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Cheap flights from Ontario to Chicago Midway Airport from C$ 163

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
27 Apr — 4 May1
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 22 April 2025.

Round-trip from

C$ 269

One-way from

C$ 163

Popular in

December

Cheapest in

March

Average price

C$ 348

Good round-trip deal

C$ 266 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 8/5-8/5
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 6/6
  • 1 total stop
  • 4h 44m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 27 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 April 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 22 April 2025.

Thu 8/57:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 8/55:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/4C$ 269
Fri 6/69:49 a.m.YYZ - MDW
1 stop3h 39mDelta
Sat 7/65:25 p.m.MDW - YYZ
1 stop4h 33mDelta
Deal found 21/4C$ 293
Sun 13/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 16/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 21/4C$ 309
Fri 30/51:10 p.m.YUL - MDW
1 stop4h 44mPorter Airlines
Mon 2/69:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 21/4C$ 318
Fri 9/512:15 p.m.YYZ - MDW
1 stop7h 30mKLM
Sun 11/56:25 p.m.MDW - YYZ
1 stop3h 33mKLM
Deal found 21/4C$ 325
Fri 6/67:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Sun 8/65:50 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 20/4C$ 334
Sat 6/97:30 a.m.YUL - MDW
1 stop6h 32mDelta
Sat 13/91:05 p.m.MDW - YUL
1 stop9h 48mDelta
Deal found 21/4C$ 334
Thu 22/510:45 a.m.YUL - MDW
1 stop6h 39mMultiple Airlines
Sat 24/59:40 a.m.MDW - YUL
1 stop13h 57mMultiple Airlines
Deal found 21/4C$ 366
Fri 18/710:15 a.m.YOW - MDW
1 stop7h 09mPorter Airlines
Mon 21/79:40 a.m.MDW - YOW
1 stop5h 53mPorter Airlines
Deal found 21/4C$ 367
Sat 17/511:30 a.m.YYZ - MDW
1 stop10h 44mWestJet
Sat 31/512:48 p.m.MDW - YYZ
1 stop10h 07mWestJet
Deal found 21/4C$ 420
Wed 21/56:15 a.m.YUL - MDW
1 stop12h 30mWestJet
Sun 25/59:20 a.m.MDW - YUL
2 stops20h 48mWestJet
Deal found 21/4C$ 488
Tue 29/46:10 p.m.YYZ - MDW
1 stop5h 12mMultiple Airlines
Sat 3/510:48 a.m.MDW - YYZ
2 stops23h 47mMultiple Airlines
Deal found 20/4C$ 624

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 22 April 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

Thu 8/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 8/5

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

Nonstop1h 42m

C$ 269

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 6/6

9:49 a.m.-12:28 p.m.

1 stop3h 39m

Chicago Midway

Sat 7/6

5:25 p.m.-10:58 p.m.

1 stop4h 33m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 13/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sat 16/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 309

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 30/5

1:10 p.m.-4:54 p.m.

1 stop4h 44m

Chicago Midway

Mon 2/6

9:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 318

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/5

12:15 p.m.-6:45 p.m.

1 stop7h 30m

Chicago Midway

Sun 11/5

6:25 p.m.-10:58 p.m.

1 stop3h 33m

C$ 325

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 334

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 6/9

7:30 a.m.-1:02 p.m.

1 stop6h 32m

Chicago Midway

Sat 13/9

1:05 p.m.-11:53 p.m.

1 stop9h 48m

C$ 334

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/5

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sat 24/5

9:40 a.m.-12:37 a.m.

1 stop13h 57m

C$ 366

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 18/7

10:15 a.m.-4:24 p.m.

1 stop7h 09m

Chicago Midway

Mon 21/7

9:40 a.m.-4:33 p.m.

1 stop5h 53m

C$ 367

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 21/5

12:30 p.m.-5:45 p.m.

1 stop6h 15m

Chicago Midway

Wed 28/5

12:48 p.m.-9:56 p.m.

1 stop8h 08m

C$ 391

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/4

Showing 1-10 of 32 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, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 243). 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 22 April 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 22 April 2025.
To help decide which airline to fly from Ontario to Chicago, see what other customers have to say about Porter Airlines, Delta and KLM. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
284 reviews
Check prices

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
284 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,920 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
KLM
7.8
Good
1,331 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,813 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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.

  • What are the cheapest airlines to fly from Region of Ontario to Chicago Midway Airport one-way?

    C$ 163 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on Air Transat and Delta, with prices starting from C$ 178 and C$ 185, respectively.

  • 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, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 243). 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

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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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Québec City to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Québec City to Midway flights
Edmonton to O'Hare Intl flights
Vancouver Intl to Midway flights
Calgary to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Edmonton to Midway flights
Hamilton to O'Hare Intl flights
Ottawa to Midway flights
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Halifax to Midway flights
St. John's to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
St John to O'Hare Intl flights
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Nanaimo to O'Hare Intl flights
London to O'Hare Intl flights
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Victoria to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Deer Lake to O'Hare Intl flights
Comox to O'Hare Intl flights
Victoria to Midway flights
Saskatoon to Midway flights
Saskatoon to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Kelowna to Midway flights
Kingston to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Grande Prairie 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 22 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 260AverageC$ 425FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 476AverageC$ 650FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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?

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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.

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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