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Cheap flights from Toronto Pearson Intl Airport to Chicago from $150

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 departing on 9/6. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:15 pm - 6:31 pm
YYZ
-
MDW
7h 16m
1 stop
Delta Logo
9:30 am - 5:20 pm
MDW
-
YYZ
6h 50m
1 stop
$240Delta
Fri, Sep 11 - Mon, Sep 14
KLM Logo
6:10 am - 9:13 am
YYZ
-
MDW
4h 03m
1 stop
KLM Logo
9:19 am - 5:24 pm
MDW
-
YYZ
7h 05m
1 stop
$243KLM
Wed, Jul 15 - Wed, Jul 22
Delta Logo
12:09 pm - 6:25 pm
YYZ
-
MDW
7h 16m
1 stop
Delta Logo
9:19 am - 5:24 pm
MDW
-
YYZ
7h 05m
1 stop
$244Delta
Fri, Jul 10 - Tue, Jul 28
Delta Logo
6:05 am - 12:46 pm
YYZ
-
MDW
7h 41m
1 stop
Delta Logo
1:26 pm - 11:02 pm
MDW
-
YYZ
8h 36m
1 stop
$252Delta
Wed, Jul 1 - Thu, Jul 2
WestJet Logo
6:15 am - 12:44 pm
YYZ
-
MDW
7h 29m
1 stop
WestJet Logo
6:47 pm - 11:04 pm
MDW
-
YYZ
3h 17m
1 stop
$257WestJet
Sat, Aug 8 - Sat, Aug 8
Delta Logo
6:00 am - 12:34 pm
YYZ
-
MDW
7h 34m
1 stop
Delta Logo
9:30 am - 5:20 pm
MDW
-
YYZ
6h 50m
1 stop
$259Delta
Thu, Sep 17 - Sat, Sep 19
Delta Logo
4:05 pm - 6:33 pm
YYZ
-
MDW
3h 28m
1 stop
Delta Logo
9:30 am - 5:20 pm
MDW
-
YYZ
6h 50m
1 stop
$260Delta
Tue, Sep 22 - Wed, Sep 30
WestJet Logo
12:14 pm - 6:36 pm
YYZ
-
MDW
7h 22m
1 stop
WestJet Logo
9:22 am - 3:24 pm
MDW
-
YYZ
5h 02m
1 stop
$269WestJet
Tue, Jun 23 - Sat, Jun 27
Delta Logo
6:00 am - 12:33 pm
YYZ
-
MDW
7h 33m
1 stop
Delta Logo
9:30 am - 5:22 pm
MDW
-
YYZ
6h 52m
1 stop
$270Delta
Thu, Oct 8 - Tue, Oct 13
Delta Logo
9:45 am - 12:46 pm
YYZ
-
MDW
4h 01m
1 stop
Delta Logo
9:17 am - 3:19 pm
MDW
-
YYZ
5h 02m
1 stop
$275Delta
Tue, Jun 30 - Fri, Jul 3

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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
Sep 11
YYZ12:15 pmToronto Pearson Intl
7h 16m
1 stop
MDW6:31 pmChicago Midway
Sep 14
MDW9:30 amChicago Midway
6h 50m
1 stop
YYZ5:20 pmToronto Pearson Intl
$240
Delta
Jul 10
YYZ12:09 pmToronto Pearson Intl
7h 16m
1 stop
MDW6:25 pmChicago Midway
Jul 28
MDW9:19 amChicago Midway
7h 05m
1 stop
YYZ5:24 pmToronto Pearson Intl
$244
Delta
Jul 1
YYZ6:05 amToronto Pearson Intl
7h 41m
1 stop
MDW12:46 pmChicago Midway
Jul 2
MDW1:26 pmChicago Midway
8h 36m
1 stop
YYZ11:02 pmToronto Pearson Intl
$252

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
Aug 8
YYZ6:15 amToronto Pearson Intl
7h 29m
1 stop
MDW12:44 pmChicago Midway
Aug 8
MDW6:47 pmChicago Midway
3h 17m
1 stop
YYZ11:04 pmToronto Pearson Intl
$257
WestJet
Jun 23
YYZ12:14 pmToronto Pearson Intl
7h 22m
1 stop
MDW6:36 pmChicago Midway
Jun 27
MDW9:22 amChicago Midway
5h 02m
1 stop
YYZ3:24 pmToronto Pearson Intl
$269
WestJet
Jul 31
YYZ12:14 pmToronto Pearson Intl
7h 16m
1 stop
MDW6:30 pmChicago Midway
Aug 4
MDW1:32 pmChicago Midway
8h 36m
1 stop
YYZ11:08 pmToronto Pearson Intl
$309

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Pearson Intl Airport to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 13, 2026.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/11

12:15 pm-6:31 pm

1 stop7h 16m

Chicago Midway

Mon 9/14

9:30 am-5:20 pm

1 stop6h 50m

$240

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 7/15

6:10 am-9:13 am

1 stop4h 03m

Chicago Midway

Wed 7/22

9:19 am-5:24 pm

1 stop7h 05m

$243

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 7/10

12:09 pm-6:25 pm

1 stop7h 16m

Chicago Midway

Tue 7/28

9:19 am-5:24 pm

1 stop7h 05m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 7/1

6:05 am-12:46 pm

1 stop7h 41m

Chicago Midway

Thu 7/2

1:26 pm-11:02 pm

1 stop8h 36m

$252

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 8/8

6:15 am-12:44 pm

1 stop7h 29m

Chicago Midway

Sat 8/8

6:47 pm-11:04 pm

1 stop3h 17m

$257

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/17

6:00 am-12:34 pm

1 stop7h 34m

Chicago Midway

Sat 9/19

9:30 am-5:20 pm

1 stop6h 50m

$259

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 9/22

4:05 pm-6:33 pm

1 stop3h 28m

Chicago Midway

Wed 9/30

9:30 am-5:20 pm

1 stop6h 50m

$260

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 6/23

12:14 pm-6:36 pm

1 stop7h 22m

Chicago Midway

Sat 6/27

9:22 am-3:24 pm

1 stop5h 02m

$269

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/8

6:00 am-12:33 pm

1 stop7h 33m

Chicago Midway

Tue 10/13

9:30 am-5:22 pm

1 stop6h 52m

$270
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 6/30

9:45 am-12:46 pm

1 stop4h 01m

Chicago Midway

Fri 7/3

9:17 am-3:19 pm

1 stop5h 02m

$275

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto Pearson Intl Airport, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, 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 $0.

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, Friday 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 $324.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $276 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $308. 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

Fastest flight time

3h 48m

Direct flights

None
The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 48m
There are no direct flights from Toronto Pearson Intl Airport to Chicago Midway Airport. There are no popular flight routes from Toronto Pearson Intl Airport to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Toronto Pearson Intl Airport to 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 48m 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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