Cheap flights from Toronto to Chicago from $195

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
$331Delta
Thu, Dec 3 - Sun, Dec 6
Delta Logo
2:25 pm - 6:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 36m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:37 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 43m1 stop Detroit Metropolitan Wayne County
$331Delta
Mon, Dec 7 - Mon, Dec 14
Delta Logo
9:45 am - 1:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 16m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:33 am - 4:04 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
5h 31m1 stop Detroit Metropolitan Wayne County
$331Delta
Sun, Feb 7 - Sat, Feb 13
Delta Logo
12:15 pm - 6:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
$331Delta
Fri, Dec 4 - Mon, Dec 7
Delta Logo
9:45 am - 1:17 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 32m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:59 pm - 7:14 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 15m1 stop Detroit Metropolitan Wayne County
$331Delta
Fri, Jan 8 - Mon, Jan 11
Delta Logo
9:45 am - 1:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 16m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
$331Delta
Tue, Dec 1 - Fri, Dec 4
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
$332Delta
Thu, Dec 3 - Sun, Dec 6
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
$332Delta
Sat, Dec 5 - Mon, Dec 7
Delta Logo
6:00 am - 1:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
8h 01m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
$332Delta
Tue, Dec 1 - Wed, Dec 2
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 1:34 pmMDW  Chicago Midway-YTZ Toronto Island
24h 06m2 stops Atlanta Hartsfield-Jackson Newark
$485Multiple Airlines
Mon, Dec 7 - Wed, Dec 9

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Delta flights from Toronto to Chicago Midway Airport

Our best Delta deals on Toronto to Chicago Midway Airport flight tickets
Delta
Dec 3
YYZ6:00 amToronto Pearson Intl
4h 37m
1 stop
MDW9:37 amChicago Midway
Dec 6
MDW1:41 pmChicago Midway
8h 26m
1 stop
YYZ11:07 pmToronto Pearson Intl
$331
Delta
Dec 3
YYZ6:00 amToronto Pearson Intl
4h 37m
1 stop
MDW9:37 amChicago Midway
Dec 6
MDW1:41 pmChicago Midway
8h 26m
1 stop
YYZ11:07 pmToronto Pearson Intl
$332
Delta
Dec 10
YYZ9:45 amToronto Pearson Intl
4h 16m
1 stop
MDW1:01 pmChicago Midway
Dec 14
MDW1:41 pmChicago Midway
8h 26m
1 stop
YYZ11:07 pmToronto Pearson Intl
$336

WestJet flights from Toronto to Chicago Midway Airport

Our best WestJet deals on Toronto to Chicago Midway Airport flight tickets
WestJet
Nov 26
YYZ6:04 amToronto Pearson Intl
6h 25m
1 stop
MDW11:29 amChicago Midway
Nov 29
MDW1:35 pmChicago Midway
8h 26m
1 stop
YYZ11:01 pmToronto Pearson Intl
$379
WestJet
Feb 11
YYZ9:49 amToronto Pearson Intl
4h 16m
1 stop
MDW1:05 pmChicago Midway
Feb 14
MDW3:19 pmChicago Midway
6h 44m
1 stop
YYZ11:03 pmToronto Pearson Intl
$398
WestJet
Nov 27
YYZ6:04 amToronto Pearson Intl
6h 25m
1 stop
MDW11:29 amChicago Midway
Nov 29
MDW9:34 amChicago Midway
3h 00m
1 stop
YYZ1:34 pmToronto Pearson Intl
$411

momondo Fare Finder

 
Use the filters below to find and compare flights from Toronto 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

Thu 12/3

6:00 am-9:37 am

1 stop4h 37m

Chicago Midway

Sun 12/6

1:41 pm-11:07 pm

1 stop8h 26m

$331

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 12/7

2:25 pm-6:01 pm

1 stop4h 36m

Chicago Midway

Mon 12/14

9:37 am-5:20 pm

1 stop6h 43m

$331

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 2/7

9:45 am-1:01 pm

1 stop4h 16m

Chicago Midway

Sat 2/13

9:33 am-4:04 pm

1 stop5h 31m

$331

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 12/4

12:15 pm-6:01 pm

1 stop6h 46m

Chicago Midway

Mon 12/7

6:41 pm-11:07 pm

1 stop3h 26m

$331

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 1/8

9:45 am-1:17 pm

1 stop4h 32m

Chicago Midway

Mon 1/11

1:59 pm-7:14 pm

1 stop4h 15m

$331
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 12/1

9:45 am-1:01 pm

1 stop4h 16m

Chicago Midway

Fri 12/4

6:41 pm-11:07 pm

1 stop3h 26m

$331

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 12/3

6:00 am-9:37 am

1 stop4h 37m

Chicago Midway

Sun 12/6

1:41 pm-11:07 pm

1 stop8h 26m

$332

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 12/5

6:00 am-9:37 am

1 stop4h 37m

Chicago Midway

Mon 12/7

6:41 pm-11:07 pm

1 stop3h 26m

$332

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 12/1

6:00 am-1:01 pm

1 stop8h 01m

Chicago Midway

Wed 12/2

1:41 pm-11:07 pm

1 stop8h 26m

$332

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 12/7

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Wed 12/9

12:28 pm-1:34 pm

2 stops24h 06m

$485

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 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto, with most prices found around $204. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Toronto during the month December is also very affordable. Most momondo users find prices during this month for around $211.

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. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $344.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Toronto at noon is the least expensive time of day to depart. momondo users have found prices as low as $274 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $290. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Toronto to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago Midway flight prices

What cabin class options are available on Toronto to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Toronto to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Chicago Midway Airport flights?

You could potentially save up to 6% on your flight if you consider stops on a Toronto to Chicago Midway Airport flight.

When to book flights from Toronto to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto 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 to Chicago Midway Airport (YTO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago Midway Airport

Best Price Found

$195

Fastest flight time

3h 45m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is $195. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $331.
The fastest flight from Toronto to Chicago Midway Airport takes 3h 45m
There are no direct flights from Toronto to Chicago Midway Airport. There are no popular flight routes from Toronto to Chicago Midway Airport.

Frequently asked questions about flying from Toronto to Chicago Midway Airport

  • How far is Toronto to Chicago Midway by plane?

    There are 443.1 mi between Toronto and Chicago Midway. Typically, this will take 3h 45m by plane in normal conditions.

  • When did momondo last update prices for flights from Toronto to Chicago Midway Airport?

    Prices for flights from Toronto to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Toronto to Chicago Midway Airport?

  • How old do you have to be to fly from Toronto 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 to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Toronto to Chicago Midway Airport?

  • What is the most popular airline from Toronto to Chicago Midway Airport?

Best airlines flying from Toronto to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $185Free CancellationRating
8.0
468 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

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

momondo does allow users to show only those flights to Chicago from Toronto which offer a flexible booking policy as well as other useful filters and features.

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?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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1 adult
Tue 12/8
Tue 12/15

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