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$ 270+ 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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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 5 November 2026.

Wed 25/116:00 a.m. -

1 stop4h 46m

Sun 29/119:30 a.m. -

1 stop3h 00m

Deal found 1/11C$ 455

Thu 26/116:00 a.m. -

1 stop6h 25m

Tue 1/121:41 p.m. -

1 stop8h 26m

Deal found 1/11C$ 459

Sat 14/116:00 a.m. -

1 stop4h 46m

Sun 15/119:30 a.m. -

1 stop3h 00m

Deal found 31/10C$ 462

Thu 26/116:00 a.m. -

1 stop6h 25m

Sun 29/119:30 a.m. -

1 stop3h 00m

Deal found 3/11C$ 466

Wed 16/126:00 a.m. -

1 stop8h 01m

Thu 7/19:38 a.m. -

1 stop8h 36m

Deal found 5/11C$ 493

Sat 28/116:00 a.m. -

1 stop7h 51m

Sun 29/111:31 p.m. -

1 stop8h 26m

Deal found 1/11C$ 501

Fri 27/116:00 a.m. -

1 stop6h 25m

Mon 30/119:30 a.m. -

1 stop6h 50m

Deal found 3/11C$ 507

Sat 14/116:00 a.m. -

1 stop4h 46m

Mon 16/111:31 p.m. -

1 stop8h 26m

Deal found 31/10C$ 512

Thu 26/116:04 a.m. -

1 stop6h 25m

Sun 29/111:35 p.m. -

1 stop8h 26m

Deal found 2/11C$ 518

Sat 28/1112:19 p.m. -

1 stop6h 49m

Tue 1/129:41 a.m. -

1 stop6h 43m

Deal found 4/11C$ 528

Find flight deals from Pearson Intl to Midway

Round-trip from	C$ 455
One-way from	C$ 270
Popular in	October
Cheapest in	February
Average price	C$ 402

Delta
25/11-29/11
2 total stops
7h 46m total
Toronto to Chicago

Search Deals

Delta
3/12-31/12
1 total stop
4h 37m total
Toronto to Chicago

Search Deals

Highest demand for flights based on searches. 2% potential increase in price (C$ 15 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in November 2026

Search Deals

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.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 5/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 4/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 6/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 11/1

6:10 a.m.-1:17 p.m.

1 stop8h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 17/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 1/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 9/1

6:10 a.m.-9:16 a.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 10/1

6:10 a.m.-9:16 a.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 272

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 19/1

12:10 p.m.-6:00 p.m.

1 stop6h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 272

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 17/1

6:10 a.m.-9:16 a.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 272

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/10

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

How often are flights from Toronto to Chicago delayed?

About 29% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 108 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 Sunday 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 49% of flights being delayed.

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 46m. 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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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$ 270

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/12. 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 5 November 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 5 November 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 5 November 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 5 November 2026.

Last-minute flights from Pearson Intl to MidwayDiscover last-minute flight deals from Pearson Intl to Midway. Data last updated 5 November 2026 and is based on user searches.

Discover last-minute flight deals from Pearson Intl to Midway. Data last updated 5 November 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 5 November 2026.

Search for one-way flight options from Pearson Intl to Midway. Find affordable one-way fares based on user searches. Data last updated 5 November 2026.

Find flight deals from Pearson Intl to Midway

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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.

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 often are flights from Toronto to Chicago delayed?

About 29% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 108 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 Sunday 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 49% 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

See prices for flight routes from nearby airports that may be better suited for you.

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

Book a non-stop flight to one of these other cities located in Illinois.

Search flights from Pearson Intl to Midway by cabin class

Find flights from Pearson Intl to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.

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 5 November 2026.

Pearson Intl and Midway flights

Browse other Pearson Intl and Midway flight options. Last updated on 5 November 2026.

Other flights from Pearson Intl

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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 5 November 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 5 November 2026.

Last-minute flights from Pearson Intl to Midway
Discover last-minute flight deals from Pearson Intl to Midway. Data last updated 5 November 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 5 November 2026.