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Cheap flights from Ontario to Chicago Midway Airport from C$ 270

YYZ — MDW
2 Dec — 9 Dec1
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 25/116:00 a.m. -
1 stop4h 46m
Sun 29/119:30 a.m. -
1 stop3h 00m
Deal found 1/11C$ 455
Thu 12/112:20 p.m. -
1 stop4h 44m
Mon 16/111:31 p.m. -
1 stop8h 26m
Deal found 28/10C$ 458
Thu 26/116:00 a.m. -
1 stop6h 25m
Sun 29/111:31 p.m. -
1 stop8h 26m
Deal found 1/11C$ 460
Tue 8/126:00 a.m. -
1 stop4h 37m
Wed 9/129:37 a.m. -
1 stop6h 43m
Deal found 30/10C$ 461
Sat 14/116:00 a.m. -
1 stop4h 46m
Sun 15/119:30 a.m. -
1 stop3h 00m
Deal found 31/10C$ 462
Tue 17/116:00 a.m. -
1 stop4h 46m
Tue 24/119:30 a.m. -
1 stop6h 50m
Deal found 30/10C$ 481
Sat 28/116:00 a.m. -
1 stop7h 51m
Sun 29/111:31 p.m. -
1 stop8h 26m
Deal found 1/11C$ 502
Fri 27/116:04 a.m. -
1 stop6h 25m
Sun 29/119:34 a.m. -
1 stop6h 50m
Deal found 1/11C$ 507
Sat 14/116:00 a.m. -
1 stop4h 46m
Mon 16/111:31 p.m. -
1 stop8h 26m
Deal found 31/10C$ 513
Thu 26/116:04 a.m. -
1 stop6h 25m
Sun 29/111:35 p.m. -
1 stop8h 26m
Deal found 2/11C$ 518
Tue 1/127:10 p.m. -
2 stops17h 23m
Tue 8/1212:28 p.m. -
2 stops20h 11m
Deal found 2/11C$ 664
Tue 1/127:10 p.m. -
2 stops17h 23m
Fri 4/125:02 p.m. -
2 stops19h 32m
Deal found 28/10C$ 692

Find flight deals from Ontario to Midway

Round-trip from

C$ 455

One-way from

C$ 270

Popular in

October

Cheapest in

February

Average price

C$ 402

Good round-trip deal

C$ 429 or less

Good one-way deal

C$ 320 or less
Delta
  • Delta
  • 25/11-29/11
  • 2 total stops
  • 7h 46m total
  • Ontario to Chicago
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Delta
  • Delta
  • 23/11-31/12
  • 1 total stop
  • 4h 46m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 15 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 November 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

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 23/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 5/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/12

12:20 p.m.-5:44 p.m.

1 stop6h 24m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 4/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 1/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 17/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 11/1

6:10 a.m.-1:17 p.m.

1 stop8h 07m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 9/1

6:10 a.m.-9:16 a.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 271

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 19/1

12:10 p.m.-6:00 p.m.

1 stop6h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 272

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 18/1

6:10 a.m.-1:01 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 272

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 57 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$ 285). Flying from Region of Ontario to Chicago Midway Airport in October is currently the most expensive (average of C$ 750). 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.

Related info for your journey

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

    For as low as C$ 458, Delta can have you in Chicago Midway Airport from Region of Ontario in 4h 44m. Airlines will cover a distance of 695 km.

  • 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$ 285). Flying from Region of Ontario to Chicago Midway Airport in October is currently the most expensive (average of C$ 750). 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$ 250AverageC$ 339FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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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