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$85+ Cheap flights from Midway (MDW) to Ontario

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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
gru 7 — gru 141
ndz. 12/7
ndz. 12/14
1 adult, Economy
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Find flight deals from Midway to Ontario

Cheapest flights from Midway to Ontario
Explore the most affordable flight options available from Midway to Ontario. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Listopad 7, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
czw. 11/2011:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
ndz. 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/6$188
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
pt. 12/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
ndz. 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/5$192
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
czw. 12/411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
ndz. 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/6$196
This Trip.com deal was found by Cheapflights users on 11/6. 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.
pt. 12/124:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
ndz. 12/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/6$204
This Trip.com deal was found by Cheapflights users on 11/5. 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.
czw. 12/114:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
ndz. 12/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/5$205
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
czw. 11/2011:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
wt. 11/259:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/5$211
This Trip.com deal was found by Cheapflights users on 11/5. 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.
pon. 12/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
śr. 12/109:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/5$213
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
pon. 12/111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
czw. 12/182:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/6$218
This Trip.com deal was found by Cheapflights users on 11/5. 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.
pt. 12/54:15 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
ndz. 12/79:15 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 11/5$219
This Delta deal was found by Cheapflights users on 11/5. 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.
czw. 12/119:34 amMDW - YYZ
1 stop6h 41mDelta
ndz. 12/146:05 amYYZ - MDW
1 stop3h 49mDelta
Deal found 11/5$233
This Delta deal was found by Cheapflights users on 11/5. 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.
czw. 12/49:34 amMDW - YYZ
1 stop6h 41mDelta
ndz. 12/712:13 pmYYZ - MDW
1 stop6h 47mDelta
Deal found 11/5$250
This Delta deal was found by Cheapflights users on 11/5. 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.
ndz. 12/146:40 pmMDW - YYZ
1 stop3h 31mDelta
czw. 1/16:00 amYYZ - MDW
1 stop6h 06mDelta
Deal found 11/5$261

Cheap flight deals from Midway to Ontario

Keep the following information in mind while searching for Midway to Ontario flight deals. Data was last updated Listopad 7, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$188
(Kiwi.com)

One-way from

$85
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$312

Good round-trip deal

$287 or less

Good one-way deal

$210 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Chicago Midway to Ontario
Search Deals
One-way flight from Chicago Midway to Ontario
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($34 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 November 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Ontario.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Ontario.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Ontario 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 Listopad 7, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Ontario that are best for you.

Fly from

Midway

Fly to

Ontario

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

czw. 12/4

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

ndz. 12/7

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

sob. 2/28

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

pt. 3/13

9:15 am-10:05 am

Nonstop1h 50m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

pt. 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

pt. 12/12

2:30 pm-3:20 pm

Nonstop1h 50m

$196

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

wt. 3/10

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

śr. 3/11

9:15 am-10:05 am

Nonstop1h 50m

$202

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

pt. 2/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

śr. 2/25

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

czw. 12/11

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

ndz. 12/14

9:15 am-10:05 am

Nonstop1h 50m

$205

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

pon. 3/2

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

sob. 3/14

11:00 am-11:50 am

Nonstop1h 50m

$219

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

czw. 3/5

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

sob. 3/14

11:00 am-11:50 am

Nonstop1h 50m

$221

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

śr. 4/8

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

sob. 4/11

11:00 am-11:50 am

Nonstop1h 50m

$222

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

czw. 1/15

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

pon. 1/19

9:15 am-10:05 am

Nonstop1h 50m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Ontario

Have a flexible travel schedule? Discover the best time to fly to Ontario from Midway 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 Chicago Midway Airport to Ontario

What is the cheapest month to book a flight from Chicago Midway Airport to Region of Ontario?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Region of Ontario (average of $135). Flying from Chicago Midway Airport to Region of Ontario in March is currently the most expensive (average of $473). 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 MDW to ON?

Find hourly flight availability from Midway to Ontario. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated Listopad 7, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Region of Ontario in the evening. If you’re flexible enough to do this you can expect to save up to 41% on your trip compared to booking a flight at noon.

Reviews of airlines servicing Ontario

Get insights into the airlines that provide service to Ontario. 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 Ontario. Reviews last updated Listopad 7, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Ontario, such as Porter Airlines. 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
387 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
387 reviews
Porter Airlines
8.0
Very good
387 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Related info for your journey

Find useful and relevant information for your journey from Midway to Ontario. 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 Chicago Midway Airport to Region of Ontario?

    Departing from Chicago Midway Airport to Region of Ontario will take you 1h 42m. Chicago Midway Airport and Region of Ontario are separated by a distance of 442 mi. This flight may include one or multiple stops.

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

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

  • Can I find deals for flights from Midway to Ontario that include hotel bookings?

    Yes. In addition to deals on Midway to Ontario flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Ontario?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Ontario.

  • Can I find deals for business class flights from Midway to Ontario?

    Yes. Cheapflights offers flight deals from Midway to Ontario 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 Chicago Midway Airport to Region of Ontario?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Region of Ontario (average of $135). Flying from Chicago Midway Airport to Region of Ontario in March is currently the most expensive (average of $473). 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 Midway to Ontario

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Calgary flights
Midway to Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Québec City flights
Midway to Vancouver Intl flights
Midway to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Abbotsford flights
Midway to Calgary flights
Midway to Québec City flights
O'Hare Intl to Winnipeg flights
O'Hare Intl to Ottawa flights
O'Hare Intl to Halifax flights
O'Hare Intl to Victoria flights
Midway to Halifax flights
Midway to Winnipeg flights
Midway to Ottawa flights
O'Hare Intl to Edmonton flights
Midway to Edmonton flights
O'Hare Intl to London flights
O'Hare Intl to Sydney flights
O'Hare Intl to Kelowna flights
O'Hare Intl to St. John's flights
O'Hare Intl to Fredericton flights
O'Hare Intl to Charlottetown flights
O'Hare Intl to Saskatoon flights
O'Hare Intl to Hamilton flights
O'Hare Intl to Deer Lake flights
Midway to Victoria flights
O'Hare Intl to Regina flights
Midway to Kelowna flights
Midway to St. John's flights
O'Hare Intl to Thunder Bay flights
Midway to Thunder Bay flights
Midway to Saskatoon flights
O'Hare Intl to Grande Prairie flights
O'Hare Intl to Whitehorse flights
O'Hare Intl to Penticton flights
O'Hare Intl to Campbell River flights
O'Hare Intl to Kingston flights
O'Hare Intl to Lethbridge flights

Top airline flying from Midway to Ontario

Discover the top airline that operate flights from Midway to Ontario. 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 Listopad 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$293FlexibilityNo cancel feeOn-time52%

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