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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from $146

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 1/16. 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.
7:00 am - 12:09 pmYYZ-MDW
30h 09m1 stop
8:45 am - 5:15 pmMDW-YYZ
31h 30m2 stops
Thu, Jan 30 - Sun, Feb 2
10:10 am - 1:05 pmYYZ-MDW
3h 55m1 stop
9:33 am - 4:09 pmMDW-YYZ
5h 36m1 stop
$264Delta
Find Deal
Mon, Feb 17 - Tue, Feb 25
1:20 pm - 6:14 pmYYZ-MDW
5h 54m1 stop
9:34 am - 4:12 pmMDW-YYZ
5h 38m1 stop
$265Delta
Find Deal
Thu, Jan 30 - Sun, Feb 2
6:00 am - 8:54 amYYZ-MDW
3h 54m1 stop
6:28 pm - 10:49 pmMDW-YYZ
3h 21m1 stop
$282Delta
Find Deal
Mon, Jan 27 - Tue, Feb 4
1:20 pm - 4:09 pmYYZ-MDW
3h 49m1 stop
1:26 pm - 11:07 pmMDW-YYZ
8h 41m1 stop
$287Delta
Find Deal
Sat, Mar 1 - Wed, Mar 5
6:00 am - 8:51 amYYZ-MDW
3h 51m1 stop
9:33 am - 4:09 pmMDW-YYZ
5h 36m1 stop
$288Delta
Find Deal
Thu, Feb 20 - Thu, Feb 27
7:40 am - 3:21 pmYYZ-MDW
8h 41m1 stop
7:25 am - 5:30 pmMDW-YYZ
9h 05m1 stop
Sun, Feb 2 - Thu, Feb 6
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
1:26 pm - 11:11 pmMDW-YYZ
8h 45m1 stop
$316WestJet
Find Deal
Thu, Jan 30 - Sun, Feb 2
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
1:26 pm - 11:07 pmMDW-YYZ
8h 41m1 stop
$322WestJet
Find Deal
Fri, Jan 31 - Wed, Feb 5
6:30 am - 12:42 pmYYZ-MDW
7h 12m1 stop
1:26 pm - 11:07 pmMDW-YYZ
8h 41m1 stop
$330WestJet
Find Deal
Fri, Feb 21 - Mon, Feb 24
10:00 am - 11:44 amYYZ-MDW
26h 44m2 stops
Thu, Jan 16
8:00 pm - 11:44 amYYZ-MDW
16h 44m1 stop
Thu, Jan 16
7:00 am - 3:43 pmYYZ-MDW
9h 43m2 stops
Mon, Feb 3
10:10 am - 1:08 pmYYZ-MDW
3h 58m1 stop
$159Delta
Find Deal
Sun, Feb 2
6:00 am - 8:54 amYYZ-MDW
3h 54m1 stop
$160Delta
Find Deal
Thu, Jan 30
7:40 am - 3:21 pmYYZ-MDW
8h 41m1 stop
Sun, Feb 9
10:20 am - 12:36 pmYYZ-MDW
3h 16m1 stop
$171Delta
Find Deal
Mon, Mar 24
6:30 am - 10:42 amYYZ-MDW
5h 12m1 stop
$182WestJet
Find Deal
Sat, Feb 8
7:00 pm - 10:12 amYYZ-MDW
16h 12m2 stops
$188WestJet
Find Deal
Sat, Feb 8
6:30 am - 5:47 pmYYZ-MDW
12h 17m1 stop
$200WestJet
Find Deal
Sun, Feb 2
7:00 am - 3:16 pmYYZ-MDW
9h 16m1 stop
10:58 am - 7:30 pmMDW-YYZ
7h 32m1 stop
Sun, Jan 12 - Sun, Jan 19
10:10 am - 1:08 pmYYZ-MDW
3h 58m1 stop
2:08 pm - 10:52 pmMDW-YYZ
7h 44m1 stop
$397Delta
Find Deal
Tue, Jan 14 - Wed, Jan 29
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
1:26 pm - 11:11 pmMDW-YYZ
8h 45m1 stop
$419WestJet
Find Deal
Sun, Jan 12 - Fri, Jan 31
6:00 am - 1:08 pmYYZ-MDW
8h 08m1 stop
2:08 pm - 7:09 pmMDW-YYZ
4h 01m1 stop
$446Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
10:10 am - 1:08 pmYYZ-MDW
3h 58m1 stop
2:08 pm - 7:09 pmMDW-YYZ
4h 01m1 stop
$479Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
12:44 pm - 11:55 pmMDW-YYZ
10h 11m1 stop
$485WestJet
Find Deal
Mon, Jan 13 - Thu, Jan 30
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
1:26 pm - 11:11 pmMDW-YYZ
8h 45m1 stop
$486WestJet
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
10:19 am - 11:11 pmMDW-YYZ
11h 52m1 stop
$490WestJet
Find Deal
Fri, Jan 10 - Sun, Jan 12
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
10:57 am - 5:00 pmMDW-YYZ
5h 03m1 stop
$492WestJet
Find Deal
Tue, Jan 14 - Wed, Jan 15
11:05 pm - 5:47 pmYYZ-MDW
19h 42m2 stops
1:26 pm - 8:11 amMDW-YYZ
17h 45m2 stops
$1,582
Find Deal
Fri, Jan 10 - Sun, Jan 12

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
Feb 17
YYZ10:10 amToronto Pearson Intl
3h 55m
1 stop
MDW1:05 pmChicago Midway
Feb 25
MDW9:33 amChicago Midway
5h 36m
1 stop
YYZ4:09 pmToronto Pearson Intl
Delta
Jan 30
YYZ1:20 pmToronto Pearson Intl
5h 54m
1 stop
MDW6:14 pmChicago Midway
Feb 2
MDW9:34 amChicago Midway
5h 38m
1 stop
YYZ4:12 pmToronto Pearson Intl
Delta
Jan 27
YYZ6:00 amToronto Pearson Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
Feb 4
MDW6:28 pmChicago Midway
3h 21m
1 stop
YYZ10:49 pmToronto Pearson Intl

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
Jan 30
YYZ6:30 amToronto Pearson Intl
7h 16m
1 stop
MDW12:46 pmChicago Midway
Feb 2
MDW1:26 pmChicago Midway
8h 45m
1 stop
YYZ11:11 pmToronto Pearson Intl
WestJet
Jan 31
YYZ6:30 amToronto Pearson Intl
7h 16m
1 stop
MDW12:46 pmChicago Midway
Feb 5
MDW1:26 pmChicago Midway
8h 41m
1 stop
YYZ11:07 pmToronto Pearson Intl
WestJet
Feb 21
YYZ6:30 amToronto Pearson Intl
7h 12m
1 stop
MDW12:42 pmChicago Midway
Feb 24
MDW1:26 pmChicago Midway
8h 41m
1 stop
YYZ11:07 pmToronto 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?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto Pearson Intl Airport, with most prices found around $246. If you are unable to visit Chicago Midway Airport during the month of February, 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 $274.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Toronto Pearson Intl Airport. The lowest ticket price found for a Wednesday departure recently was $228. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 travelers. As a result, prices tend to be around $385.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Toronto Pearson Intl Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $253 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $284. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

$146

Fastest flight time

3h 15m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Toronto Pearson Intl Airport in the past 72 hours is $146. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $248.
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. 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 432.2 mi. 3h 15m is a normal flight duration for this route.

  • 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 refresh daily.

  • How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Pearson Intl Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


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?

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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?

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.


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