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

Over the past year, Porter Airlines has had the lowest number of delays on this route, with just 16% of flights being delayed.

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

Thursday 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.

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 in the early afternoon tend to experience delays more often.

How often are flights from Toronto to Chicago delayed?

About 16% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 107 minutes.

What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?

According to our current data, Porter Airlines (C$ 254), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 44% lower than the current average price of a flight leaving 3 months from now.

Weekly flight availability from Toronto Island Airport to Chicago Midway Airport

The most flights from YTZ to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

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 are the cheapest flights from Toronto Island Airport to Chicago Midway Airport?

On average you can expect to pay C$ 363 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 175 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 611.

What are the most reliable airlines from Toronto Island Airport to Chicago Midway Airport?

No one likes to see their flight delayed. When booking a flight from Toronto Island Airport to Chicago Midway Airport consider choosing Porter Airlines (72%), Porter Airlines (72%) or Air Transat (72%) as they are the most reliable in getting you off to your destination on time.

Can I find deals for flights from Toronto Island to Midway that include hotel bookings?

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

How can I find direct flights from Toronto Island to Midway?

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

Can I find deals for business class flights from Toronto Island to Midway?

Yes. Cheapflights offers flight deals from Toronto Island 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$ 274+ Cheap Flights from Toronto Island Airport to Chicago Midway Airport

Cheap flight deals from Toronto Island to Midway

Enter your travel dates to find the best prices.

Cheapest

Best

Direct

Last-minute

One-way

Cheapest flights from Toronto Island to Midway
Explore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 9 October 2026.

Mon 19/101:45 p.m. -

Nonstop1h 50m

Thu 22/103:20 p.m. -

Nonstop1h 40m

Deal found 5/10C$ 506

Tue 20/1010:10 a.m. -

Nonstop1h 50m

Wed 21/1011:45 a.m. -

Nonstop1h 40m

Deal found 5/10C$ 507

Tue 20/101:45 p.m. -

Nonstop1h 50m

Fri 23/103:20 p.m. -

Nonstop1h 40m

Deal found 5/10C$ 509

Wed 21/1010:10 a.m. -

Nonstop1h 50m

Sat 24/1011:45 a.m. -

Nonstop1h 40m

Deal found 7/10C$ 578

Fri 23/101:45 p.m. -

Nonstop1h 50m

Tue 27/106:42 p.m. -

2 stops41h 10m

Deal found 6/10C$ 596

Thu 22/101:45 p.m. -

Nonstop1h 50m

Sat 24/1011:45 a.m. -

Nonstop1h 40m

Deal found 7/10C$ 600

Fri 16/1010:10 a.m. -

Nonstop1h 50m

Mon 19/103:20 p.m. -

Nonstop1h 40m

Deal found 4/10C$ 611

Tue 13/101:45 p.m. -

Nonstop1h 50m

Tue 20/1011:45 a.m. -

Nonstop1h 40m

Deal found 5/10C$ 618

Sat 24/101:45 p.m. -

Nonstop1h 50m

Tue 27/109:53 a.m. -

2 stops25h 59m

Deal found 8/10C$ 633

Sun 18/1010:10 a.m. -

Nonstop1h 50m

Wed 21/103:20 p.m. -

Nonstop1h 40m

Deal found 5/10C$ 638

Wed 14/101:45 p.m. -

Nonstop1h 50m

Sun 18/1011:45 a.m. -

Nonstop1h 40m

Deal found 4/10C$ 641

Find flight deals from Toronto Island to Midway

Round-trip from	C$ 359
One-way from	C$ 274
Popular in	October
Cheapest in	January
Average price	C$ 781
Good round-trip deal	C$ 344 or less
Good one-way deal	C$ 186 or less

Porter Airlines
21/10-24/10
Nonstop
3h 30m total
Toronto to Chicago

Search Deals

Porter Airlines
21/10-31/12
Nonstop
1h 50m total
Toronto to Chicago

Search Deals

Highest demand for flights based on searches. 28% potential increase in price (C$ 259 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 7% potential price decrease (C$ 47 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2026

Search Deals

Price to beat on a round-trip flight from Toronto Island to Chicago Midway.

Search Deals

Price to beat on a one-way flight from Toronto Island to Chicago Midway.

Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 21/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 274

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 18/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 284

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 15/12

9:10 a.m.-11:33 a.m.

2 stops27h 23m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 299

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 23/11

4:15 p.m.-7:47 p.m.

2 stops28h 32m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 352

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 25/11

9:10 a.m.-8:14 a.m.

2 stops24h 04m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 365

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 30/3

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 368

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 16/11

4:15 p.m.-11:22 a.m.

3 stops20h 07m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 375

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 6/12

4:15 p.m.-8:42 p.m.

3 stops29h 27m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 392

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 14/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 395

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 20/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Tue 20/10

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 507

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 15 resultsSorted by cheapest first

Best time to book a flight from Toronto Island to Midway

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

YTZ-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 Island Airport to Chicago Midway Airport

Prices

Airlines

Delays

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

When flying from Toronto Island Airport to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 50% versus a flight in the evening.

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines from Toronto Island Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

468 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Porter Airlines

8.0

Very good

468 reviews

Porter Airlines

8.0

Very good

468 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

Related info for your journey

How long is the flight from Toronto Island Airport to Chicago Midway Airport?
For as low as C$ 507, Porter Airlines can have you in Chicago Midway Airport from Toronto Island Airport in 1h 50m. The distance from Toronto Island Airport to Chicago Midway Airport is about 711 km. Generally, flights for this route are direct.
What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?
According to our current data, Porter Airlines (C$ 254), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 44% lower than the current average price of a flight leaving 3 months from now.
What are the most reliable airlines from Toronto Island Airport to Chicago Midway Airport?
No one likes to see their flight delayed. When booking a flight from Toronto Island Airport to Chicago Midway Airport consider choosing Porter Airlines (72%), Porter Airlines (72%) or Air Transat (72%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Toronto Island Airport to Chicago Midway Airport?
On average you can expect to pay C$ 363 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 175 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 611.
Can I find deals for flights from Toronto Island to Midway that include hotel bookings?
Yes. In addition to deals on Toronto Island to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Toronto Island to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto Island to Midway.
Can I find deals for business class flights from Toronto Island to Midway?
Yes. Cheapflights offers flight deals from Toronto Island 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Complete your trip

Direct flights to Illinois

Flights by cabin class

Midway flight routes

Other flight options

Other flights from Toronto Island

Popular flights

Alternative routes for Toronto Island to Midway

Pearson Intl to O'Hare Intl flights

Pearson Intl to Midway flights

Toronto Island to O'Hare Intl flights

Hamilton to O'Hare Intl flights

Region of Waterloo Intl to O'Hare Intl flights

Top airline flying from Toronto Island to Midway

Airline	Cheapest	Average	Flexibility	On-time
Porter Airlines	CheapestC$ 254	AverageC$ 346	FlexibilityNo cancel fee	On-time52%	Search Porter Airlines flights

Fly with Cheapflights

How does Cheapflights help users find flights from Toronto Island to Midway?

Cheapflights makes it easy to find Toronto Island 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 Toronto Island 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 Toronto Island to Midway.

Can Cheapflights find flights from Toronto Island to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Toronto Island to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Toronto Island to Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 274

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 21/10. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Toronto Island to Midway

Cheapest flights from Toronto Island to MidwayExplore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 9 October 2026.

Explore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 9 October 2026.

Best flights from Toronto Island to MidwayDiscover carefully curated flight deals from Toronto Island to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 9 October 2026.

Discover carefully curated flight deals from Toronto Island to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 9 October 2026.

Direct flights from Toronto Island to MidwayExplore direct flight options from Toronto Island to Midway based on user searches, and compare prices and availability for your desired travel dates. Data last updated 9 October 2026.

Explore direct flight options from Toronto Island to Midway based on user searches, and compare prices and availability for your desired travel dates. Data last updated 9 October 2026.

Last-minute flights from Toronto Island to MidwayDiscover last-minute flight deals from Toronto Island to Midway. Data last updated 9 October 2026 and is based on user searches.

Discover last-minute flight deals from Toronto Island to Midway. Data last updated 9 October 2026 and is based on user searches.

One-way flights from Toronto Island to MidwaySearch for one-way flight options from Toronto Island to Midway. Find affordable one-way fares based on user searches. Data last updated 9 October 2026.

Search for one-way flight options from Toronto Island to Midway. Find affordable one-way fares based on user searches. Data last updated 9 October 2026.

Find flight deals from Toronto Island to Midway

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Cheapflights Fare Finder

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

Best time to book a flight from Toronto Island to Midway

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

Cheapflights Insights

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

When flying from Toronto Island Airport to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 50% versus a flight in the evening.

Weekly flight availability from Toronto Island Airport to Chicago Midway Airport

The most flights from YTZ to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

How often are flights from Toronto to Chicago delayed?

About 16% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 107 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 in the early afternoon tend to experience delays more often.

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

Thursday 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, Porter Airlines has had the lowest number of delays on this route, with just 16% of flights being delayed.

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines from Toronto Island Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?

What are the most reliable airlines from Toronto Island Airport to Chicago Midway Airport?

What are the cheapest flights from Toronto Island Airport to Chicago Midway Airport?

Can I find deals for flights from Toronto Island to Midway that include hotel bookings?

How can I find direct flights from Toronto Island to Midway?

Can I find deals for business class flights from Toronto Island to Midway?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Toronto Island 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 Toronto Island to Midway by cabin class

Find flights from Toronto Island 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 9 October 2026.

Toronto Island and Midway flights

Browse other Toronto Island and Midway flight options. Last updated on 9 October 2026.

Other flights from Toronto Island

Browse through other flights departing from Toronto Island. Flights are based on user searches made on Cheapflights and were last updated on 9 October 2026.

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Top airline flying from Toronto Island to Midway

Fly with Cheapflights

How does Cheapflights help users find flights from Toronto Island to Midway?

Why should you use Cheapflights to find cheap flight tickets from Toronto Island to Midway?

Can Cheapflights find flights from Toronto Island to Midway with no change fees?

Can Cheapflights notify me if prices for flights from Toronto Island to Midway become cheaper?

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Toronto Island to Midway
Explore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 9 October 2026.

Best flights from Toronto Island to Midway
Discover carefully curated flight deals from Toronto Island to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 9 October 2026.

Direct flights from Toronto Island to Midway
Explore direct flight options from Toronto Island to Midway based on user searches, and compare prices and availability for your desired travel dates. Data last updated 9 October 2026.

Last-minute flights from Toronto Island to Midway
Discover last-minute flight deals from Toronto Island to Midway. Data last updated 9 October 2026 and is based on user searches.

One-way flights from Toronto Island to Midway
Search for one-way flight options from Toronto Island to Midway. Find affordable one-way fares based on user searches. Data last updated 9 October 2026.