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Cheap flights from Ontario to Chicago Midway Airport from C$ 148

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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 220

One-way from

C$ 148

Popular in

December

Cheapest in

April

Average price

C$ 346

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 26/6-29/6
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/7
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 40 potential increase over avg. RT price).
Search Deals
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 June 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 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 29/69:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/6C$ 220
Sat 30/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 12/99:15 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/6C$ 254
Mon 18/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 19/85:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 11/6C$ 280
Sat 4/1012:15 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/109:30 a.m.MDW - YYZ
1 stop6h 53mDelta
Deal found 11/6C$ 291
Fri 11/71:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 13/79:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 10/6C$ 309
Fri 3/107:00 a.m.YUL - MDW
1 stop10h 23mDelta
Wed 8/109:30 a.m.MDW - YUL
1 stop5h 30mDelta
Deal found 10/6C$ 324
Wed 30/78:35 a.m.YOW - MDW
1 stop8h 49mPorter Airlines
Tue 5/89:40 a.m.MDW - YOW
1 stop8h 13mPorter Airlines
Deal found 10/6C$ 357
Sat 11/107:00 a.m.YUL - MDW
1 stop15h 44mMultiple Airlines
Wed 15/109:15 a.m.MDW - YUL
1 stop8h 30mMultiple Airlines
Deal found 10/6C$ 436
Fri 25/75:55 a.m.YOW - MDW
1 stop11h 29mMultiple Airlines
Sun 27/79:40 a.m.MDW - YOW
1 stop8h 58mMultiple Airlines
Deal found 10/6C$ 447
Fri 3/106:15 p.m.YUL - MDW
1 stop28h 29mWestJet
Wed 8/101:05 p.m.MDW - YUL
2 stops10h 32mWestJet
Deal found 12/6C$ 487
Tue 22/76:30 p.m.YYZ - MDW
2 stops16h 15mWestJet
Tue 29/71:46 p.m.MDW - YYZ
2 stops15h 28mWestJet
Deal found 11/6C$ 494
Fri 27/65:55 a.m.YOW - MDW
2 stops16h 50mWestJet
Tue 1/712:44 p.m.MDW - YOW
2 stops10h 38mWestJet
Deal found 11/6C$ 813

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 12 June 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 26/6

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

Nonstop1h 50m

Chicago Midway

Sun 29/6

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

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

Nonstop1h 50m

Chicago Midway

Mon 30/6

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

Nonstop1h 40m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/8

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

Nonstop1h 50m

Chicago Midway

Tue 19/8

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

Nonstop1h 42m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 291

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 11/7

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Sun 13/7

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

1 stop5h 20m

C$ 309

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

7:00 a.m.-4:23 p.m.

1 stop10h 23m

Chicago Midway

Wed 8/10

9:30 a.m.-4:00 p.m.

1 stop5h 30m

C$ 324

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 30/7

8:35 a.m.-4:24 p.m.

1 stop8h 49m

Chicago Midway

Tue 5/8

9:40 a.m.-6:53 p.m.

1 stop8h 13m

C$ 357

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/10

7:00 a.m.-9:44 p.m.

1 stop15h 44m

Chicago Midway

Wed 15/10

9:15 a.m.-6:45 p.m.

1 stop8h 30m

C$ 436

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 25/7

5:55 a.m.-4:24 p.m.

1 stop11h 29m

Chicago Midway

Sun 27/7

9:40 a.m.-7:38 p.m.

1 stop8h 58m

C$ 447

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 17/7

1:04 p.m.-5:39 p.m.

1 stop5h 35m

Chicago Midway

Thu 24/7

6:20 p.m.-10:58 p.m.

1 stop3h 38m

C$ 483

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 33 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 12 June 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 12 June 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
288 reviews
Check prices

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
KLM
7.8
Good
1,358 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
396 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 148 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$ 156 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
Toronto Island to Midway flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Québec City to O'Hare Intl flights
Calgary to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Québec City to Midway flights
Calgary to Midway flights
Edmonton to Midway flights
Halifax to O'Hare Intl flights
Ottawa to Midway flights
St John to O'Hare Intl flights
Halifax to Midway flights
Saskatoon to O'Hare Intl flights
Moncton to O'Hare Intl flights
St. John's to O'Hare Intl flights
Victoria to O'Hare Intl flights
Regina to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Kelowna to Midway flights
Nanaimo to O'Hare Intl flights
Comox to O'Hare Intl flights
Saskatoon to Midway flights
Grande Prairie to O'Hare Intl flights
Grande Prairie to Midway flights
Fort McMurray to O'Hare Intl flights
London to O'Hare Intl flights
Victoria to Midway flights
Sudbury to O'Hare Intl flights
Kingston to O'Hare Intl flights
Deer Lake to O'Hare Intl 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 237AverageC$ 410FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 471AverageC$ 685FlexibilityNo cancel feeOn-time60%
Search WestJet 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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