Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 218

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 8/6. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
12:09 p.m. - 6:31 p.m.
YYZ
-
MDW
7h 22m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 364Delta
Thu, 11 Jun - Sun, 14 Jun
KLM Logo
2:29 p.m. - 6:31 p.m.
YYZ
-
MDW
5h 02m
1 stop
KLM Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 369KLM
Fri, 12 Jun - Tue, 16 Jun
Delta Logo
6:05 a.m. - 12:46 p.m.
YYZ
-
MDW
7h 41m
1 stop
Delta Logo
9:19 a.m. - 1:34 p.m.
MDW
-
YYZ
3h 15m
1 stop
C$ 376Delta
Thu, 25 Jun - Tue, 7 Jul
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
9:17 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 07m
1 stop
C$ 383Delta
Thu, 25 Jun - Wed, 1 Jul
Delta Logo
2:29 p.m. - 6:31 p.m.
YYZ
-
MDW
5h 02m
1 stop
Delta Logo
9:17 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 07m
1 stop
C$ 384Delta
Wed, 24 Jun - Tue, 30 Jun
WestJet Logo
6:10 a.m. - 9:19 a.m.
YYZ
-
MDW
4h 09m
1 stop
WestJet Logo
1:31 p.m. - 11:07 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 389WestJet
Sun, 14 Jun - Sun, 14 Jun
WestJet Logo
6:10 a.m. - 12:51 p.m.
YYZ
-
MDW
7h 41m
1 stop
WestJet Logo
9:22 a.m. - 3:24 p.m.
MDW
-
YYZ
5h 02m
1 stop
C$ 390WestJet
Sat, 20 Jun - Tue, 23 Jun
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
9:24 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 00m
1 stop
C$ 397Delta
Wed, 5 Aug - Sun, 9 Aug
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
9:17 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 07m
1 stop
C$ 398Delta
Thu, 18 Jun - Sun, 21 Jun
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
9:17 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 07m
1 stop
C$ 400Delta
Thu, 18 Jun - Mon, 22 Jun

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
11 Jun
YYZ12:09 p.m.Toronto Pearson Intl
7h 22m
1 stop
MDW6:31 p.m.Chicago Midway
14 Jun
MDW1:26 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:02 p.m.Toronto Pearson Intl
C$ 364
Delta
25 Jun
YYZ6:05 a.m.Toronto Pearson Intl
4h 09m
1 stop
MDW9:14 a.m.Chicago Midway
3 Jul
MDW9:17 a.m.Chicago Midway
7h 07m
1 stop
YYZ5:24 p.m.Toronto Pearson Intl
C$ 376
Delta
25 Jun
YYZ6:05 a.m.Toronto Pearson Intl
4h 09m
1 stop
MDW9:14 a.m.Chicago Midway
27 Jun
MDW5:47 p.m.Chicago Midway
4h 15m
1 stop
YYZ11:02 p.m.Toronto Pearson Intl
C$ 383

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
14 Jun
YYZ6:10 a.m.Toronto Pearson Intl
4h 09m
1 stop
MDW9:19 a.m.Chicago Midway
14 Jun
MDW1:31 p.m.Chicago Midway
8h 36m
1 stop
YYZ11:07 p.m.Toronto Pearson Intl
C$ 389
WestJet
20 Jun
YYZ6:10 a.m.Toronto Pearson Intl
7h 41m
1 stop
MDW12:51 p.m.Chicago Midway
23 Jun
MDW9:22 a.m.Chicago Midway
5h 02m
1 stop
YYZ3:24 p.m.Toronto Pearson Intl
C$ 390
WestJet
29 Jun
YYZ6:12 a.m.Toronto Pearson Intl
7h 41m
1 stop
MDW12:53 p.m.Chicago Midway
4 Jul
MDW9:24 a.m.Chicago Midway
3h 17m
1 stop
YYZ1:41 p.m.Toronto Pearson Intl
C$ 416

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 96,600 searches. Data last updated 29 May 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

Thu 11/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

Chicago Midway

Sun 14/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 364

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 12/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

Chicago Midway

Tue 16/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 369
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 25/6

6:05 a.m.-12:46 p.m.

1 stop7h 41m

Chicago Midway

Tue 7/7

9:19 a.m.-1:34 p.m.

1 stop3h 15m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 25/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Wed 1/7

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 383

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 24/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

Chicago Midway

Tue 30/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 384

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 14/6

6:10 a.m.-9:19 a.m.

1 stop4h 09m

Chicago Midway

Sun 14/6

1:31 p.m.-11:07 p.m.

1 stop8h 36m

C$ 389

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 20/6

6:10 a.m.-12:51 p.m.

1 stop7h 41m

Chicago Midway

Tue 23/6

9:22 a.m.-3:24 p.m.

1 stop5h 02m

C$ 390

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/8

6:10 a.m.-9:17 a.m.

1 stop4h 07m

Chicago Midway

Sun 9/8

9:24 a.m.-5:24 p.m.

1 stop7h 00m

C$ 397

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 18/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Sun 21/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 398

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 18/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Mon 22/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 400

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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?

In general, March is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 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 C$ 0.

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

The cheapest day to depart on your flight to Chicago Midway Airport is on a Friday when prices can be found for as low as C$ 294. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Toronto Pearson Intl Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 321.

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

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Toronto Pearson Intl Airport to Chicago Midway Airport during this time can be as low as C$ 296. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 670.

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 15m

Direct flights

None
The fastest flight from Toronto Pearson Intl Airport to Chicago Midway Airport takes 3h 15m
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 695.6 km. Flights usually cover this in 3h 15m, depending on flying conditions and air traffic around both airports.

  • 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 were last updated today.

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

  • How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto Pearson Intl Airport 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 airline from Toronto Pearson Intl Airport to Chicago Midway Airport?

Best airlines flying from Toronto Pearson Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 113Free CancellationRating
8.0
439 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

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?

Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 28/6
Sun 5/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago