
414 reviews
Search Porter Airlines flights

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?

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

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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