Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from $140

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 5/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

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
6:00 am - 8:40 amYYZ-MDW
3h 40m1 stop
Delta Logo
9:20 am - 3:09 pmMDW-YYZ
4h 49m1 stop
$224Delta
Find Deal
Thu, Apr 24 - Sun, Apr 27
Delta Logo
3:59 pm - 6:20 pmYYZ-MDW
3h 21m1 stop
Delta Logo
5:59 pm - 10:55 pmMDW-YYZ
3h 56m1 stop
$231Delta
Find Deal
Sat, Apr 26 - Wed, Apr 30
Delta Logo
12:15 pm - 6:20 pmYYZ-MDW
7h 05m1 stop
Delta Logo
6:25 pm - 10:58 pmMDW-YYZ
3h 33m1 stop
$232Delta
Find Deal
Thu, May 1 - Wed, May 7
Delta Logo
6:30 am - 8:40 amYYZ-MDW
3h 10m1 stop
Delta Logo
9:20 am - 6:27 pmMDW-YYZ
8h 07m1 stop
$245Delta
Find Deal
Wed, May 14 - Thu, Aug 14
Delta Logo
3:59 pm - 6:20 pmYYZ-MDW
3h 21m1 stop
Delta Logo
9:20 am - 3:09 pmMDW-YYZ
4h 49m1 stop
$250Delta
Find Deal
Thu, Apr 24 - Sun, Apr 27
Delta Logo
6:00 am - 8:40 amYYZ-MDW
3h 40m1 stop
Delta Logo
10:20 am - 6:31 pmMDW-YYZ
7h 11m1 stop
$253Delta
Find Deal
Thu, Apr 24 - Mon, Apr 28
WestJet Logo
8:00 pm - 9:40 amYYZ-MDW
14h 40m2 stops
WestJet Logo
9:20 am - 6:31 pmMDW-YYZ
8h 11m1 stop
$291WestJet
Find Deal
Sat, May 24 - Tue, May 27
WestJet Logo
1:27 pm - 5:59 pmYYZ-MDW
5h 32m1 stop
WestJet Logo
10:20 am - 6:31 pmMDW-YYZ
7h 11m1 stop
$293WestJet
Find Deal
Fri, Apr 25 - Tue, Apr 29
WestJet Logo
1:25 pm - 9:13 pmYYZ-MDW
8h 48m1 stop
WestJet Logo
1:57 pm - 11:21 pmMDW-YYZ
8h 24m1 stop
$295WestJet
Find Deal
Sat, Jun 7 - Tue, Jun 10
 Logo
10:15 am - 10:36 pmYYZ-MDW
13h 21m1 stop
 Logo
12:46 pm - 1:55 pmMDW-YYZ
24h 09m1 stop
Sat, Apr 12 - Sun, Apr 13

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
Apr 24
YYZ6:00 amToronto Pearson Intl
3h 40m
1 stop
MDW8:40 amChicago Midway
Apr 27
MDW9:20 amChicago Midway
4h 49m
1 stop
YYZ3:09 pmToronto Pearson Intl
Delta
Apr 26
YYZ3:59 pmToronto Pearson Intl
3h 21m
1 stop
MDW6:20 pmChicago Midway
Apr 30
MDW5:59 pmChicago Midway
3h 56m
1 stop
YYZ10:55 pmToronto Pearson Intl
Delta
May 1
YYZ12:15 pmToronto Pearson Intl
7h 05m
1 stop
MDW6:20 pmChicago Midway
May 7
MDW6:25 pmChicago Midway
3h 33m
1 stop
YYZ10:58 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
May 24
YYZ8:00 pmToronto Pearson Intl
14h 40m
2 stops
MDW9:40 amChicago Midway
May 27
MDW9:20 amChicago Midway
8h 11m
1 stop
YYZ6:31 pmToronto Pearson Intl
WestJet
Apr 25
YYZ1:27 pmToronto Pearson Intl
5h 32m
1 stop
MDW5:59 pmChicago Midway
Apr 29
MDW10:20 amChicago Midway
7h 11m
1 stop
YYZ6:31 pmToronto Pearson Intl
WestJet
Jun 7
YYZ1:25 pmToronto Pearson Intl
8h 48m
1 stop
MDW9:13 pmChicago Midway
Jun 10
MDW1:57 pmChicago Midway
8h 24m
1 stop
YYZ11:21 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 December is also very affordable. Most momondo users find prices during this month for around $279.

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

$140

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 $140. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $224.
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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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.


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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Sun 4/6
Sun 4/13

Find better results for your trip to Chicago