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Midway

$122+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
nov. 9 — nov. 161
dom. 11/9
dom. 11/16
1 adult, Economy
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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 octubre 10, 2025.

This Delta deal was found by Cheapflights users on 10/8. 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.
mié. 10/296:15 amYYZ - MDW
1 stop7h 13mDelta
vie. 10/319:35 amMDW - YYZ
1 stop6h 44mDelta
Deal found 10/8$202
This SmartFares deal was found by Cheapflights users on 10/9. 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.
jue. 11/209:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 11/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/9$208
This Delta deal was found by Cheapflights users on 10/8. 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.
jue. 11/206:05 amYYZ - MDW
1 stop3h 49mDelta
lun. 11/246:48 pmMDW - YYZ
1 stop3h 17mDelta
Deal found 10/8$211
This Trip.com deal was found by Cheapflights users on 10/9. 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.
vie. 11/219:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 11/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/9$212
This SmartFares deal was found by Cheapflights users on 10/8. 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.
jue. 11/202:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
dom. 11/2311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/8$213
This Jettzy deal was found by Cheapflights users on 10/8. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/39:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
jue. 11/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/8$214
This FlightHub deal was found by Cheapflights users on 10/7. 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.
mar. 11/49:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
mar. 11/1111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/7$215
This FlightHub deal was found by Cheapflights users on 10/8. 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.
mar. 11/49:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
jue. 11/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/8$216
This SmartFares deal was found by Cheapflights users on 10/9. 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.
jue. 11/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
jue. 11/134:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/9$218
This Mytrip deal was found by Cheapflights users on 10/8. 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.
jue. 11/62:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
dom. 11/911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/8$220
This SmartFares deal was found by Cheapflights users on 10/7. 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.
mié. 11/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 11/104:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/7$224
This Mytrip deal was found by Cheapflights users on 10/9. 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.
vie. 11/219:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
dom. 11/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/9$225

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 octubre 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$178
(FlightHub)

One-way from

$122
(SmartFares)

Popular in

December

Cheapest in

July

Average price

$284

Good round-trip deal

$252 or less

Good one-way deal

$143 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
Search Deals
From Ontario to Chicago Midway
Search Deals
One-way flight from Ontario to Chicago Midway
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Ontario to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Ontario to Chicago Midway.
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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 octubre 10, 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

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 10/29

6:15 am-12:28 pm

1 stop7h 13m

Chicago Midway

vie. 10/31

9:35 am-5:19 pm

1 stop6h 44m

$202

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 10/29

6:15 am-12:28 pm

1 stop7h 13m

Chicago Midway

sáb. 11/1

3:00 pm-11:18 pm

1 stop7h 18m

$202

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 11/20

12:08 pm-6:08 pm

1 stop7h 00m

Chicago Midway

lun. 11/24

6:48 pm-11:05 pm

1 stop3h 17m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 2/6

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

dom. 2/8

1:00 pm-7:09 pm

1 stop5h 09m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 11/5

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

mié. 11/12

9:34 am-2:48 pm

1 stop4h 14m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mar. 3/24

6:00 am-12:35 pm

1 stop7h 35m

Chicago Midway

mié. 3/25

2:00 pm-11:04 pm

1 stop8h 04m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 11/21

12:08 pm-6:14 pm

1 stop7h 06m

Chicago Midway

lun. 11/24

6:48 pm-11:05 pm

1 stop3h 17m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 11/22

10:05 am-12:46 pm

1 stop3h 41m

Chicago Midway

sáb. 11/29

6:48 pm-11:05 pm

1 stop3h 17m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

lun. 1/12

7:45 am-12:35 pm

1 stop5h 50m

Chicago Midway

sáb. 1/31

1:00 pm-7:09 pm

1 stop5h 09m

$211

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 11/21

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

lun. 11/24

11:00 am-1:42 pm

Nonstop1h 42m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 60 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 $83). Flying from Region of Ontario to Chicago Midway Airport in December is currently the most expensive (average of $219). 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 octubre 10, 2025.

It’s typically best to fly out from Region of Ontario to Chicago Midway Airport at noon. Doing so could potentially save you 35% on the flight price compared to flying in the evening, which is usually more expensive.

How much does it cost to fly round-trip from Region of Ontario to Chicago Midway Airport?

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.

  • How long is the flight from Region of Ontario to Chicago Midway Airport?

    A quick flight from Region of Ontario to Chicago Midway Airport can take about 1h 50m. Delta provides one of the quickest options available for as low as $212. There are 442 mi between Region of Ontario and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 ($130), Delta ($134), and Air Transat ($136).

  • 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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of $83). Flying from Region of Ontario to Chicago Midway Airport in December is currently the most expensive (average of $219). 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
Porter
Benton Harbor
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Abbotsford to O'Hare Intl flights
Québec City to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Halifax to Midway flights
Ottawa to Midway flights
Calgary to Midway flights
Winnipeg to Midway flights
Québec City to Midway flights
Edmonton to Midway flights
Kelowna to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Victoria to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
London to O'Hare Intl flights
Victoria to Midway flights
Moncton to O'Hare Intl flights
Regina to O'Hare Intl flights
London to Midway flights
St John to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
St. John's to Midway flights
Medicine Hat to O'Hare Intl flights
Comox 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 octubre 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$265FlexibilityNo cancel feeOn-time52%

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