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Cheap flights from Toronto to Chicago Midway Airport from C$ 170

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 31/1. 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.
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 281Porter Airlines
Find Deal
qua, 15 jan - sex, 17 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 286Porter Airlines
Find Deal
sex, 17 jan - seg, 20 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 334Air Transat
Find Deal
qui, 9 jan - dom, 12 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 336Air Transat
Find Deal
qui, 9 jan - dom, 12 jan
6:00 a.m. - 8:54 a.m.YYZ-MDW
3h 54m1 stop
6:28 p.m. - 10:49 p.m.MDW-YYZ
3h 21m1 stop
C$ 351Delta
Find Deal
ter, 7 jan - seg, 3 fev
6:00 a.m. - 8:54 a.m.YYZ-MDW
3h 54m1 stop
9:34 a.m. - 4:12 p.m.MDW-YYZ
5h 38m1 stop
C$ 357Delta
Find Deal
ter, 14 jan - sex, 17 jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 384
Find Deal
seg, 6 jan - sex, 7 fev
12:20 p.m. - 10:12 a.m.YYZ-MDW
22h 52m1 stop
10:19 a.m. - 11:11 p.m.MDW-YYZ
11h 52m1 stop
C$ 391WestJet
Find Deal
qui, 9 jan - dom, 12 jan
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
10:19 a.m. - 11:11 p.m.MDW-YYZ
11h 52m1 stop
C$ 403WestJet
Find Deal
ter, 7 jan - qua, 15 jan
8:00 p.m. - 11:48 a.m.YYZ-MDW
16h 48m1 stop
12:43 p.m. - 6:18 a.m.MDW-YYZ
16h 35m2 stops
C$ 460
Find Deal
qui, 9 jan - dom, 12 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 170Porter Airlines
Find Deal
sex, 31 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 171Porter Airlines
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sex, 31 jan
7:45 a.m. - 1:08 p.m.YYZ-MDW
6h 23m1 stop
C$ 200Delta
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qua, 29 jan
7:45 a.m. - 1:08 p.m.YYZ-MDW
6h 23m1 stop
C$ 217Delta
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sex, 31 jan
9:25 a.m. - 12:54 a.m.YYZ-MDW
16h 29m2 stops
C$ 229
Find Deal
sex, 24 jan
6:30 a.m. - 5:47 p.m.YYZ-MDW
12h 17m1 stop
C$ 237WestJet
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sex, 10 jan
7:55 p.m. - 9:51 p.m.YYZ-MDW
26h 56m1 stop
C$ 239
Find Deal
ter, 11 mar
6:30 a.m. - 2:15 p.m.YYZ-MDW
8h 45m1 stop
C$ 241WestJet
Find Deal
ter, 18 mar
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
C$ 277Air Transat
Find Deal
sáb, 4 jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 358Air Transat
Find Deal
qua, 25 dez
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$ 554Porter Airlines
Find Deal
sáb, 21 dez - ter, 31 dez
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$ 557Porter Airlines
Find Deal
dom, 22 dez - qui, 2 jan
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 581Porter Airlines
Find Deal
qui, 19 dez - sex, 3 jan
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$ 586Porter Airlines
Find Deal
qui, 19 dez - sáb, 4 jan
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$ 690
Find Deal
qui, 19 dez - sex, 3 jan
1:15 p.m. - 5:44 p.m.YYZ-MDW
5h 29m1 stop
4:50 p.m. - 11:08 p.m.MDW-YYZ
5h 18m1 stop
C$ 716WestJet
Find Deal
seg, 23 dez - qua, 25 dez
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
6:00 a.m. - 6:53 p.m.MDW-YTZ
11h 53m2 stops
C$ 747
Find Deal
sex, 20 dez - sex, 27 dez
1:15 p.m. - 5:44 p.m.YYZ-MDW
5h 29m1 stop
4:50 p.m. - 11:08 p.m.MDW-YYZ
5h 18m1 stop
C$ 753WestJet
Find Deal
seg, 23 dez - ter, 24 dez
10:05 a.m. - 4:24 p.m.YYZ-MDW
7h 19m1 stop
9:30 a.m. - 4:14 p.m.MDW-YYZ
5h 44m1 stop
C$ 823Delta
Find Deal
qui, 19 dez - qui, 26 dez
10:05 a.m. - 4:24 p.m.YYZ-MDW
7h 19m1 stop
9:30 a.m. - 4:14 p.m.MDW-YYZ
5h 44m1 stop
C$ 967Delta
Find Deal
qui, 19 dez - dom, 5 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 281Porter Airlines
Find Deal
qua, 15 jan - sex, 17 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 286Porter Airlines
Find Deal
sex, 24 jan - dom, 26 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 287Porter Airlines
Find Deal
qua, 15 jan - dom, 19 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 289Porter Airlines
Find Deal
qua, 15 jan - dom, 19 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 290Porter Airlines
Find Deal
dom, 19 jan - qui, 30 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 291Porter Airlines
Find Deal
qui, 9 jan - dom, 12 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 334Air Transat
Find Deal
qui, 9 jan - dom, 12 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 336Air Transat
Find Deal
qui, 9 jan - dom, 12 jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 354Air Transat
Find Deal
qui, 9 jan - dom, 12 jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 384
Find Deal
seg, 6 jan - sex, 7 fev

Air Transat flights from Toronto to Chicago Midway Airport

Our best Air Transat deals on Toronto to Chicago Midway Airport flight tickets
Air Transat
9 Jan
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
12 Jan
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Air Transat
9 Jan
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
12 Jan
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Air Transat
9 Jan
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
12 Jan
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island

WestJet flights from Toronto to Chicago Midway Airport

Our best WestJet deals on Toronto to Chicago Midway Airport flight tickets
WestJet
9 Jan
YYZ12:20 p.m.Toronto Pearson Intl
22h 52m
1 stop
MDW10:12 a.m.Chicago Midway
12 Jan
MDW10:19 a.m.Chicago Midway
11h 52m
1 stop
YYZ11:11 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
15 Jan
MDW10:19 a.m.Chicago Midway
11h 52m
1 stop
YYZ11:11 p.m.Toronto Pearson Intl
WestJet
7 Jan
YYZ6:30 a.m.Toronto Pearson Intl
12h 17m
1 stop
MDW5:47 p.m.Chicago Midway
15 Jan
MDW1:26 p.m.Chicago Midway
8h 45m
1 stop
YYZ11:11 p.m.Toronto Pearson Intl

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 typical price of a round-trip flight between Toronto 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 to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 313. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Toronto during the month July is also very affordable. Most momondo users find prices during this month for around C$ 333.

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$ 346. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 421.

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 evening. Flights from Toronto to Chicago Midway Airport during this time can be as low as C$ 374. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 592.

What is the cheapest Toronto to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago Midway flight prices

What cabin class options are available on Toronto to Chicago Midway flights?

There are 1 cabin classes available to choose from on Toronto to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 17% on your flight if you consider stops on a Toronto to Chicago Midway Airport flight.

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


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$ 170

Fastest flight time

1h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is C$ 170. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is C$ 281.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 45m
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 45m.

  • 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$ 277Free CancellationRating
7.9
283 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 453Free CancellationRating
7.2
2,818 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 12 Porter Airlines flights for this route in a normal week, average airfare is usually C$ 265 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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