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Cheap flights from Toronto Pearson Intl Airport to Chicago from $147

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 9/19. 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
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
$236Delta
Sat, Sep 19 - Wed, Sep 30
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
$236Delta
Wed, Sep 16 - Tue, Sep 29
Delta Logo
12:08 pm - 6:33 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:40 pm - 10:59 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 19m1 stop Detroit Metropolitan Wayne County
$236Delta
Thu, Sep 17 - Sat, Sep 26
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
$236Delta
Wed, Sep 16 - Sat, Sep 26
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
$236Delta
Sat, Sep 19 - Sat, Sep 26
Delta Logo
9:45 am - 12:39 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
3h 54m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
$236Delta
Tue, Sep 15 - Wed, Sep 30
Delta Logo
12:08 pm - 6:22 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 14m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 3:15 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 46m1 stop Detroit Metropolitan Wayne County
$236Delta
Sat, Sep 19 - Tue, Sep 29
Delta Logo
6:00 am - 9:07 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
$236Delta
Sat, Sep 19 - Mon, Sep 28
Delta Logo
12:08 pm - 6:33 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 3:15 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 46m1 stop Detroit Metropolitan Wayne County
$236Delta
Mon, Sep 14 - Sat, Sep 26
Delta Logo
12:08 pm - 6:33 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 3:15 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 46m1 stop Detroit Metropolitan Wayne County
$236Delta
Thu, Sep 17 - Tue, Sep 29

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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 15
YYZ9:45 amToronto Pearson Intl
3h 54m
1 stop
MDW12:39 pmChicago Midway
Sep 30
MDW9:29 amChicago Midway
6h 51m
1 stop
YYZ5:20 pmToronto Pearson Intl
$236
Delta
Sep 21
YYZ6:00 amToronto Pearson Intl
4h 07m
1 stop
MDW9:07 amChicago Midway
Sep 27
MDW9:29 amChicago Midway
6h 51m
1 stop
YYZ5:20 pmToronto Pearson Intl
$244
Delta
Sep 6
YYZ12:09 pmToronto Pearson Intl
5h 50m
1 stop
MDW4:59 pmChicago Midway
Sep 13
MDW6:40 pmChicago Midway
3h 19m
1 stop
YYZ10:59 pmToronto Pearson Intl
$245

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 11
YYZ9:50 amToronto Pearson Intl
7h 32m
1 stop
MDW4:22 pmChicago Midway
Sep 19
MDW9:34 amChicago Midway
6h 51m
1 stop
YYZ5:25 pmToronto Pearson Intl
$259
WestJet
Sep 7
YYZ6:15 amToronto Pearson Intl
7h 29m
1 stop
MDW12:44 pmChicago Midway
Sep 14
MDW9:29 amChicago Midway
6h 56m
1 stop
YYZ5:25 pmToronto Pearson Intl
$260
WestJet
Dec 12
YYZ6:00 amToronto Pearson Intl
7h 35m
1 stop
MDW12:35 pmChicago Midway
Dec 14
MDW6:44 pmChicago Midway
3h 13m
1 stop
YYZ10:57 pmToronto Pearson Intl
$313

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 August 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 Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 9/19

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Wed 9/30

9:29 am-5:20 pm

1 stop6h 51m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 9/16

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Tue 9/29

9:29 am-5:20 pm

1 stop6h 51m

$236
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 9/17

12:08 pm-6:33 pm

1 stop7h 25m

Chicago Midway

Sat 9/26

6:40 pm-10:59 pm

1 stop3h 19m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 9/16

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Sat 9/26

9:29 am-5:20 pm

1 stop6h 51m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 9/19

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Sat 9/26

9:29 am-5:20 pm

1 stop6h 51m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 9/15

9:45 am-12:39 pm

1 stop3h 54m

Chicago Midway

Wed 9/30

9:29 am-5:20 pm

1 stop6h 51m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 9/19

12:08 pm-6:22 pm

1 stop7h 14m

Chicago Midway

Tue 9/29

9:29 am-3:15 pm

1 stop4h 46m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 9/19

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Mon 9/28

9:29 am-5:20 pm

1 stop6h 51m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 9/14

12:08 pm-6:33 pm

1 stop7h 25m

Chicago Midway

Sat 9/26

9:29 am-3:15 pm

1 stop4h 46m

$236

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 9/17

12:08 pm-6:33 pm

1 stop7h 25m

Chicago Midway

Tue 9/29

9:29 am-3:15 pm

1 stop4h 46m

$236

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 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, Tuesday is the cheapest day to fly to Chicago Midway Airport from Toronto Pearson Intl Airport. The lowest ticket price found for a Tuesday departure recently was $229. 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 $340.

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 $284 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $388. 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?

Book flights to Chicago if you plan to visit one of these locations
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Portage
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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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