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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 230

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 Midway Airport departing on 16/12. 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

These are some of the best round-trip flight deals from Toronto Pearson Intl Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto Pearson Intl Airport to Chicago.

Cheap last-minute flights

Planning a quick getaway from Toronto Pearson Intl Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Toronto Pearson Intl Airport to Chicago

Find recent round-trip train or bus tickets from Toronto Pearson Intl Airport to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
9:38 a.m. - 11:34 p.m.MDW-YYZ
12h 56m1 stop
C$ 373WestJet
Find Deal
Thu, 12 Dec - Mon, 16 Dec
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
11:19 a.m. - 11:11 p.m.MDW-YYZ
10h 52m1 stop
C$ 378WestJet
Find Deal
Tue, 7 Jan - Sat, 11 Jan
6:30 a.m. - 1:20 p.m.YYZ-MDW
7h 50m1 stop
9:20 a.m. - 6:23 p.m.MDW-YYZ
8h 03m1 stop
C$ 381WestJet
Find Deal
Sat, 12 Apr - Mon, 21 Apr
10:05 a.m. - 5:01 p.m.YYZ-MDW
7h 56m1 stop
5:50 p.m. - 10:36 p.m.MDW-YYZ
3h 46m1 stop
C$ 384Delta
Find Deal
Thu, 12 Dec - Mon, 16 Dec
2:55 p.m. - 1:31 p.m.YYZ-MDW
23h 36m1 stop
1:26 p.m. - 11:11 p.m.MDW-YYZ
8h 45m1 stop
C$ 388WestJet
Find Deal
Sat, 14 Dec - Fri, 10 Jan
6:30 a.m. - 5:47 p.m.YYZ-MDW
12h 17m1 stop
1:26 p.m. - 11:11 p.m.MDW-YYZ
8h 45m1 stop
C$ 399WestJet
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Thu, 20 Feb - Tue, 25 Feb
2:45 p.m. - 10:36 a.m.YYZ-MDW
20h 51m1 stop
6:59 p.m. - 1:48 p.m.MDW-YYZ
17h 49m1 stop
C$ 401WestJet
Find Deal
Fri, 10 Jan - Mon, 13 Jan
10:05 a.m. - 5:01 p.m.YYZ-MDW
7h 56m1 stop
5:50 p.m. - 10:36 p.m.MDW-YYZ
3h 46m1 stop
C$ 411Delta
Find Deal
Thu, 12 Dec - Mon, 16 Dec
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
2:08 p.m. - 10:52 p.m.MDW-YYZ
7h 44m1 stop
C$ 416Delta
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Sun, 12 Jan - Thu, 16 Jan
11:05 p.m. - 1:54 p.m.YYZ-MDW
15h 49m2 stops
5:15 a.m. - 2:42 p.m.MDW-YYZ
8h 27m1 stop
C$ 519
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Thu, 5 Dec - Sun, 8 Dec
12:30 p.m. - 5:01 p.m.YYZ-MDW
5h 31m1 stop
C$ 230Delta
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Mon, 16 Dec
12:25 p.m. - 10:06 p.m.YYZ-MDW
10h 41m1 stop
C$ 243WestJet
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Sat, 14 Dec
12:25 p.m. - 10:06 p.m.YYZ-MDW
10h 41m1 stop
C$ 244WestJet
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Sat, 14 Dec
10:10 a.m. - 1:08 p.m.YYZ-MDW
3h 58m1 stop
C$ 246Delta
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Mon, 6 Jan
6:30 a.m. - 5:47 p.m.YYZ-MDW
12h 17m1 stop
C$ 251WestJet
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Tue, 4 Feb
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
C$ 254WestJet
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Fri, 13 Dec
10:05 a.m. - 12:50 p.m.YYZ-MDW
3h 45m1 stop
C$ 256Delta
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Sun, 8 Dec
10:05 a.m. - 5:01 p.m.YYZ-MDW
7h 56m1 stop
C$ 257Delta
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Sun, 8 Dec
7:50 a.m. - 10:06 p.m.YYZ-MDW
15h 16m1 stop
C$ 258WestJet
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Sat, 14 Dec
12:21 p.m. - 9:46 p.m.YYZ-MDW
10h 25m1 stop
C$ 423Undisclosed Carrier
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Fri, 29 Nov
2:55 p.m. - 6:32 p.m.YYZ-MDW
4h 37m1 stop
9:30 a.m. - 11:41 p.m.MDW-YYZ
13h 11m1 stop
C$ 566WestJet
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Tue, 26 Nov - Tue, 3 Dec
2:55 p.m. - 6:32 p.m.YYZ-MDW
4h 37m1 stop
9:30 a.m. - 11:50 p.m.MDW-YYZ
13h 20m1 stop
C$ 609WestJet
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Mon, 25 Nov - Sat, 30 Nov
8:00 p.m. - 7:55 a.m.YYZ-MDW
12h 55m1 stop
12:43 p.m. - 7:06 p.m.MDW-YYZ
5h 23m1 stop
C$ 649
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Sun, 24 Nov - Tue, 3 Dec
2:55 p.m. - 6:32 p.m.YYZ-MDW
4h 37m1 stop
10:41 a.m. - 11:59 p.m.MDW-YYZ
12h 18m1 stop
C$ 656WestJet
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Tue, 26 Nov - Thu, 28 Nov
6:15 a.m. - 5:54 p.m.YYZ-MDW
12h 39m1 stop
9:30 a.m. - 11:50 p.m.MDW-YYZ
13h 20m1 stop
C$ 675WestJet
Find Deal
Tue, 26 Nov - Sat, 30 Nov
12:21 p.m. - 6:02 p.m.YYZ-MDW
6h 41m1 stop
12:44 p.m. - 7:06 p.m.MDW-YYZ
5h 22m1 stop
C$ 679WestJet
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Mon, 25 Nov - Mon, 9 Dec
6:15 a.m. - 5:54 p.m.YYZ-MDW
12h 39m1 stop
9:30 a.m. - 11:50 p.m.MDW-YYZ
13h 20m1 stop
C$ 684WestJet
Find Deal
Fri, 22 Nov - Sat, 30 Nov
6:00 a.m. - 12:49 p.m.YYZ-MDW
7h 49m1 stop
2:17 p.m. - 11:34 p.m.MDW-YYZ
8h 17m1 stop
C$ 716Delta
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Mon, 25 Nov - Sun, 1 Dec
6:30 a.m. - 1:37 p.m.YYZ-MDW
8h 07m1 stop
2:17 p.m. - 11:50 p.m.MDW-YYZ
8h 33m1 stop
C$ 857Delta
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Sun, 24 Nov - Sat, 30 Nov
6:00 a.m. - 8:50 a.m.YYZ-MDW
3h 50m1 stop
5:42 p.m. - 10:36 p.m.MDW-YYZ
3h 54m1 stop
C$ 1,074Delta
Find Deal
Sat, 23 Nov - Mon, 25 Nov

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
12 Dec
YYZ6:30 a.m.Toronto Pearson Intl
13h 02m
1 stop
MDW6:32 p.m.Chicago Midway
16 Dec
MDW9:38 a.m.Chicago Midway
12h 56m
1 stop
YYZ11:34 p.m.Toronto Pearson Intl
WestJet
7 Jan
YYZ6:30 a.m.Toronto Pearson Intl
7h 16m
1 stop
MDW12:46 p.m.Chicago Midway
11 Jan
MDW11:19 a.m.Chicago Midway
10h 52m
1 stop
YYZ11:11 p.m.Toronto Pearson Intl
WestJet
12 Apr
YYZ6:30 a.m.Toronto Pearson Intl
7h 50m
1 stop
MDW1:20 p.m.Chicago Midway
21 Apr
MDW9:20 a.m.Chicago Midway
8h 03m
1 stop
YYZ6:23 p.m.Toronto Pearson Intl

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
12 Dec
YYZ10:05 a.m.Toronto Pearson Intl
7h 56m
1 stop
MDW5:01 p.m.Chicago Midway
16 Dec
MDW5:50 p.m.Chicago Midway
3h 46m
1 stop
YYZ10:36 p.m.Toronto Pearson Intl
Delta
12 Dec
YYZ10:05 a.m.Toronto Pearson Intl
7h 56m
1 stop
MDW5:01 p.m.Chicago Midway
16 Dec
MDW5:50 p.m.Chicago Midway
3h 46m
1 stop
YYZ10:36 p.m.Toronto Pearson Intl
Delta
12 Jan
YYZ6:30 a.m.Toronto Pearson Intl
7h 16m
1 stop
MDW12:46 p.m.Chicago Midway
16 Jan
MDW2:08 p.m.Chicago Midway
7h 44m
1 stop
YYZ10:52 p.m.Toronto Pearson Intl

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, 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$ 295. If you are unable to visit Chicago Midway Airport during the month of December, 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$ 306.

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$ 338. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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$ 402.

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$ 365. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 405.

How far in advance should I book a flight to Chicago Midway Airport?

The best time to book a flight to Chicago Midway Airport from Toronto Pearson Intl Airport is 24 days out, which is when prices tend to be around C$ 363. Keep in mind that you might be able to find cheaper flights to Chicago Midway Airport at any time. In fact, our users found flights for as low as C$ 332 in the past 72 hours.

Can stopping save me money on Toronto Pearson Intl Airport to Chicago Midway Airport flights?

You could potentially save up to 20% on your flight if you consider stops on a Toronto Pearson Intl Airport to Chicago Midway Airport flight.

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

Best price found

C$ 230

Fastest flight time

3h 33m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Toronto Pearson Intl Airport in the past 72 hours is C$ 230. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 373.
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. Popular non-direct route for this connection is Toronto Pearson Intl Airport - 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 50m, 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$ 271Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 443Free CancellationRating
7.3
2,811 reviews
Search WestJet flights

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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