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Cheap flights from Ontario to Chicago Midway Airport from C$ 186

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 30/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
26 Feb — 5 Mar1
1 adult

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 21 February 2025.

Round-trip from

C$ 294

One-way from

C$ 186

Popular in

December

Cheapest in

April

Average price

C$ 405

Good round-trip deal

C$ 282 or less

Good one-way deal

C$ 175 or less
Porter Airlines
  • Porter Airlines
  • 19/3-22/3
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/4
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 21 February 2025.

Thu 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/35:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/2C$ 290
Thu 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Thu 27/35:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 18/2C$ 317
Fri 18/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 19/412:55 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 20/2C$ 347
Sat 12/46:30 a.m.YYZ - MDW
1 stop13h 03mWestJet
Mon 21/41:16 p.m.MDW - YYZ
1 stop21h 18mWestJet
Deal found 20/2C$ 347
Thu 20/310:20 a.m.YYZ - MDW
1 stop3h 16mDelta
Mon 24/32:55 p.m.MDW - YYZ
1 stop6h 43mDelta
Deal found 19/2C$ 351
Sun 6/46:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Sun 13/411:15 a.m.MDW - YUL
1 stop4h 37mPorter Airlines
Deal found 20/2C$ 368
Fri 25/412:50 p.m.YUL - MDW
1 stop6h 30mDelta
Tue 29/412:48 p.m.MDW - YUL
1 stop10h 11mDelta
Deal found 20/2C$ 392
Sat 1/37:10 a.m.YYZ - MDW
1 stop13h 19mMultiple Airlines
Tue 4/38:30 a.m.MDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 18/2C$ 443
Thu 10/411:50 a.m.YUL - MDW
1 stop5h 50mMultiple Airlines
Sat 12/412:58 p.m.MDW - YUL
1 stop10h 17mMultiple Airlines
Deal found 19/2C$ 460
Thu 22/512:25 p.m.YOW - MDW
1 stop4h 59mPorter Airlines
Sat 24/59:15 a.m.MDW - YOW
1 stop7h 59mPorter Airlines
Deal found 20/2C$ 484
Sun 15/67:30 a.m.YUL - MDW
1 stop11h 33mWestJet
Sat 21/66:45 p.m.MDW - YUL
1 stop18h 13mWestJet
Deal found 19/2C$ 487
Thu 20/35:55 a.m.YOW - MDW
1 stop11h 45mMultiple Airlines
Thu 27/311:15 a.m.MDW - YOW
1 stop4h 54mMultiple Airlines
Deal found 20/2C$ 553

Find flights from Ontario to Midway within your budget

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 629,999 searches. Data last updated 21 February 2025.

Fly from

Ontario

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/3

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

Mon 24/3

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/3

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Thu 20/3

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 325

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 18/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Sat 19/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

C$ 347

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/4

6:30 a.m.-6:33 p.m.

1 stop13h 03m

Chicago Midway

Sun 20/4

10:20 a.m.-11:34 a.m.

1 stop24h 14m

C$ 347

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

Chicago Midway

Mon 24/3

2:55 p.m.-10:38 p.m.

1 stop6h 43m

C$ 351

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 6/4

6:50 a.m.-10:20 a.m.

1 stop4h 30m

Chicago Midway

Sun 13/4

11:15 a.m.-4:52 p.m.

1 stop4h 37m

C$ 368

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 25/4

12:50 p.m.-6:20 p.m.

1 stop6h 30m

Chicago Midway

Tue 29/4

12:48 p.m.-11:59 p.m.

1 stop10h 11m

C$ 392

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 1/3

7:10 a.m.-7:29 p.m.

1 stop13h 19m

Chicago Midway

Tue 4/3

8:30 a.m.-7:30 p.m.

1 stop10h 00m

C$ 443

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/4

11:50 a.m.-4:40 p.m.

1 stop5h 50m

Chicago Midway

Sat 12/4

12:58 p.m.-12:15 a.m.

1 stop10h 17m

C$ 460

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 22/5

12:25 p.m.-4:24 p.m.

1 stop4h 59m

Chicago Midway

Sat 24/5

9:15 a.m.-6:14 p.m.

1 stop7h 59m

C$ 484

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

Showing 1-10 of 31 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.

Travel insights for flights from Ontario to Midway

Get recent, data-driven insights about flights from Ontario to Midway including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 243). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 21 February 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 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 21 February 2025.
To help decide which airline to fly from Ontario to Chicago, see what other customers have to say about Delta, Porter Airlines and KLM. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

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
276 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

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

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

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
380 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

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
2,801 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

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?

    C$ 186 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on Air Transat and Delta, with prices starting from C$ 195 and C$ 219, respectively.

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

    The most popular route from Region of Ontario to Chicago Midway Airport is Toronto Pearson Intl - Chicago Midway. You may also consider Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway.

  • 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, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago Midway Airport (average of C$ 243). Flying from Region of Ontario to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 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
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
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Halifax to O'Hare Intl flights
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Calgary to Midway flights
Edmonton to Midway flights
Ottawa to Midway flights
Québec City to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Halifax to Midway flights
Hamilton to O'Hare Intl flights
Moncton to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Victoria to O'Hare Intl flights
London to O'Hare Intl flights
St John to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Kelowna to Midway flights
Regina to O'Hare Intl flights
Victoria to Midway flights
Nanaimo to O'Hare Intl flights
Grande Prairie to Midway flights
Saskatoon to Midway flights
Comox to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Kingston to O'Hare Intl flights
St. John's to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Deer Lake to O'Hare Intl flights

Top 2 airlines flying from Ontario to Midway

Discover the top 2 airlines 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 629,999 searches. Data last updated 21 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 267AverageC$ 439FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 450AverageC$ 650FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Ontario to Midway?

When you search for this flight from Ontario to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Ontario to Midway?

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Can Cheapflights find flights from Ontario to Midway with no change fees?

Certainly. Search results for flights to Midway from Ontario shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Ontario to Midway become cheaper?

Of course! You can now track prices for flights from Ontario to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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