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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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$176
(Cheapflightsfares)

One-way from

$124
(FlightHub)

Popular in

December

Cheapest in

March

Average price

$261

Good round-trip deal

$192 or less

Good one-way deal

$115 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. 5% potential increase in price ($15 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 5/289:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/30$176
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/127:55 amYTZ - MDW
Nonstop1h 50mAir Transat
Sun 6/159:40 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 4/29$186
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/214:05 pmYTZ - MDW
Nonstop1h 49mMultiple Airlines
Sun 5/255:50 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 4/29$206
This Trip.com deal was found by Cheapflights users on 4/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/310:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Tue 6/109:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 4/30$229
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/53:50 pmYYZ - MDW
1 stop3h 55mDelta
Tue 6/109:24 amMDW - YYZ
1 stop6h 51mDelta
Deal found 4/30$260
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/226:15 amYUL - MDW
1 stop8h 00mDelta
Mon 5/269:16 amMDW - YUL
1 stop5h 59mDelta
Deal found 4/30$278
This flugladen.de deal was found by Cheapflights users on 4/30. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3012:30 pmYYZ - MDW
1 stop6h 15mWestJet
Fri 6/69:20 amMDW - YYZ
1 stop8h 11mWestJet
Deal found 4/30$301
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/612:35 pmYOW - MDW
1 stop5h 19mPorter Airlines
Sun 6/229:40 amMDW - YOW
1 stop5h 53mPorter Airlines
Deal found 4/30$307
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/55:55 amYOW - MDW
1 stop11h 29mMultiple Airlines
Sun 6/89:40 amMDW - YOW
1 stop13h 42mMultiple Airlines
Deal found 4/30$322
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:00 amYUL - MDW
2 stops15h 13mMultiple Airlines
Mon 5/269:40 amMDW - YUL
1 stop5h 20mMultiple Airlines
Deal found 4/30$338
This FlightHub deal was found by Cheapflights users on 5/1. 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.
Thu 5/156:15 amYUL - MDW
1 stop12h 30mWestJet
Wed 5/2112:48 pmMDW - YUL
1 stop27h 52mWestJet
Deal found 5/1$369
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/58:00 pmYYZ - MDW
2 stops14h 40mMultiple Airlines
Sun 6/89:12 pmMDW - YYZ
1 stop15h 43mMultiple Airlines
Deal found 4/30$414

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 May 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

Sat 5/24

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Wed 5/28

9:40 am-12:22 pm

Nonstop1h 42m

$176

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/12

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sun 6/15

9:40 am-12:22 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/21

4:05 pm-4:54 pm

Nonstop1h 49m

Chicago Midway

Sun 5/25

5:50 pm-8:32 pm

Nonstop1h 42m

$206

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 6/3

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Tue 6/10

9:40 am-4:00 pm

1 stop5h 20m

$229

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 6/5

3:50 pm-6:45 pm

1 stop3h 55m

Chicago Midway

Tue 6/10

9:24 am-5:15 pm

1 stop6h 51m

$260

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/22

6:00 am-12:28 pm

1 stop7h 28m

Chicago Midway

Mon 5/26

9:16 am-4:15 pm

1 stop5h 59m

$278

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/30

12:30 pm-5:45 pm

1 stop6h 15m

Chicago Midway

Fri 6/6

9:20 am-6:31 pm

1 stop8h 11m

$301

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/6

12:35 pm-4:54 pm

1 stop5h 19m

Chicago Midway

Sun 6/22

9:40 am-4:33 pm

1 stop5h 53m

$307

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 6/5

5:55 am-4:24 pm

1 stop11h 29m

Chicago Midway

Sun 6/8

9:40 am-12:22 am

1 stop13h 42m

$322

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 5/24

7:00 am-9:13 pm

2 stops15h 13m

Chicago Midway

Mon 5/26

9:40 am-4:00 pm

1 stop5h 20m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May 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 May 1, 2025.
Read through reviews of airlines operating flights from Ontario to Chicago, 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
285 reviews

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.8

Entertainment

7.0

Comfort

8.1

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
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.8

Entertainment

7.0

Comfort

8.1

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
7,934 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.8

Entertainment

7.0

Comfort

8.1

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
285 reviews

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.8

Entertainment

7.0

Comfort

8.1

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
2,826 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.8

Entertainment

7.0

Comfort

8.1

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?

    The cheapest airlines for a one-way flight from Region of Ontario to Chicago Midway Airport are Porter Airlines ($124), APG Airlines ($125), and Air Transat ($132).

  • 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
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
Calgary to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Toronto Island to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Ottawa to Midway flights
Abbotsford to O'Hare Intl flights
Québec City to Midway flights
Calgary to Midway flights
Québec City to O'Hare Intl flights
Winnipeg to Midway flights
Edmonton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Halifax to Midway flights
Edmonton to Midway flights
London to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Regina to O'Hare Intl flights
St. John's to Midway flights
Moncton to O'Hare Intl flights
Hamilton to O'Hare Intl flights
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St John to O'Hare Intl flights
London to Midway flights
Comox to O'Hare Intl flights
Medicine Hat to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Victoria to Midway flights
Victoria to O'Hare Intl flights
Nanaimo 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$318FlexibilityNo cancel feeOn-time52%

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