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Cheap flights from Toronto Pearson Intl Airport to Chicago 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 departing on 9/1. 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 Pearson Intl Airport to Chicago

Cheap round-trip flights

Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
6:15 pm - 10:56 pmMDW-YYZ
3h 41m1 stop
$212Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
$213Delta
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
10:12 am - 12:28 pmYYZ-MDW
3h 16m1 stop
Delta Logo
9:30 am - 1:32 pmMDW-YYZ
3h 02m1 stop
$224Delta
Find Deal
Sat, Aug 30 - Wed, Sep 10
Delta Logo
12:15 pm - 6:37 pmYYZ-MDW
7h 22m1 stop
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
$225Delta
Find Deal
Fri, Sep 5 - Tue, Sep 16
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
9:35 am - 3:22 pmMDW-YYZ
4h 47m1 stop
$236Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
6:30 am - 12:28 pmYYZ-MDW
6h 58m1 stop
Delta Logo
9:30 am - 5:23 pmMDW-YYZ
6h 53m1 stop
$237Delta
Find Deal
Wed, Aug 27 - Fri, Sep 5
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
9:29 am - 5:23 pmMDW-YYZ
6h 54m1 stop
$238Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
6:30 am - 8:35 amYYZ-MDW
3h 05m1 stop
Delta Logo
9:31 am - 1:32 pmMDW-YYZ
3h 01m1 stop
$239Delta
Find Deal
Thu, Sep 4 - Sun, Sep 7
WestJet Logo
1:20 pm - 9:26 pmYYZ-MDW
9h 06m1 stop
WestJet Logo
10:31 am - 4:57 pmMDW-YYZ
5h 26m1 stop
$280WestJet
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Thu, Sep 4 - Mon, Sep 8
WestJet Logo
1:20 pm - 10:14 pmYYZ-MDW
9h 54m1 stop
WestJet Logo
9:20 am - 6:12 amMDW-YYZ
19h 52m2 stops
$281WestJet
Find Deal
Fri, Oct 17 - Tue, Oct 21

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 13
YYZ12:14 pmToronto Pearson Intl
7h 21m
1 stop
MDW6:35 pmChicago Midway
Sep 20
MDW6:15 pmChicago Midway
3h 41m
1 stop
YYZ10:56 pmToronto Pearson Intl
$212
Find similar
Delta
Sep 25
YYZ12:14 pmToronto Pearson Intl
7h 21m
1 stop
MDW6:35 pmChicago Midway
Sep 29
MDW9:35 amChicago Midway
6h 48m
1 stop
YYZ5:23 pmToronto Pearson Intl
$213
Find similar
Delta
Aug 30
YYZ10:12 amToronto Pearson Intl
3h 16m
1 stop
MDW12:28 pmChicago Midway
Sep 10
MDW9:30 amChicago Midway
3h 02m
1 stop
YYZ1:32 pmToronto Pearson Intl
$224
Find similar

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
Sep 4
YYZ1:20 pmToronto Pearson Intl
9h 06m
1 stop
MDW9:26 pmChicago Midway
Sep 8
MDW10:31 amChicago Midway
5h 26m
1 stop
YYZ4:57 pmToronto Pearson Intl
$280
Find similar
WestJet
Oct 17
YYZ1:20 pmToronto Pearson Intl
9h 54m
1 stop
MDW10:14 pmChicago Midway
Oct 21
MDW9:20 amChicago Midway
19h 52m
2 stops
YYZ6:12 amToronto Pearson Intl
$281
Find similar
WestJet
Aug 19
YYZ7:45 amToronto Pearson Intl
14h 59m
1 stop
MDW9:44 pmChicago Midway
Aug 21
MDW12:43 pmChicago Midway
10h 16m
1 stop
YYZ11:59 pmToronto Pearson Intl
$282
Find similar

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 July 31, 2025.
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

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 9/13

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

Sat 9/20

6:15 pm-10:56 pm

1 stop3h 41m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/25

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

Mon 9/29

9:35 am-5:23 pm

1 stop6h 48m

$213

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 8/30

10:12 am-12:28 pm

1 stop3h 16m

Chicago Midway

Wed 9/10

9:30 am-1:32 pm

1 stop3h 02m

$224

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/5

12:15 pm-6:37 pm

1 stop7h 22m

Chicago Midway

Tue 9/16

9:35 am-5:23 pm

1 stop6h 48m

$225

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 9/23

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

Tue 9/30

9:35 am-3:22 pm

1 stop4h 47m

$236

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 8/27

6:30 am-12:28 pm

1 stop6h 58m

Chicago Midway

Fri 9/5

9:30 am-5:23 pm

1 stop6h 53m

$237

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/12

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

Fri 9/19

9:29 am-5:23 pm

1 stop6h 54m

$238

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/4

6:30 am-8:35 am

1 stop3h 05m

Chicago Midway

Sun 9/7

9:31 am-1:32 pm

1 stop3h 01m

$239

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/4

1:20 pm-9:26 pm

1 stop9h 06m

Chicago Midway

Mon 9/8

10:31 am-4:57 pm

1 stop5h 26m

$280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 10/17

1:20 pm-10:14 pm

1 stop9h 54m

Chicago Midway

Tue 10/21

9:20 am-6:12 am

2 stops19h 52m

$281

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 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, 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 $242. 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, Thursday 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 $279.

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 $244 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

$134

Fastest flight time

3h 05m

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 05m
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.
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  • 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 05m 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
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Benton Harbor
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Portage
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Crown Point
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Porter
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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.

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