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Cheap flights from Ontario to Chicago Midway Airport from C$ 165

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 28/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
14 Feb — 21 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Ontario to Midway

Keep the following information in mind while searching for Ontario to Midway flight deals. Data was last updated 15 January 2026.

Round-trip from

C$ 258

One-way from

C$ 165

Popular in

January

Cheapest in

July

Average price

C$ 402

Good round-trip deal

C$ 320 or less

Good one-way deal

C$ 199 or less
Air Transat
  • Air Transat
  • 6/2-8/2
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 28/1
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 60 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Ontario to Chicago Midway.
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Price to beat on a one-way flight from Ontario to Chicago Midway.
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Find 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 15 January 2026.

Fri 6/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Sun 8/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 14/1C$ 258
Fri 30/19:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 1/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 260
Thu 29/19:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 1/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 261
Tue 24/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Fri 27/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 13/1C$ 264
Thu 12/29:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 15/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 265
Mon 2/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 28/312:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 14/1C$ 267
Mon 2/29:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 7/212:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 268
Fri 20/26:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Mon 23/211:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 13/1C$ 268
Tue 27/19:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 30/111:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 270
Wed 1/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 7/44:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 271
Fri 17/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/44:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 272
Sun 5/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/44:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/1C$ 274

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 15 January 2026.
Use the filters below to find and compare flights from Ontario to Chicago Midway Airport that are best for you.

Fly from

Ontario

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 27/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 31/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/1

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

Nonstop1h 50m

Chicago Midway

Sun 1/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 260

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/1

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

Nonstop1h 50m

Chicago Midway

Mon 2/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 24/2

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

Nonstop1h 50m

Chicago Midway

Fri 27/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 264

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 267

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 267

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 12/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 268

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 11/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 268

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/1

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

Nonstop1h 50m

Chicago Midway

Sun 8/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/1

Showing 1-10 of 60 results
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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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 115). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of C$ 290). 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 15 January 2026.

It’s typically best to fly out from Region of Ontario to Chicago Midway Airport in the morning. Doing so could potentially save you 56% on the flight price compared to flying in the evening, which is usually more expensive.

How much does it cost to fly round-trip from Region of Ontario to Chicago Midway Airport?

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$ 258, 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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 115). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of C$ 290). 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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Alternative routes for Ontario to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Calgary to Midway flights
Hamilton to O'Hare Intl flights
Ottawa to Midway flights
Halifax to O'Hare Intl flights
Québec City to O'Hare Intl flights
Halifax to Midway flights
Edmonton to Midway flights
Québec City to Midway flights
Saskatoon to O'Hare Intl flights
Victoria to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Saskatoon to Midway flights
St John to O'Hare Intl flights
London to O'Hare Intl flights
Regina to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Kelowna to Midway flights
Victoria to Midway flights
Sudbury to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Moncton to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
St. John's to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Grande Prairie to Midway flights
Comox to O'Hare Intl flights
Kingston to O'Hare Intl flights
Deer Lake to O'Hare Intl flights

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 15 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 197AverageC$ 383FlexibilityNo 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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