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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from $134

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 6/3. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Toronto Pearson Intl Airport to Chicago.
Delta Logo
12:15 pm - 6:45 pmYYZ-MDW
7h 30m1 stop
Delta Logo
9:16 am - 5:15 pmMDW-YYZ
6h 59m1 stop
$212Delta
Find Deal
Thu, May 22 - Mon, May 26
Delta Logo
12:54 pm - 5:19 pmYYZ-MDW
5h 25m1 stop
Delta Logo
6:25 pm - 10:58 pmMDW-YYZ
3h 33m1 stop
$224Delta
Find Deal
Tue, May 6 - Mon, May 12
Delta Logo
12:15 pm - 6:45 pmYYZ-MDW
7h 30m1 stop
Delta Logo
6:25 pm - 10:58 pmMDW-YYZ
3h 33m1 stop
$225Delta
Find Deal
Wed, May 7 - Mon, May 12
Delta Logo
12:15 pm - 6:28 pmYYZ-MDW
7h 13m1 stop
Delta Logo
5:45 pm - 10:55 pmMDW-YYZ
4h 10m1 stop
$231Delta
Find Deal
Thu, Jul 17 - Sat, Jul 19
Delta Logo
12:15 pm - 6:45 pmYYZ-MDW
7h 30m1 stop
Delta Logo
9:20 am - 6:31 pmMDW-YYZ
8h 11m1 stop
$232Delta
Find Deal
Thu, May 29 - Sun, Jun 1
KLM Logo
12:15 pm - 6:45 pmYYZ-MDW
7h 30m1 stop
KLM Logo
6:25 pm - 10:58 pmMDW-YYZ
3h 33m1 stop
$235KLM
Find Deal
Fri, May 9 - Sun, May 11
WestJet Logo
12:30 pm - 5:45 pmYYZ-MDW
6h 15m1 stop
WestJet Logo
12:48 pm - 9:56 pmMDW-YYZ
8h 08m1 stop
$283WestJet
Find Deal
Wed, May 21 - Wed, May 28
WestJet Logo
12:30 pm - 5:45 pmYYZ-MDW
6h 15m1 stop
WestJet Logo
1:55 pm - 11:14 pmMDW-YYZ
8h 19m1 stop
$284WestJet
Find Deal
Tue, May 20 - Tue, May 27
 Logo
6:10 pm - 10:22 pmYYZ-MDW
5h 12m1 stop
 Logo
10:55 am - 7:55 amMDW-YYZ
20h 00m2 stops
Fri, May 2 - Sun, May 4
 Logo
8:00 pm - 9:40 amYYZ-MDW
14h 40m2 stops
 Logo
9:12 pm - 10:44 pmMDW-YYZ
24h 32m1 stop
Thu, May 22 - Mon, May 26

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
May 21
YYZ12:30 pmToronto Pearson Intl
6h 15m
1 stop
MDW5:45 pmChicago Midway
May 28
MDW12:48 pmChicago Midway
8h 08m
1 stop
YYZ9:56 pmToronto Pearson Intl
WestJet
May 20
YYZ12:30 pmToronto Pearson Intl
6h 15m
1 stop
MDW5:45 pmChicago Midway
May 27
MDW1:55 pmChicago Midway
8h 19m
1 stop
YYZ11:14 pmToronto Pearson Intl
WestJet
May 17
YYZ11:30 amToronto Pearson Intl
10h 44m
1 stop
MDW9:14 pmChicago Midway
May 31
MDW12:48 pmChicago Midway
10h 07m
1 stop
YYZ11:55 pmToronto 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
May 22
YYZ12:15 pmToronto Pearson Intl
7h 30m
1 stop
MDW6:45 pmChicago Midway
May 26
MDW9:16 amChicago Midway
6h 59m
1 stop
YYZ5:15 pmToronto Pearson Intl
Delta
May 6
YYZ12:54 pmToronto Pearson Intl
5h 25m
1 stop
MDW5:19 pmChicago Midway
May 12
MDW6:25 pmChicago Midway
3h 33m
1 stop
YYZ10:58 pmToronto Pearson Intl
Delta
May 7
YYZ12:15 pmToronto Pearson Intl
7h 30m
1 stop
MDW6:45 pmChicago Midway
May 12
MDW6:25 pmChicago Midway
3h 33m
1 stop
YYZ10:58 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 $219. 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 $223.

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

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Toronto Pearson Intl Airport. The lowest ticket price found for a Monday departure recently was $252. 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, Tuesday 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 $292.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $252 when looking at flights departing in the evening. 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

$134

Fastest flight time

3h 10m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Toronto Pearson Intl Airport in the past 72 hours is $134. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $212.
The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 10m
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 10m 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.


Traveling to a place near Chicago?

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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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