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Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 200

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 29/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

Multiple Airlines Logo
12:50 p.m. - 10:20 p.m.YYZ-MDW
10h 30m1 stop
Multiple Airlines Logo
8:00 a.m. - 8:00 p.m.MDW-YYZ
11h 00m1 stop
C$ 305Multiple Airlines
Find Deal
Fri, 7 Nov - Mon, 10 Nov
WestJet Logo
6:20 a.m. - 10:30 a.m.YYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 a.m. - 4:50 p.m.MDW-YYZ
5h 15m1 stop
C$ 326WestJet
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Multiple Airlines Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
C$ 350Multiple Airlines
Find Deal
Thu, 16 Oct - Fri, 31 Oct
Multiple Airlines Logo
5:15 p.m. - 8:32 a.m.YYZ-MDW
16h 17m1 stop
Multiple Airlines Logo
9:32 a.m. - 2:05 p.m.MDW-YYZ
27h 33m1 stop
C$ 351Multiple Airlines
Find Deal
Thu, 30 Oct - Mon, 3 Nov
WestJet Logo
6:20 a.m. - 10:30 a.m.YYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 a.m. - 4:50 p.m.MDW-YYZ
5h 15m1 stop
C$ 352WestJet
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Multiple Airlines Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
C$ 354Multiple Airlines
Find Deal
Tue, 21 Oct - Fri, 31 Oct
WestJet Logo
7:45 a.m. - 10:14 p.m.YYZ-MDW
15h 29m1 stop
WestJet Logo
1:48 p.m. - 11:18 p.m.MDW-YYZ
8h 30m1 stop
C$ 356WestJet
Find Deal
Mon, 13 Oct - Tue, 21 Oct
WestJet Logo
6:00 p.m. - 9:45 a.m.YYZ-MDW
16h 45m1 stop
WestJet Logo
10:40 a.m. - 9:55 p.m.MDW-YYZ
10h 15m1 stop
C$ 359WestJet
Find Deal
Wed, 29 Oct - Wed, 5 Nov
WestJet Logo
6:45 p.m. - 9:45 a.m.YYZ-MDW
16h 00m2 stops
WestJet Logo
10:40 a.m. - 4:50 p.m.MDW-YYZ
5h 10m1 stop
C$ 361WestJet
Find Deal
Wed, 29 Oct - Wed, 5 Nov
Delta Logo
12:15 p.m. - 6:25 p.m.YYZ-MDW
7h 10m1 stop
Delta Logo
9:35 a.m. - 2:45 p.m.MDW-YYZ
4h 10m1 stop
C$ 419Delta
Find Deal
Thu, 23 Oct - Wed, 29 Oct

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
23 Oct
YYZ12:15 p.m.Toronto Pearson Intl
7h 10m
1 stop
MDW6:25 p.m.Chicago Midway
29 Oct
MDW9:35 a.m.Chicago Midway
4h 10m
1 stop
YYZ2:45 p.m.Toronto Pearson Intl
C$ 419
Find similar
Delta
25 Sep
YYZ6:00 a.m.Toronto Pearson Intl
8h 03m
1 stop
MDW1:03 p.m.Chicago Midway
27 Sep
MDW6:15 p.m.Chicago Midway
3h 41m
1 stop
YYZ10:56 p.m.Toronto Pearson Intl
C$ 655
Find similar

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
18 Oct
YYZ6:20 a.m.Toronto Pearson Intl
5h 10m
1 stop
MDW10:30 a.m.Chicago Midway
25 Oct
MDW10:35 a.m.Chicago Midway
5h 15m
1 stop
YYZ4:50 p.m.Toronto Pearson Intl
C$ 326
Find similar
WestJet
18 Oct
YYZ6:20 a.m.Toronto Pearson Intl
5h 10m
1 stop
MDW10:30 a.m.Chicago Midway
25 Oct
MDW10:35 a.m.Chicago Midway
5h 15m
1 stop
YYZ4:50 p.m.Toronto Pearson Intl
C$ 352
Find similar
WestJet
13 Oct
YYZ7:45 a.m.Toronto Pearson Intl
15h 29m
1 stop
MDW10:14 p.m.Chicago Midway
21 Oct
MDW1:48 p.m.Chicago Midway
8h 30m
1 stop
YYZ11:18 p.m.Toronto Pearson Intl
C$ 356
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 16 September 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

Fri 7/11

12:50 p.m.-10:20 p.m.

1 stop10h 30m

Chicago Midway

Mon 10/11

8:00 a.m.-8:00 p.m.

1 stop11h 00m

C$ 305

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 18/10

6:20 a.m.-10:30 a.m.

1 stop5h 10m

Chicago Midway

Sat 25/10

10:35 a.m.-4:50 p.m.

1 stop5h 15m

C$ 326

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 16/10

6:00 p.m.-10:14 p.m.

1 stop5h 14m

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

C$ 350

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 30/10

5:15 p.m.-8:32 a.m.

1 stop16h 17m

Chicago Midway

Mon 3/11

9:32 a.m.-2:05 p.m.

1 stop27h 33m

C$ 351

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 18/10

6:20 a.m.-10:30 a.m.

1 stop5h 10m

Chicago Midway

Sat 25/10

10:35 a.m.-4:50 p.m.

1 stop5h 15m

C$ 352

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 21/10

6:00 p.m.-10:14 p.m.

1 stop5h 14m

Chicago Midway

Fri 31/10

9:32 a.m.-8:00 p.m.

1 stop9h 28m

C$ 354

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 13/10

7:45 a.m.-10:14 p.m.

1 stop15h 29m

Chicago Midway

Tue 21/10

1:48 p.m.-11:18 p.m.

1 stop8h 30m

C$ 356

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 29/10

6:00 p.m.-9:45 a.m.

1 stop16h 45m

Chicago Midway

Wed 5/11

10:40 a.m.-9:55 p.m.

1 stop10h 15m

C$ 359

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 29/10

6:45 p.m.-9:45 a.m.

2 stops16h 00m

Chicago Midway

Wed 5/11

10:40 a.m.-4:50 p.m.

1 stop5h 10m

C$ 361

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 23/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Wed 29/10

9:35 a.m.-2:45 p.m.

1 stop4h 10m

C$ 419

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 cheapest month to fly to Chicago Midway Airport?

In general, February 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$ 303. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Toronto Pearson Intl Airport during the month March is also very affordable. Most momondo users find prices during this month for around C$ 308.

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 Wednesday when prices can be found for as low as C$ 311. 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$ 332.

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$ 314. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 421.

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

Direct flights

None
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.
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  • 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 5h 10m, 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$ 228Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 421Free CancellationRating
7.2
3,093 reviews
Search WestJet flights

Travelling to a place near Chicago?

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

An easier way to manage your Chicago Midway Airport trip

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