How often are flights from Toronto to Chicago delayed?

About 36% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 101 minutes.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the past year, Delta has had the lowest number of delays on this route, with just 57% of flights being delayed.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

What is the cheapest time of day to fly from YYZ to MDW?

When flying from Toronto Pearson Intl Airport to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Can I find deals for flights from Pearson Intl to Midway that include hotel bookings?

Yes. In addition to deals on Pearson Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Pearson Intl to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Midway.

Can I find deals for business class flights from Pearson Intl to Midway?

Yes. Cheapflights offers flight deals from Pearson Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

C$ 211+ Cheap Flights from Toronto Pearson Intl Airport to Chicago Midway Airport

Cheap flight deals from Pearson Intl to Midway

Enter your travel dates to find the best prices.

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Best

Last-minute

One-way

Cheapest flights from Pearson Intl to Midway
Explore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 August 2026.

Thu 10/912:08 p.m. -

1 stop5h 49m

Sun 13/96:40 p.m. -

1 stop3h 19m

Deal found 20/8C$ 330

Wed 9/96:00 a.m. -

1 stop4h 07m

Sat 12/95:37 p.m. -

1 stop4h 22m

Deal found 18/8C$ 341

Mon 7/96:15 a.m. -

1 stop7h 29m

Thu 10/99:34 a.m. -

1 stop6h 51m

Deal found 15/8C$ 361

Fri 11/99:50 a.m. -

1 stop7h 32m

Sun 13/96:45 p.m. -

1 stop3h 19m

Deal found 17/8C$ 363

Mon 7/99:45 a.m. -

1 stop3h 54m

Wed 9/95:37 p.m. -

1 stop4h 22m

Deal found 17/8C$ 373

Sat 5/912:09 p.m. -

1 stop5h 50m

Thu 10/99:29 a.m. -

1 stop6h 51m

Deal found 17/8C$ 384

Thu 24/96:00 a.m. -

1 stop4h 07m

Mon 28/99:29 a.m. -

1 stop6h 51m

Deal found 15/8C$ 397

Thu 10/99:45 a.m. -

1 stop8h 12m

Tue 15/99:29 a.m. -

1 stop6h 51m

Deal found 17/8C$ 399

Fri 4/96:10 a.m. -

1 stop4h 07m

Thu 10/99:29 a.m. -

1 stop6h 51m

Deal found 17/8C$ 402

Find flight deals from Pearson Intl to Midway

Round-trip from	C$ 339
One-way from	C$ 211
Popular in	April
Cheapest in	December
Average price	C$ 593

Delta
10/9-13/9
2 total stops
9h 08m total
Toronto to Chicago

Search Deals

Delta
9/9
1 total stop
5h 49m total
Toronto to Chicago

Search Deals

Highest demand for flights based on searches. 17% potential increase in price (C$ 136 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 6% potential price decrease (C$ 43 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in August 2026

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Cheapflights Fare Finder

Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 23/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Mon 28/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 339

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 21/9

12:08 p.m.-6:33 p.m.

1 stop7h 25m

Chicago Midway

Mon 28/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 339

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 26/9

12:08 p.m.-6:22 p.m.

1 stop7h 14m

Chicago Midway

Mon 28/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 339

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 11/9

9:45 a.m.-4:17 p.m.

1 stop7h 32m

Chicago Midway

Sun 13/9

6:40 p.m.-10:59 p.m.

1 stop3h 19m

C$ 341

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 12/9

9:45 a.m.-4:57 p.m.

1 stop8h 12m

Chicago Midway

Sat 26/9

9:29 a.m.-3:15 p.m.

1 stop4h 46m

C$ 341

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 23/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Sun 27/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 341

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 17/9

12:08 p.m.-6:33 p.m.

1 stop7h 25m

Chicago Midway

Tue 22/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 341

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 15/9

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Tue 22/9

9:29 a.m.-3:15 p.m.

1 stop4h 46m

C$ 341

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 30/9

12:08 p.m.-6:33 p.m.

1 stop7h 25m

Chicago Midway

Wed 7/10

9:29 a.m.-5:19 p.m.

1 stop6h 50m

C$ 407

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/9

12:08 p.m.-6:33 p.m.

1 stop7h 25m

Chicago Midway

Sun 27/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 461

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/8

Showing 1-10 of 21 resultsSorted by cheapest first

Best time to book a flight from Pearson Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pearson Intl with our price prediction graph.

YYZ-MDW

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago Midway Airport

Prices

Delays

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Toronto Pearson Intl Airport to Chicago Midway Airport flights typically cost between C$ 400 and C$ 701 in September.
The cheapest round-trip price found within the last 5 days was C$ 339 on Delta (10 Sep-13 Sep).

Related info for your journey

How long is the flight from Toronto Pearson Intl Airport to Chicago Midway Airport?
Airlines like Delta fly from Toronto Pearson Intl Airport to Chicago Midway Airport in about 4h 07m. The time it takes to get you to your destination can typically vary by up to . The distance from Toronto Pearson Intl Airport to Chicago Midway Airport is about 695 km.
Can I find deals for flights from Pearson Intl to Midway that include hotel bookings?
Yes. In addition to deals on Pearson Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Pearson Intl to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Midway.
Can I find deals for business class flights from Pearson Intl to Midway?
Yes. Cheapflights offers flight deals from Pearson Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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How does Cheapflights help users find flights from Pearson Intl to Midway?

Cheapflights makes it easy to find Pearson Intl to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Pearson Intl to Midway.

Can Cheapflights find flights from Pearson Intl to Midway with no change fees?

Yes, we can. To see specific flights from Pearson Intl to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Pearson Intl to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Pearson Intl today and book when prices fit your budget.

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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 211

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Pearson Intl to Midway

Cheapest flights from Pearson Intl to MidwayExplore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 August 2026.

Explore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 August 2026.

Best flights from Pearson Intl to MidwayDiscover carefully curated flight deals from Pearson Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 20 August 2026.

Discover carefully curated flight deals from Pearson Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 20 August 2026.

Last-minute flights from Pearson Intl to MidwayDiscover last-minute flight deals from Pearson Intl to Midway. Data last updated 20 August 2026 and is based on user searches.

Discover last-minute flight deals from Pearson Intl to Midway. Data last updated 20 August 2026 and is based on user searches.

One-way flights from Pearson Intl to MidwaySearch for one-way flight options from Pearson Intl to Midway. Find affordable one-way fares based on user searches. Data last updated 20 August 2026.

Search for one-way flight options from Pearson Intl to Midway. Find affordable one-way fares based on user searches. Data last updated 20 August 2026.

Find flight deals from Pearson Intl to Midway

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Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Best time to book a flight from Pearson Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pearson Intl with our price prediction graph.

Cheapflights Insights

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Toronto Pearson Intl Airport to Chicago Midway Airport flights typically cost between C$ 400 and C$ 701 in September.The cheapest round-trip price found within the last 5 days was C$ 339 on Delta (10 Sep-13 Sep).

How often are flights from Toronto to Chicago delayed?

About 36% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 101 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the past year, Delta has had the lowest number of delays on this route, with just 57% of flights being delayed.

Related info for your journey

How long is the flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

Can I find deals for flights from Pearson Intl to Midway that include hotel bookings?

How can I find direct flights from Pearson Intl to Midway?

Can I find deals for business class flights from Pearson Intl to Midway?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Pearson Intl to Midway

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Complete your trip

Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.

Direct flights to Illinois

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Other flights to Midway

Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 20 August 2026.

Pearson Intl and Midway flights

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How does Cheapflights help users find flights from Pearson Intl to Midway?

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Can Cheapflights find flights from Pearson Intl to Midway with no change fees?

Can Cheapflights notify me if prices for flights from Pearson Intl to Midway become cheaper?

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Cheapest flights from Pearson Intl to Midway
Explore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 August 2026.

Best flights from Pearson Intl to Midway
Discover carefully curated flight deals from Pearson Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 20 August 2026.

Last-minute flights from Pearson Intl to Midway
Discover last-minute flight deals from Pearson Intl to Midway. Data last updated 20 August 2026 and is based on user searches.

One-way flights from Pearson Intl to Midway
Search for one-way flight options from Pearson Intl to Midway. Find affordable one-way fares based on user searches. Data last updated 20 August 2026.

Toronto Pearson Intl Airport to Chicago Midway Airport flights typically cost between C$ 400 and C$ 701 in September.
The cheapest round-trip price found within the last 5 days was C$ 339 on Delta (10 Sep-13 Sep).