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Cheap flights from Toronto Pearson Intl Airport to Chicago from $145

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 10/29. 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

WestJet Logo
6:20 am - 10:30 amYYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
$236WestJet
Find Deal
Sat, Oct 18 - Sat, Oct 25
Multiple Airlines Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
Multiple Airlines Logo
9:32 am - 8:00 pmMDW-YYZ
9h 28m1 stop
$253Multiple Airlines
Find Deal
Thu, Oct 16 - Fri, Oct 31
Multiple Airlines Logo
5:15 pm - 8:32 amYYZ-MDW
16h 17m1 stop
Multiple Airlines Logo
9:32 am - 2:05 pmMDW-YYZ
27h 33m1 stop
$254Multiple Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
WestJet Logo
6:20 am - 10:30 amYYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 am - 4:50 pmMDW-YYZ
5h 15m1 stop
$255WestJet
Find Deal
Sat, Oct 18 - Sat, Oct 25
Multiple Airlines Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
Multiple Airlines Logo
9:32 am - 8:00 pmMDW-YYZ
9h 28m1 stop
$256Multiple Airlines
Find Deal
Tue, Oct 21 - Fri, Oct 31
WestJet Logo
7:45 am - 10:14 pmYYZ-MDW
15h 29m1 stop
WestJet Logo
1:48 pm - 11:18 pmMDW-YYZ
8h 30m1 stop
$258WestJet
Find Deal
Mon, Oct 13 - Tue, Oct 21
WestJet Logo
6:00 pm - 9:45 amYYZ-MDW
16h 45m1 stop
WestJet Logo
10:40 am - 9:55 pmMDW-YYZ
10h 15m1 stop
$260WestJet
Find Deal
Wed, Oct 29 - Wed, Nov 5
WestJet Logo
6:00 pm - 9:45 amYYZ-MDW
16h 45m1 stop
WestJet Logo
10:40 am - 4:50 pmMDW-YYZ
5h 10m1 stop
$261WestJet
Find Deal
Wed, Oct 29 - Wed, Nov 5
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
WestJet Logo
12:48 pm - 9:55 pmMDW-YYZ
8h 07m1 stop
$262WestJet
Find Deal
Wed, Oct 15 - Tue, Oct 21
Delta Logo
12:15 pm - 6:25 pmYYZ-MDW
7h 10m1 stop
Delta Logo
9:35 am - 2:45 pmMDW-YYZ
4h 10m1 stop
$303Delta
Find Deal
Thu, Oct 23 - Wed, Oct 29

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
Oct 23
YYZ12:15 pmToronto Pearson Intl
7h 10m
1 stop
MDW6:25 pmChicago Midway
Oct 29
MDW9:35 amChicago Midway
4h 10m
1 stop
YYZ2:45 pmToronto Pearson Intl
$303
Find similar
Delta
Sep 25
YYZ6:00 amToronto Pearson Intl
8h 03m
1 stop
MDW1:03 pmChicago Midway
Sep 27
MDW6:15 pmChicago Midway
3h 41m
1 stop
YYZ10:56 pmToronto Pearson Intl
$474
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
Oct 18
YYZ6:20 amToronto Pearson Intl
5h 10m
1 stop
MDW10:30 amChicago Midway
Oct 25
MDW10:35 amChicago Midway
5h 15m
1 stop
YYZ4:50 pmToronto Pearson Intl
$236
Find similar
WestJet
Oct 18
YYZ6:20 amToronto Pearson Intl
5h 10m
1 stop
MDW10:30 amChicago Midway
Oct 25
MDW10:35 amChicago Midway
5h 15m
1 stop
YYZ4:50 pmToronto Pearson Intl
$255
Find similar
WestJet
Oct 13
YYZ7:45 amToronto Pearson Intl
15h 29m
1 stop
MDW10:14 pmChicago Midway
Oct 21
MDW1:48 pmChicago Midway
8h 30m
1 stop
YYZ11:18 pmToronto Pearson Intl
$258
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 September 16, 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 10/18

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

Sat 10/25

10:35 am-4:50 pm

1 stop5h 15m

$236

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/16

6:00 pm-10:14 pm

1 stop5h 14m

Chicago Midway

Fri 10/31

9:32 am-8:00 pm

1 stop9h 28m

$253

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/30

5:15 pm-8:32 am

1 stop16h 17m

Chicago Midway

Mon 11/3

9:32 am-2:05 pm

1 stop27h 33m

$254

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/18

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

Sat 10/25

10:35 am-4:50 pm

1 stop5h 15m

$255

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 10/21

6:00 pm-10:14 pm

1 stop5h 14m

Chicago Midway

Fri 10/31

9:32 am-8:00 pm

1 stop9h 28m

$256

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 10/13

7:45 am-10:14 pm

1 stop15h 29m

Chicago Midway

Tue 10/21

1:48 pm-11:18 pm

1 stop8h 30m

$258

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/29

6:00 pm-9:45 am

1 stop16h 45m

Chicago Midway

Wed 11/5

10:40 am-9:55 pm

1 stop10h 15m

$260

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/29

6:00 pm-9:45 am

1 stop16h 45m

Chicago Midway

Wed 11/5

10:40 am-4:50 pm

1 stop5h 10m

$261

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/15

6:00 pm-10:14 pm

1 stop5h 14m

Chicago Midway

Tue 10/21

12:48 pm-9:55 pm

1 stop8h 07m

$262

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/23

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

Wed 10/29

9:35 am-2:45 pm

1 stop4h 10m

$303

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, Saturday is the cheapest day to fly to Chicago Midway Airport from Toronto Pearson Intl Airport. The lowest ticket price found for a Saturday 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, 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 $289.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $120 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $270. 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

Direct flights

None
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

  • 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. 5h 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
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
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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