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Cheap flights from Ontario to Chicago Midway Airport from C$ 142

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
8 Apr — 15 Apr1
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 9 March 2026.

Thu 30/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Mon 4/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 4/3C$ 214
Sun 19/49:50 a.m.
YUL
-
MDW
1 stop6h 30m
Porter Airlines
Thu 23/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 5/3C$ 216
Fri 17/411:45 a.m.
YUL
-
MDW
1 stop4h 35m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 5/3C$ 231
Thu 7/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 10/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 4/3C$ 232
Fri 17/411:45 a.m.
YUL
-
MDW
1 stop4h 35m
Porter Airlines
Tue 21/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 5/3C$ 235
Fri 10/411:45 a.m.
YUL
-
MDW
1 stop4h 35m
Porter Airlines
Mon 13/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 4/3C$ 236
Fri 1/510:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 3/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 7/3C$ 246
Fri 1/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Wed 6/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 4/3C$ 248
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 10/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 7/3C$ 250
Fri 19/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Mon 22/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 5/3C$ 258
Sat 4/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 11/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 6/3C$ 260
Thu 16/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 8/3C$ 262

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 9 March 2026.

Round-trip from

C$ 214

One-way from

C$ 142

Popular in

December

Cheapest in

July

Average price

C$ 358

Good round-trip deal

C$ 254 or less
Porter Airlines
  • Porter Airlines
  • 30/4-4/5
  • 2 total stops
  • 10h 15m total
  • Ontario to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/5
  • 1 total stop
  • 4h 10m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip 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 9 March 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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Mon 20/4

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

Nonstop1h 42m

C$ 262
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 27/5

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

Nonstop1h 50m

Chicago Midway

Fri 29/5

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

Nonstop1h 40m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Tue 14/4

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

Nonstop1h 42m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 23/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Sun 26/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Sun 19/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

C$ 285

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 27/5

7:00 a.m.-4:12 p.m.

1 stop10h 12m

Chicago Midway

Sun 31/5

6:36 p.m.-11:13 p.m.

1 stop3h 37m

C$ 321

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 18/4

6:10 a.m.-12:43 p.m.

1 stop7h 33m

Chicago Midway

Sat 25/4

6:38 p.m.-10:56 p.m.

1 stop3h 18m

C$ 326

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 19/4

6:30 a.m.-1:32 p.m.

1 stop8h 02m

Chicago Midway

Sun 26/4

9:27 a.m.-5:21 p.m.

1 stop6h 54m

C$ 326

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 6/5

12:22 p.m.-6:36 p.m.

1 stop7h 14m

Chicago Midway

Wed 13/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

C$ 326

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 24/4

6:10 a.m.-12:43 p.m.

1 stop7h 33m

Chicago Midway

Mon 27/4

6:38 p.m.-10:56 p.m.

1 stop3h 18m

C$ 326

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 113). Flying from Region of Ontario to Chicago Midway Airport in February is currently the most expensive (average of C$ 383). 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 9 March 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 57% 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$ 262, 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 Island - Chicago Midway. You may also consider Toronto Pearson Intl - 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$ 113). Flying from Region of Ontario to Chicago Midway Airport in February is currently the most expensive (average of C$ 383). 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 9 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 111AverageC$ 378FlexibilityNo 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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