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Cheap flights from Toronto to Chicago Midway Airport from C$ 189

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 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 to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Toronto 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 to Chicago.

Cheap last-minute flights

Planning a quick getaway from Toronto 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 to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 307Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 312Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 365Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
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$ 374WestJet
Find Deal
Thu, 12 Dec - Mon, 16 Dec
6:30 a.m. - 6:11 p.m.YYZ-MDW
12h 41m1 stop
9:20 a.m. - 6:23 p.m.MDW-YYZ
8h 03m1 stop
C$ 381WestJet
Find Deal
Sat, 12 Apr - Mon, 21 Apr
10:10 a.m. - 1:08 p.m.YYZ-MDW
3h 58m1 stop
2:08 p.m. - 10:52 p.m.MDW-YYZ
7h 44m1 stop
C$ 414Delta
Find Deal
Mon, 27 Jan - Wed, 29 Jan
6:30 a.m. - 10:36 a.m.YYZ-MDW
5h 06m1 stop
6:28 p.m. - 10:52 p.m.MDW-YYZ
3h 24m1 stop
C$ 417Delta
Find Deal
Sat, 18 Jan - Mon, 20 Jan
8:55 p.m. - 5:37 p.m.YTZ-MDW
21h 42m1 stop
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 486
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:15 a.m. - 4:58 p.m.MDW-YTZ
10h 43m2 stops
C$ 491
Find Deal
Fri, 6 Dec - Sun, 8 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
C$ 189Porter Airlines
Find Deal
Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 190Porter Airlines
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Thu, 19 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 217Air Transat
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Tue, 17 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
C$ 228Air Transat
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Wed, 18 Dec
6:00 a.m. - 12:50 p.m.YYZ-MDW
7h 50m1 stop
C$ 230Delta
Find Deal
Mon, 16 Dec
10:10 a.m. - 1:08 p.m.YYZ-MDW
3h 58m1 stop
C$ 245Delta
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Mon, 6 Jan
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
C$ 249WestJet
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Thu, 6 Feb
8:15 p.m. - 9:55 a.m.YYZ-MDW
14h 40m1 stop
C$ 251
Find Deal
Tue, 17 Dec
6:30 a.m. - 10:36 a.m.YYZ-MDW
5h 06m1 stop
C$ 255WestJet
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Sun, 19 Jan
8:00 p.m. - 11:48 a.m.YYZ-MDW
16h 48m1 stop
C$ 260
Find Deal
Wed, 4 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 538Porter Airlines
Find Deal
Fri, 22 Nov - Tue, 3 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 550Porter Airlines
Find Deal
Sun, 24 Nov - Tue, 3 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 575Air Transat
Find Deal
Mon, 25 Nov - Tue, 3 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 601Air Transat
Find Deal
Sun, 24 Nov - Tue, 3 Dec
6:00 a.m. - 12:49 p.m.YYZ-MDW
7h 49m1 stop
1:30 p.m. - 10:36 p.m.MDW-YYZ
8h 06m1 stop
C$ 619Delta
Find Deal
Mon, 25 Nov - Tue, 3 Dec
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$ 651
Find Deal
Sun, 24 Nov - Tue, 3 Dec
6:15 p.m. - 9:32 a.m.YYZ-MDW
16h 17m1 stop
7:17 p.m. - 1:41 p.m.MDW-YYZ
17h 24m1 stop
C$ 657WestJet
Find Deal
Fri, 22 Nov - Fri, 29 Nov
6:15 p.m. - 9:32 a.m.YYZ-MDW
16h 17m1 stop
9:30 a.m. - 11:50 p.m.MDW-YYZ
13h 20m1 stop
C$ 659WestJet
Find Deal
Fri, 22 Nov - Sat, 30 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 697
Find Deal
Mon, 25 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$ 718Delta
Find Deal
Mon, 25 Nov - Sun, 1 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 307Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 312Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 314Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 319Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 332Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 335Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 365Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 367Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 577
Find Deal
Sat, 21 Dec - Sun, 5 Jan

Delta flights from Toronto to Chicago Midway Airport

Our best Delta deals on Toronto to Chicago Midway Airport flight tickets
Delta
27 Jan
YYZ10:10 a.m.Toronto Pearson Intl
3h 58m
1 stop
MDW1:08 p.m.Chicago Midway
29 Jan
MDW2:08 p.m.Chicago Midway
7h 44m
1 stop
YYZ10:52 p.m.Toronto Pearson Intl
Delta
18 Jan
YYZ6:30 a.m.Toronto Pearson Intl
5h 06m
1 stop
MDW10:36 a.m.Chicago Midway
20 Jan
MDW6:28 p.m.Chicago Midway
3h 24m
1 stop
YYZ10:52 p.m.Toronto Pearson Intl
Delta
13 Jan
YYZ10:10 a.m.Toronto Pearson Intl
3h 58m
1 stop
MDW1:08 p.m.Chicago Midway
12 Feb
MDW2:08 p.m.Chicago Midway
4h 01m
1 stop
YYZ7:09 p.m.Toronto Pearson Intl

Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Porter Airlines
12 Dec
YTZ3:50 p.m.Toronto Island
1h 50m
MDW4:40 p.m.Chicago Midway
15 Dec
MDW5:35 p.m.Chicago Midway
1h 42m
YTZ8:17 p.m.Toronto Island
Porter Airlines
12 Dec
YTZ3:50 p.m.Toronto Island
1h 50m
MDW4:40 p.m.Chicago Midway
15 Dec
MDW5:35 p.m.Chicago Midway
1h 42m
YTZ8:17 p.m.Toronto Island
Porter Airlines
12 Dec
YTZ3:50 p.m.Toronto Island
1h 50m
MDW4:40 p.m.Chicago Midway
15 Dec
MDW5:35 p.m.Chicago Midway
1h 42m
YTZ8:17 p.m.Toronto Island

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto 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 from Toronto to Chicago Midway Airport?

December. The cheapest time of year to fly to Chicago Midway Airport from Toronto is December. The most expensive is February.

What is the cheapest day to depart Toronto for Chicago Midway Airport?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Monday

When is the cheapest time to fly from Toronto to Chicago Midway Airport?

In the morning. Toronto to Chicago Midway Airport flights are approximately 10% more expensive at noon than in the morning

How far in advance should you book Toronto to Chicago Midway Airport flights?

24 days before. The cheapest time to buy a flight from Toronto to Chicago Midway Airport is approximately 24 days to departure

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

No. A direct flight is the cheapest option for a flight between Toronto to Chicago Midway Airport.

How have Toronto to Chicago Midway Airport flight prices changed over time?

What is the typical price of a round-trip flight between Toronto and Chicago Midway Airport?


When to book flights from Toronto to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto 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 to Chicago Midway Airport (YTO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago Midway Airport

Best price found

C$ 189

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is C$ 189. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is C$ 307.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 50m
Direct flights go from Toronto to Chicago Midway Airport every day.

  • How far is Toronto to Chicago Midway by plane?

    There are 713.1 km between Toronto and Chicago Midway. By plane, this route typically takes 1h 50m.

  • When did momondo last update prices for flights from Toronto to Chicago Midway Airport?

    Prices for flights from Toronto to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Toronto to Chicago Midway Airport?

  • How old do you have to be to fly from Toronto 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 to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Toronto to Chicago Midway Airport?

  • What is the most popular airline from Toronto to Chicago Midway Airport?


Best airlines flying from Toronto to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto 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$ 444Free CancellationRating
7.3
2,811 reviews
Search WestJet flights
  • Porter Airlines Flights From Toronto to Chicago Midway Airport

    Porter Airlines flight deals from Toronto to Chicago Midway Airport start from C$ 194 round-trip. Over the 9 Porter Airlines flights for this route in a normal week, average airfare is usually C$ 261 round-trip - but some users have found much cheaper deals with momondo.


Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Chicago for you.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.

How can momondo help me find flights from Toronto to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


An easier way to manage your Chicago Midway Airport trip

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