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$110+ Cheap flights from Toronto (YTO) 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto to Chicago Midway are usually found in May or February, booked 34 days in advance, depart on a Monday or Wednesday and return on a Thursday

Cheap flight deals from Toronto to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$161
(iWofly)

One-way from

$110
(iWofly)

Popular in

January

Cheapest in

May

Average price

$234

Good round-trip deal

$170 or less

Good one-way deal

$100 or less
From Toronto (YTO) to Chicago Midway
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One-way flight from Toronto (YTO) to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Toronto (YTO) to Chicago Midway.
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Price to beat on a one-way flight from Toronto (YTO) to Chicago Midway.
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Find flight deals from Toronto to Midway

Cheapest flights from Toronto to Midway
Explore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This iWofly deal was found by Cheapflights users on 6/12. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/267:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 6/299:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12$161
This SmartFares deal was found by Cheapflights users on 6/11. 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.
Sat 8/307:55 amYTZ - MDW
Nonstop1h 50mAir Transat
Fri 9/129:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 6/11$186
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
Mon 8/187:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 8/195:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 6/11$205
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 10/412:15 pmYYZ - MDW
1 stop7h 21mDelta
Wed 10/159:30 amMDW - YYZ
1 stop6h 53mDelta
Deal found 6/11$213
This oojo deal was found by Cheapflights users on 6/11. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/226:30 pmYYZ - MDW
2 stops16h 15mWestJet
Tue 7/291:46 pmMDW - YYZ
2 stops15h 28mWestJet
Deal found 6/11$361

Cheapflights Fare Finder

Customize your flight search to find flights from Toronto 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 June 12, 2025.
Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.

Fly from

Toronto

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/26

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sun 6/29

9:40 am-12:22 pm

Nonstop1h 42m

$161

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 8/30

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Fri 9/12

9:15 am-11:57 am

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/18

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Tue 8/19

5:20 pm-8:02 pm

Nonstop1h 42m

$205

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/4

12:15 pm-6:36 pm

1 stop7h 21m

Chicago Midway

Wed 10/15

9:30 am-5:23 pm

1 stop6h 53m

$213

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 7/17

1:04 pm-5:39 pm

1 stop5h 35m

Chicago Midway

Thu 7/24

6:20 pm-10:58 pm

1 stop3h 38m

$353

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 7/22

6:30 pm-9:45 am

2 stops16h 15m

Chicago Midway

Tue 7/29

1:46 pm-6:14 am

2 stops15h 28m

$361

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/10

3:35 pm-4:24 pm

Nonstop1h 49m

$110

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/9

3:35 pm-4:24 pm

Nonstop1h 49m

$114

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 9/6

12:14 pm-6:37 pm

1 stop7h 23m

$135

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 6/22

6:30 am-12:29 pm

1 stop6h 59m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 13 results
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Best time to book a flight from Toronto to Midway

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

How far ahead should I book a flight from Toronto to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Midway. Price data was last updated on June 9, 2025.

The price you pay for your flight from Toronto to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 34 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Toronto to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $160). Flying from Toronto 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 YTO to MDW?

Find hourly flight availability from Toronto 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 June 12, 2025.

It’s optimal to fly from Toronto to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 14% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Toronto to Chicago Midway Airport

Explore weekly flight availability from Toronto to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from YTO to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 June 12, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and KLM from Toronto to Chicago by reading reviews from past customers. 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.
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
KLM
7.8
Good
1,358 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
396 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Comfort

8.1

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Related info for your journey

Find useful and relevant information for your journey from Toronto 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 flying from Toronto to Chicago Midway Airport round-trip?

    Our cheapest airline available from Toronto to Chicago Midway Airport is Porter Airlines. Our recent data shows that you can find tickets from as low as $161 on this airline. Additional options worth looking into are Air Transat and Delta, starting at $186 and $213 round-trip. Porter Airlines is 35% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto to Chicago Midway Airport one-way?

    $110 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 $114 and $135, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto 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 Toronto to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $160). Flying from Toronto 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 Toronto?

Book flights to Toronto if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Top airline flying from Toronto to Midway

Discover the top airline that operate flights from Toronto 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$169Average$252FlexibilityNo cancel feeOn-time52%

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