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Cheap flights from Ontario to Chicago Midway Airport from C$ 144

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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
5 Sep — 12 Sep1
1 adult

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 31 August 2025.

Round-trip from

C$ 238

One-way from

C$ 144

Popular in

December

Cheapest in

July

Average price

C$ 386

Good round-trip deal

C$ 239 or less

Good one-way deal

C$ 203 or less
Porter Airlines
  • Porter Airlines
  • 21/9-26/9
  • Nonstop
  • 3h 31m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 7/10
  • Nonstop
  • 1h 49m total
  • Ontario to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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

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 31 August 2025.

Sun 21/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 26/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 30/8C$ 238
Thu 2/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 30/8C$ 242
Tue 23/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 31/8C$ 245
Fri 3/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 30/8C$ 249
Thu 30/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 5/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/8C$ 251
Wed 1/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 4/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 30/8C$ 253
Fri 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 19/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 30/8C$ 254
Thu 30/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 8/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/8C$ 256
Wed 1/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 30/8C$ 257
Mon 20/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sat 1/116:35 p.m.MDW - YYZ
1 stop3h 20mDelta
Deal found 31/8C$ 293
Mon 10/116:00 a.m.YUL - MDW
1 stop7h 34mDelta
Tue 18/1110:47 a.m.MDW - YUL
1 stop5h 34mDelta
Deal found 29/8C$ 297
Thu 2/106:30 a.m.YYZ - MDW
1 stop6h 58mDelta
Sun 5/109:35 a.m.MDW - YYZ
1 stop6h 48mDelta
Deal found 29/8C$ 309

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 31 August 2025.
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

Sun 21/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Fri 26/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 19/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 5/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 27/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 29/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 6/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 16/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 23/11

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

Nonstop1h 42m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Wed 22/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 247

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 14/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Tue 21/10

9:35 a.m.-2:45 p.m.

1 stop4h 10m

C$ 293

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 22/10

6:15 a.m.-12:28 p.m.

1 stop7h 13m

Chicago Midway

Sat 1/11

11:10 a.m.-5:19 p.m.

1 stop5h 09m

C$ 293

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 1/11

6:15 a.m.-8:40 a.m.

1 stop3h 25m

Chicago Midway

Sun 2/11

9:35 a.m.-5:19 p.m.

1 stop6h 44m

C$ 293

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/8

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, September is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 221). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 31 August 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Region of Ontario to Chicago Midway Airport as you normally would.

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$ 238, Porter Airlines can have you in Chicago Midway Airport from Region of Ontario in 1h 49m. 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, September is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 221). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.
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Pearson Intl to Midway flights
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Ottawa to Midway flights
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Victoria to Midway flights
Victoria to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Saskatoon to Midway flights
Regina to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
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Comox to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
St John to O'Hare Intl flights
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St. John's to O'Hare Intl flights
Kingston to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Grande Prairie to Midway flights
Moncton to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Kelowna to Midway flights

Top 2 airlines flying from Ontario to Midway

Discover the top 2 airlines 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 31 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 204AverageC$ 396FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 418AverageC$ 599FlexibilityNo cancel feeOn-time60%
Search WestJet 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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