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Cheap flights from Ontario to Chicago Midway Airport from C$ 144

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
8 Jul — 15 Jul1
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 3 July 2025.

Round-trip from

C$ 221

One-way from

C$ 144

Popular in

December

Cheapest in

April

Average price

C$ 343

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 154 or less
Porter Airlines
  • Porter Airlines
  • 15/7-15/7
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 12/9
  • Nonstop
  • 1h 49m 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).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in July 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 3 July 2025.

Fri 11/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 14/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 2/7C$ 221
Fri 5/97:30 a.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 8/99:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 1/7C$ 224
Wed 30/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Wed 6/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 1/7C$ 228
Mon 18/81:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 25/85:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 2/7C$ 292
Sat 4/1012:14 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/102:00 p.m.MDW - YYZ
1 stop7h 55mDelta
Deal found 1/7C$ 292
Fri 11/71:10 p.m.YUL - MDW
1 stop4h 14mMultiple Airlines
Mon 14/79:40 a.m.MDW - YUL
1 stop6h 40mMultiple Airlines
Deal found 2/7C$ 301
Tue 30/96:00 a.m.YUL - MDW
1 stop3h 40mDelta
Mon 6/101:05 p.m.MDW - YUL
1 stop9h 48mDelta
Deal found 2/7C$ 323
Fri 15/87:21 p.m.YYZ - MDW
1 stop18h 42mWestJet
Fri 22/812:43 p.m.MDW - YYZ
1 stop8h 15mWestJet
Deal found 2/7C$ 349
Fri 26/91:25 p.m.YOW - MDW
1 stop3h 59mPorter Airlines
Mon 29/99:15 a.m.MDW - YOW
1 stop6h 19mPorter Airlines
Deal found 1/7C$ 424
Mon 28/712:35 p.m.YOW - MDW
1 stop4h 49mMultiple Airlines
Tue 29/79:40 a.m.MDW - YOW
1 stop13h 42mMultiple Airlines
Deal found 3/7C$ 466
Fri 19/95:55 a.m.YOW - MDW
2 stops16h 41mWestJet
Mon 22/912:43 p.m.MDW - YOW
2 stops10h 39mWestJet
Deal found 2/7C$ 656
Wed 16/78:00 p.m.YXU - MDW
3 stops21h 24mMultiple Airlines
Fri 18/79:40 a.m.MDW - YXU
3 stops18h 34mMultiple Airlines
Deal found 1/7C$ 1,802

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 3 July 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

Tue 15/7

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

Nonstop1h 50m

Chicago Midway

Tue 15/7

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

Nonstop1h 42m

C$ 221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

Chicago Midway

Mon 8/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 30/7

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

Nonstop1h 50m

Chicago Midway

Wed 6/8

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

Nonstop1h 40m

C$ 228

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:14 p.m.-6:35 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

2:00 p.m.-10:55 p.m.

1 stop7h 55m

C$ 292

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 18/8

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

1 stop4h 14m

Chicago Midway

Mon 25/8

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 292

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 30/7

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

1 stop4h 14m

Chicago Midway

Wed 6/8

9:40 a.m.-7:20 p.m.

1 stop8h 40m

C$ 301

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 30/9

6:00 a.m.-8:40 a.m.

1 stop3h 40m

Chicago Midway

Mon 6/10

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

1 stop9h 48m

C$ 323

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 15/8

7:21 p.m.-1:03 p.m.

1 stop18h 42m

Chicago Midway

Fri 22/8

12:43 p.m.-9:58 p.m.

1 stop8h 15m

C$ 349

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 26/9

1:25 p.m.-4:24 p.m.

1 stop3h 59m

Chicago Midway

Mon 29/9

9:15 a.m.-4:34 p.m.

1 stop6h 19m

C$ 424

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 28/7

12:35 p.m.-4:24 p.m.

1 stop4h 49m

Chicago Midway

Tue 29/7

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

1 stop13h 42m

C$ 466

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 29 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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 238). 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 3 July 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.

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 3 July 2025.
Check out reviews from past customers who have flown with Porter Airlines,Delta, andAir Transat from Ontario to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Food

7.7

Crew

8.7

Comfort

8.1

Entertainment

7.0

Overall

8.0

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
298 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Food

7.7

Crew

8.7

Comfort

8.1

Entertainment

7.0

Overall

8.0

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
7,982 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Food

7.7

Crew

8.7

Comfort

8.1

Entertainment

7.0

Overall

8.0

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
407 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Food

7.7

Crew

8.7

Comfort

8.1

Entertainment

7.0

Overall

8.0

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
2,917 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Food

7.7

Crew

8.7

Comfort

8.1

Entertainment

7.0

Overall

8.0

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$ 144 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$ 147 and C$ 184, 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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 238). 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
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
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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 3 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 230AverageC$ 393FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 470AverageC$ 668FlexibilityNo 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?

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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