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Cheap flights from Ontario to Chicago Midway Airport from C$ 238

YYZ — MDW
4 Nov — 11 Nov1
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

Wed 21/101:45 p.m. -
Nonstop1h 50m
Sat 24/1011:45 a.m. -
Nonstop1h 40m
Deal found 4/10C$ 359
Fri 23/1010:10 a.m. -
Nonstop1h 50m
Fri 23/103:20 p.m. -
Nonstop1h 40m
Deal found 30/9C$ 427
Sat 17/1010:10 a.m. -
Nonstop1h 50m
Sat 24/103:20 p.m. -
Nonstop1h 40m
Deal found 2/10C$ 436
Wed 21/1010:10 a.m. -
Nonstop1h 50m
Thu 22/103:20 p.m. -
Nonstop1h 40m
Deal found 30/9C$ 440
Tue 20/101:45 p.m. -
Nonstop1h 50m
Fri 23/103:20 p.m. -
Nonstop1h 40m
Deal found 2/10C$ 452
Thu 22/101:45 p.m. -
Nonstop1h 50m
Sat 24/1011:45 a.m. -
Nonstop1h 40m
Deal found 3/10C$ 454
Sat 3/1010:10 a.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 1/10C$ 457
Sun 11/1010:10 a.m. -
Nonstop1h 50m
Sat 17/1011:45 a.m. -
Nonstop1h 40m
Deal found 3/10C$ 460
Thu 15/101:45 p.m. -
Nonstop1h 50m
Mon 19/103:20 p.m. -
Nonstop1h 40m
Deal found 1/10C$ 467
Mon 12/1010:10 a.m. -
Nonstop1h 50m
Fri 16/1011:45 a.m. -
Nonstop1h 40m
Deal found 3/10C$ 470
Sat 28/1112:15 p.m. -
1 stop6h 49m
Mon 7/126:41 p.m. -
1 stop3h 26m
Deal found 1/10C$ 470
Fri 23/1012:10 p.m. -
1 stop6h 50m
Fri 30/106:44 p.m. -
1 stop3h 12m
Deal found 2/10C$ 472

Find flight deals from Ontario to Midway

Round-trip from

C$ 359

One-way from

C$ 238

Popular in

October

Cheapest in

February

Average price

C$ 427

Good round-trip deal

C$ 344 or less

Good one-way deal

C$ 186 or less
Porter Airlines
  • Porter Airlines
  • 21/10-24/10
  • Nonstop
  • 3h 30m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 23/10-31/12
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
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Average for round-trip flights in October 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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Cheapflights Fare Finder

 
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 Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 23/10

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$ 239

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 22/10

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$ 239

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 31/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 24/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 14/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 11/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 18/11

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 20/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 12/11

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 8/11

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

1 stop7h 47m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/9

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

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$ 291). Flying from Region of Ontario to Chicago Midway Airport in October is currently the most expensive (average of C$ 671). 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?

It’s typically best to fly out from Region of Ontario to Chicago Midway Airport at noon. Doing so could potentially save you 50% on the flight price compared to flying in the evening, which is usually more expensive.

Related info for your journey

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

    For as low as C$ 359, 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 Montreal Pierre Elliott Trudeau Intl - Chicago Midway or Toronto Island - 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$ 291). Flying from Region of Ontario to Chicago Midway Airport in October is currently the most expensive (average of C$ 671). 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

Top airline flying from Ontario to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 254AverageC$ 346FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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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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