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Midway

$124+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$193
(Porter Airlines)

One-way from

$124
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$234

Good round-trip deal

$180 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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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. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 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 April 1, 2025.

This Porter Airlines deal was found by Cheapflights users on 4/1. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/127:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 5/219:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/1$193
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/249:30 amYTZ - MDW
Nonstop1h 50mAir Transat
Sun 4/275:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 4/1$209
This Trip.com deal was found by Cheapflights users on 3/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/259:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sun 4/275:35 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 3/31$217
This Delta deal was found by Cheapflights users on 4/1. 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.
Thu 5/13:59 pmYYZ - MDW
1 stop3h 21mDelta
Mon 5/53:02 pmMDW - YYZ
1 stop6h 53mDelta
Deal found 4/1$232
This FlightHub deal was found by Cheapflights users on 3/31. 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.
Thu 5/810:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Sun 5/119:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 3/31$239
This Delta deal was found by Cheapflights users on 4/1. 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.
Tue 4/297:00 amYUL - MDW
1 stop6h 03mDelta
Tue 5/612:48 pmMDW - YUL
1 stop10h 11mDelta
Deal found 4/1$274
This FlightHub deal was found by Cheapflights users on 3/31. 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.
Sat 5/248:00 pmYYZ - MDW
2 stops14h 40mWestJet
Tue 5/279:20 amMDW - YYZ
1 stop8h 11mWestJet
Deal found 3/31$291
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1210:15 amYYZ - MDW
1 stop13h 21mMultiple Airlines
Sun 4/1312:46 pmMDW - YYZ
1 stop24h 09mMultiple Airlines
Deal found 3/31$307
This Trip.com deal was found by Cheapflights users on 3/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2912:35 pmYOW - MDW
1 stop4h 49mPorter Airlines
Mon 6/29:40 amMDW - YOW
1 stop5h 53mPorter Airlines
Deal found 3/31$308
This FlightHub deal was found by Cheapflights users on 4/1. 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.
Tue 4/296:10 amYUL - MDW
1 stop9h 12mWestJet
Tue 5/612:48 pmMDW - YUL
1 stop21h 51mWestJet
Deal found 4/1$308
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/102:50 pmYUL - MDW
1 stop7h 24mMultiple Airlines
Mon 5/129:40 amMDW - YUL
1 stop5h 20mMultiple Airlines
Deal found 3/31$311
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Wed 4/162:50 pmYOW - MDW
2 stops15h 33mMultiple Airlines
Sat 4/1912:55 pmMDW - YOW
1 stop4h 24mMultiple Airlines
Deal found 4/1$379

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 April 1, 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

Mon 5/12

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Wed 5/21

9:40 am-12:22 pm

Nonstop1h 42m

$193

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/24

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sun 4/27

5:35 pm-8:17 pm

Nonstop1h 42m

$209

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/25

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sun 4/27

5:35 pm-8:17 pm

Nonstop1h 42m

$217

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/1

3:59 pm-6:20 pm

1 stop3h 21m

Chicago Midway

Mon 5/5

3:02 pm-10:55 pm

1 stop6h 53m

$232

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/8

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 5/11

9:40 am-4:00 pm

1 stop5h 20m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 4/29

7:00 am-12:03 pm

1 stop6h 03m

Chicago Midway

Tue 5/6

12:48 pm-11:59 pm

1 stop10h 11m

$274

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 5/24

8:00 pm-9:40 am

2 stops14h 40m

Chicago Midway

Tue 5/27

9:20 am-6:31 pm

1 stop8h 11m

$291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/12

10:15 am-10:36 pm

1 stop13h 21m

Chicago Midway

Sun 4/13

12:46 pm-1:55 pm

1 stop24h 09m

$307

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 4/29

6:10 am-2:22 pm

1 stop9h 12m

Chicago Midway

Tue 5/6

12:48 pm-11:39 am

1 stop21h 51m

$308

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 5/29

12:35 pm-4:24 pm

1 stop4h 49m

Chicago Midway

Mon 6/2

9:40 am-4:33 pm

1 stop5h 53m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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, 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 April 1, 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 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 1, 2025.
Read through reviews of airlines operating flights from Ontario to Chicago, such as Delta, Porter Airlines and Air Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,898 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
278 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 ($124), Air Transat ($132), and Delta ($156).

  • 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 Ontario?

Book flights to Ontario if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
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Québec City to O'Hare Intl flights
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Edmonton to Midway flights
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Halifax to Midway flights
St. John's to Midway flights
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Victoria to Midway flights
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Grande Prairie to O'Hare Intl flights
Medicine Hat to O'Hare Intl flights
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St John 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$347FlexibilityNo cancel feeOn-time52%

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