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Cheap flights from Ontario to Chicago Midway Airport from C$ 191

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 28/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
2 Sep — 9 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Ontario to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Ontario to Midway
Explore the most affordable flight options available from Ontario to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 August 2026.

Mon 31/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 2/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 29/7C$ 287
Tue 25/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Thu 27/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 31/7C$ 289
Fri 28/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 2/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/7C$ 290
Sat 29/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 8/911:45 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/7C$ 291
Tue 18/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 22/810:20 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/7C$ 293
Wed 19/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 24/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/8C$ 296
Tue 18/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 25/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/8C$ 297
Thu 20/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 24/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/8C$ 298
Sat 29/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 5/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 30/7C$ 300
Thu 20/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Sun 23/810:20 a.m.
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Deal found 30/7C$ 305
Thu 27/812:09 p.m.
YYZ
-
MDW
1 stop7h 24m
Delta
Sun 30/81:25 p.m.
MDW
-
YYZ
1 stop8h 38m
Delta
Deal found 3/8C$ 329
Thu 27/812:09 p.m.
YYZ
-
MDW
1 stop7h 24m
Air France
Sun 30/81:25 p.m.
MDW
-
YYZ
1 stop8h 38m
Air France
Deal found 3/8C$ 331

Find flight deals from Ontario to Midway

Keep the following information in mind while searching for Ontario to Midway flight deals. Data was last updated 3 August 2026.

Round-trip from

C$ 289

One-way from

C$ 191

Popular in

May

Cheapest in

September

Average price

C$ 387

Good round-trip deal

C$ 287 or less

Good one-way deal

C$ 181 or less
Porter Airlines
  • Porter Airlines
  • 28/8-2/9
  • Nonstop
  • 3h 30m total
  • Ontario to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 28/8
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Ontario to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Ontario to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Ontario to Midway 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, Cheapflights users made 629,999 searches. Data last updated 3 August 2026.
Use the filters below to find and compare flights from Ontario 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 - MDW

YTZMDW

Toronto Island

Tue 18/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 25/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 297

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/9

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

Nonstop1h 50m

Chicago Midway

Sun 13/9

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

Nonstop1h 40m

C$ 310

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/8

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

Nonstop1h 50m

Chicago Midway

Sat 29/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 311

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 30/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 3/9

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

Nonstop1h 40m

C$ 328

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 22/8

12:09 p.m.-6:33 p.m.

1 stop7h 24m

Chicago Midway

Sun 23/8

1:25 p.m.-11:03 p.m.

1 stop8h 38m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Tue 13/10

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

1 stop6h 50m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 15/10

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

1 stop6h 50m

Chicago Midway

Sun 18/10

6:44 p.m.-10:56 p.m.

1 stop3h 12m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 24/8

6:10 a.m.-12:39 p.m.

1 stop7h 29m

Chicago Midway

Thu 27/8

6:42 p.m.-11:03 p.m.

1 stop3h 21m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 31/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Wed 4/11

1:27 p.m.-10:56 p.m.

1 stop8h 29m

C$ 329

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Ontario to Midway

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

What is the cheapest month to book a flight from Region of Ontario to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 286). Flying from Region of Ontario to Chicago Midway Airport in June is currently the most expensive (average of C$ 552). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

Find hourly flight availability from Ontario to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 August 2026.

It’s typically best to fly out from Region of Ontario to Chicago Midway Airport at noon. Doing so could potentially save you 51% on the flight price compared to flying in the evening, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Ontario to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Region of Ontario to Chicago Midway Airport?

    For as low as C$ 297, Porter Airlines can have you in Chicago Midway Airport from Region of Ontario in 1h 50m. Airlines will cover a distance of 711 km. This flight may include one or multiple stops.

  • What are the most popular routes from Region of Ontario to Chicago Midway Airport?

    The most popular route from Region of Ontario to Chicago Midway Airport is Toronto Pearson Intl - Chicago Midway. You may also consider Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway.

  • Can I find deals for flights from Ontario to Midway that include hotel bookings?

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

  • How can I find direct flights from Ontario to Midway?

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

  • Can I find deals for business class flights from Ontario to Midway?

    Yes. Cheapflights offers flight deals from Ontario 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.

  • What is the cheapest month to book a flight from Region of Ontario to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 286). Flying from Region of Ontario to Chicago Midway Airport in June is currently the most expensive (average of C$ 552). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Ontario to Midway

Discover the top airline that operate flights from Ontario to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 200AverageC$ 331FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Ontario to Midway?

When you search for this flight from Ontario to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

Cheapflights simply makes it quick and affordable to book flights from Ontario to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

Certainly. Search results for flights to Midway from Ontario shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Of course! You can now track prices for flights from Ontario to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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