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Cheap flights from Ontario to Chicago Midway Airport from C$ 189

YYZ — MDW
3 Oct — 10 Oct1
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

Sun 27/910:10 a.m. -
Nonstop1h 50m
Wed 30/911:45 a.m. -
Nonstop1h 40m
Deal found 30/8C$ 299
Sat 17/101:45 p.m. -
Nonstop1h 50m
Sun 18/103:20 p.m. -
Nonstop1h 40m
Deal found 2/9C$ 301
Thu 24/910:10 a.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 31/8C$ 303
Sat 26/910:10 a.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 30/8C$ 306
Wed 30/910:10 a.m. -
Nonstop1h 50m
Fri 2/1011:45 a.m. -
Nonstop1h 40m
Deal found 2/9C$ 307
Mon 21/91:45 p.m. -
Nonstop1h 50m
Fri 25/93:20 p.m. -
Nonstop1h 40m
Deal found 1/9C$ 310
Sat 19/910:10 a.m. -
Nonstop1h 50m
Sun 20/911:45 a.m. -
Nonstop1h 40m
Deal found 29/8C$ 315
Tue 29/910:10 a.m. -
Nonstop1h 50m
Tue 6/1011:45 a.m. -
Nonstop1h 40m
Deal found 30/8C$ 317
Sat 19/910:10 a.m. -
Nonstop1h 50m
Wed 23/93:20 p.m. -
Nonstop1h 40m
Deal found 31/8C$ 318
Thu 24/96:00 a.m. -
1 stop4h 07m
Sun 27/99:29 a.m. -
1 stop6h 51m
Deal found 2/9C$ 318
Tue 22/91:45 p.m. -
Nonstop1h 50m
Tue 29/911:45 a.m. -
Nonstop1h 40m
Deal found 2/9C$ 319
Thu 24/96:00 a.m. -
1 stop4h 07m
Wed 30/99:29 a.m. -
1 stop6h 51m
Deal found 1/9C$ 319

Find flight deals from Ontario to Midway

Round-trip from

C$ 299

One-way from

C$ 189

Popular in

October

Cheapest in

February

Average price

C$ 360

Good round-trip deal

C$ 293 or less

Good one-way deal

C$ 286 or less
Air Transat
  • Air Transat
  • 27/9-30/9
  • Nonstop
  • 3h 30m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 25/9
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
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Highest demand for flights based on searches. 0% potential increase in price (C$ 1 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in September 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

Wed 30/9

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

Nonstop1h 50m

Chicago Midway

Fri 2/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 307

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 23/9

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

Nonstop1h 50m

Chicago Midway

Thu 24/9

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

Nonstop1h 40m

C$ 321

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 24/9

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Sun 27/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 340

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 28/9

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

Nonstop1h 50m

Chicago Midway

Mon 5/10

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

Nonstop1h 40m

C$ 356

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 12/10

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

Nonstop1h 50m

Chicago Midway

Fri 16/10

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

Nonstop1h 40m

C$ 381

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 19/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 23/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 383

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 25/11

6:00 a.m.-9:42 a.m.

1 stop4h 42m

Chicago Midway

Sun 17/1

9:30 a.m.-4:04 p.m.

1 stop5h 34m

C$ 387

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 8/10

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

1 stop7h 47m

Chicago Midway

Sun 11/10

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

1 stop6h 50m

C$ 401

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 29/9

9:45 a.m.-12:39 p.m.

1 stop3h 54m

Chicago Midway

Thu 1/10

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 401

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 15/9

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

Nonstop1h 50m

Chicago Midway

Fri 18/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 411

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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$ 283). Flying from Region of Ontario to Chicago Midway Airport in June is currently the most expensive (average of C$ 547). 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.

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

Airfare is below average for this route at the moment.
Region of Ontario to Chicago Midway Airport flights typically cost between C$ 419 and C$ 583 in September.
The cheapest round-trip price found within the last 5 days was C$ 318 on Delta (24 Sep-27 Sep).

Related info for your journey

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

    For as low as C$ 321, 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$ 283). Flying from Region of Ontario to Chicago Midway Airport in June is currently the most expensive (average of C$ 547). 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$ 220AverageC$ 339FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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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?

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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.

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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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