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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 208

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 7/9. 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
1 adult, Economy, 0 bags

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
9:45 a.m. - 12:34 p.m.
YYZ
-
MDW
3h 49m
1 stop
Delta Logo
9:30 a.m. - 1:34 p.m.
MDW
-
YYZ
3h 04m
1 stop
C$ 335Delta
Fri, 25 Sep - Sun, 27 Sep
Delta Logo
12:09 p.m. - 4:59 p.m.
YYZ
-
MDW
5h 50m
1 stop
Delta Logo
5:59 p.m. - 10:57 p.m.
MDW
-
YYZ
3h 58m
1 stop
C$ 344Delta
Tue, 1 Sep - Sun, 13 Sep
Delta Logo
9:45 a.m. - 12:46 p.m.
YYZ
-
MDW
4h 01m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 352Delta
Tue, 30 Jun - Thu, 2 Jul
Multiple Airlines Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Multiple Airlines Logo
9:19 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 05m
1 stop
C$ 354Multiple Airlines
Thu, 2 Jul - Wed, 8 Jul
Delta Logo
6:10 a.m. - 12:39 p.m.
YYZ
-
MDW
7h 29m
1 stop
Delta Logo
5:45 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 14m
1 stop
C$ 376Delta
Mon, 7 Sep - Sat, 12 Sep
KLM Logo
12:09 p.m. - 6:25 p.m.
YYZ
-
MDW
7h 16m
1 stop
KLM Logo
9:19 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 05m
1 stop
C$ 377KLM
Sun, 26 Jul - Sun, 2 Aug
Delta Logo
9:45 a.m. - 12:46 p.m.
YYZ
-
MDW
4h 01m
1 stop
Delta Logo
9:17 a.m. - 3:19 p.m.
MDW
-
YYZ
5h 02m
1 stop
C$ 384Delta
Tue, 30 Jun - Fri, 3 Jul
Delta Logo
6:10 a.m. - 9:13 a.m.
YYZ
-
MDW
4h 03m
1 stop
Delta Logo
9:19 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 05m
1 stop
C$ 386Delta
Sun, 26 Jul - Sun, 2 Aug
Delta Logo
2:15 p.m. - 6:37 p.m.
YYZ
-
MDW
5h 22m
1 stop
Delta Logo
6:45 p.m. - 11:00 p.m.
MDW
-
YYZ
3h 15m
1 stop
C$ 387Delta
Sat, 24 Oct - Tue, 27 Oct
Delta Logo
12:15 p.m. - 6:37 p.m.
YYZ
-
MDW
7h 22m
1 stop
Delta Logo
1:00 p.m. - 5:22 p.m.
MDW
-
YYZ
3h 22m
1 stop
C$ 389Delta
Sun, 25 Oct - Fri, 30 Oct

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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
11 Sep
YYZ12:08 p.m.Toronto Pearson Intl
5h 49m
1 stop
MDW4:57 p.m.Chicago Midway
14 Sep
MDW9:30 a.m.Chicago Midway
6h 50m
1 stop
YYZ5:20 p.m.Toronto Pearson Intl
C$ 335
Delta
1 Sep
YYZ12:09 p.m.Toronto Pearson Intl
5h 50m
1 stop
MDW4:59 p.m.Chicago Midway
13 Sep
MDW5:59 p.m.Chicago Midway
3h 58m
1 stop
YYZ10:57 p.m.Toronto Pearson Intl
C$ 344
Delta
30 Jun
YYZ9:45 a.m.Toronto Pearson Intl
4h 01m
1 stop
MDW12:46 p.m.Chicago Midway
2 Jul
MDW1:26 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:02 p.m.Toronto Pearson Intl
C$ 352

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
27 Jul
YYZ12:14 p.m.Toronto Pearson Intl
7h 16m
1 stop
MDW6:30 p.m.Chicago Midway
3 Aug
MDW1:32 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:08 p.m.Toronto Pearson Intl
C$ 503
WestJet
29 Jun
YYZ6:10 a.m.Toronto Pearson Intl
7h 41m
1 stop
MDW12:51 p.m.Chicago Midway
6 Jul
MDW1:31 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:07 p.m.Toronto Pearson Intl
C$ 527
WestJet
19 Jun
YYZ6:10 a.m.Toronto Pearson Intl
7h 41m
1 stop
MDW12:51 p.m.Chicago Midway
21 Jun
MDW1:31 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:07 p.m.Toronto Pearson Intl
C$ 637

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 16 June 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
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 25/9

9:45 a.m.-12:34 p.m.

1 stop3h 49m

Chicago Midway

Sun 27/9

9:30 a.m.-1:34 p.m.

1 stop3h 04m

C$ 335

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 1/9

12:09 p.m.-4:59 p.m.

1 stop5h 50m

Chicago Midway

Sun 13/9

5:59 p.m.-10:57 p.m.

1 stop3h 58m

C$ 344

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 30/6

9:45 a.m.-12:46 p.m.

1 stop4h 01m

Chicago Midway

Thu 2/7

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 352

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/7

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Wed 8/7

9:19 a.m.-5:24 p.m.

1 stop7h 05m

C$ 354

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 7/9

6:10 a.m.-12:39 p.m.

1 stop7h 29m

Chicago Midway

Sat 12/9

5:45 p.m.-10:59 p.m.

1 stop4h 14m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 26/7

12:09 p.m.-6:25 p.m.

1 stop7h 16m

Chicago Midway

Sun 2/8

9:19 a.m.-5:24 p.m.

1 stop7h 05m

C$ 377

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 30/6

9:45 a.m.-12:46 p.m.

1 stop4h 01m

Chicago Midway

Fri 3/7

9:17 a.m.-3:19 p.m.

1 stop5h 02m

C$ 384

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 26/7

6:10 a.m.-9:13 a.m.

1 stop4h 03m

Chicago Midway

Sun 2/8

9:19 a.m.-5:24 p.m.

1 stop7h 05m

C$ 386

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 24/10

2:15 p.m.-6:37 p.m.

1 stop5h 22m

Chicago Midway

Tue 27/10

6:45 p.m.-11:00 p.m.

1 stop3h 15m

C$ 387

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 25/10

12:15 p.m.-6:37 p.m.

1 stop7h 22m

Chicago Midway

Fri 30/10

1:00 p.m.-5:22 p.m.

1 stop3h 22m

C$ 389

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, March 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$ 0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Toronto Pearson Intl Airport during the month January is also very affordable. Most momondo users find prices during this month for around C$ 0.

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$ 300. 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$ 326.

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$ 313. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 677.

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$ 115Free CancellationRating
8.0
438 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

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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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