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Midway

$103+ Cheap flights from Ontario to Midway (MDW)

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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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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 July 31, 2025.

Round-trip from

$149
(SmartFares)

One-way from

$103
(SmartFares)

Popular in

December

Cheapest in

June

Average price

$270

Good round-trip deal

$170 or less

Good one-way deal

$101 or less
From Ontario to Chicago Midway
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One-way flight from Ontario to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 July 31, 2025.

This SmartFares deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 9/225:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/29$149
This Cheapflightsfares deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/19:00 amYTZ - MDW
Nonstop1h 50mAir Transat
Wed 9/39:35 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 7/29$166
This Mytrip deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 9/295:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 7/29$196
This Flightnetwork deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/310:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Sun 10/55:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 7/29$198
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1312:14 pmYYZ - MDW
1 stop7h 21mDelta
Sat 9/201:43 pmMDW - YYZ
1 stop8h 37mDelta
Deal found 7/29$212
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:00 amYUL - MDW
1 stop3h 35mDelta
Sat 9/66:00 amMDW - YUL
1 stop6h 38mDelta
Deal found 7/30$215
This FlightHub deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:52 amYYZ - MDW
1 stop11h 22mWestJet
Tue 10/2112:48 pmMDW - YYZ
1 stop8h 07mWestJet
Deal found 7/31$268
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2112:35 pmYOW - MDW
1 stop4h 49mPorter Airlines
Tue 8/269:40 amMDW - YOW
1 stop6h 23mPorter Airlines
Deal found 7/28$324
This Mytrip deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/285:55 amYOW - MDW
1 stop11h 29mMultiple Airlines
Thu 9/49:35 amMDW - YOW
1 stop13h 47mMultiple Airlines
Deal found 7/29$355
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/35:55 amYOW - MDW
2 stops12h 42mWestJet
Sun 9/79:15 amMDW - YOW
2 stops14h 07mWestJet
Deal found 7/31$468
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/35:55 amYOW - MDW
2 stops7h 33mDelta
Sun 9/79:31 amMDW - YOW
2 stops13h 51mDelta
Deal found 7/30$718
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/158:00 pmYXU - MDW
2 stops14h 36mWestJet
Mon 8/1812:43 pmMDW - YXU
2 stops29h 26mWestJet
Deal found 7/30$1,010

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 2,558,603 searches. Data last updated July 31, 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 9/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Mon 9/22

5:20 pm-8:02 pm

Nonstop1h 42m

$149

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 9/1

9:00 am-9:50 am

Nonstop1h 50m

Chicago Midway

Wed 9/3

9:35 am-12:17 pm

Nonstop1h 42m

$166

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/25

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 9/29

5:20 pm-8:02 pm

Nonstop1h 42m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/3

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 10/5

5:20 pm-10:15 pm

1 stop3h 55m

$198

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 9/13

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

Sat 9/20

6:15 pm-10:56 pm

1 stop3h 41m

$212

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Sat 9/6

6:00 am-1:38 pm

1 stop6h 38m

$215

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 10/17

11:52 am-10:14 pm

1 stop11h 22m

Chicago Midway

Tue 10/21

12:48 pm-9:55 pm

1 stop8h 07m

$268

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 8/21

12:35 pm-4:24 pm

1 stop4h 49m

Chicago Midway

Tue 8/26

9:40 am-5:03 pm

1 stop6h 23m

$324

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 8/28

5:55 am-4:24 pm

1 stop11h 29m

Chicago Midway

Thu 9/4

9:35 am-12:22 am

1 stop13h 47m

$355

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 9/3

5:55 am-5:37 pm

2 stops12h 42m

Chicago Midway

Sun 9/7

9:15 am-12:22 am

2 stops14h 07m

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of $160). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 July 31, 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 July 31, 2025.
Read through reviews of airlines operating flights from Ontario to Chicago Midway Airport, such as Porter Airlines, Delta, and Air Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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?

    The cheapest airlines for a one-way flight from Region of Ontario to Chicago Midway Airport are Porter Airlines ($103), Air Transat ($106), and Delta ($134).

  • What are the most popular routes from Region of Ontario to Chicago Midway Airport?

    When deciding which route to take from Region of Ontario to Chicago Midway Airport consider Toronto Island - Chicago Midway, Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway as they are the most popular.

  • 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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of $160). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Québec City to O'Hare Intl flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Calgary to Midway flights
Abbotsford to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Québec City to Midway flights
Winnipeg to Midway flights
Edmonton to Midway flights
Ottawa to Midway flights
Halifax to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Halifax to Midway flights
Victoria to O'Hare Intl flights
Victoria to Midway flights
Hamilton to O'Hare Intl flights
Moncton to O'Hare Intl flights
London to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Regina to O'Hare Intl flights
Kelowna to O'Hare Intl flights
London to Midway flights
St. John's to Midway flights
St John to O'Hare Intl flights
Comox to O'Hare Intl flights
Medicine Hat to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights

Top airline flying from Ontario to Midway

Discover the top airline 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 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$257FlexibilityNo cancel feeOn-time52%

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