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$131+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Toronto to Chicago Midway are usually found in July or March, booked 24 days in advance, depart on a Thursday or Saturday and return on a Saturday

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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Trip.com)

One-way from

$131
(Mytrip)

Popular in

January

Cheapest in

July

Average price

$306

Good round-trip deal

$228 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago Midway flights.
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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. 10% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/203:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 3/245:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/19$204
This Trip.com deal was found by Cheapflights users on 2/18. 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 3/203:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Thu 3/275:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 2/18$223
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/189:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 4/1912:55 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 2/20$244
This CheapTicketsDeal deal was found by Cheapflights users on 2/20. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/126:30 amYYZ - MDW
1 stop13h 03mWestJet
Sun 4/2010:20 amMDW - YYZ
1 stop24h 14mWestJet
Deal found 2/20$244
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/1812:15 pmYYZ - MDW
1 stop7h 05mDelta
Tue 4/223:02 pmMDW - YYZ
1 stop6h 53mDelta
Deal found 2/20$246
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/17:10 amYYZ - MDW
1 stop13h 19mMultiple Airlines
Tue 3/48:30 amMDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 2/20$325

Find flights from Toronto to Midway within your budget

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 February 20, 2025.

Fly from

Toronto

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 3/20

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

Mon 3/24

5:35 pm-8:17 pm

Nonstop1h 42m

$204

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 3/17

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Thu 3/20

5:35 pm-8:17 pm

Nonstop1h 42m

$229

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/18

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sat 4/19

12:55 pm-3:37 pm

Nonstop1h 42m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/12

6:30 am-6:33 pm

1 stop13h 03m

Chicago Midway

Mon 4/21

1:16 pm-11:34 am

1 stop21h 18m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

Chicago Midway

Mon 3/24

2:55 pm-10:38 pm

1 stop6h 43m

$247

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

8:00 pm-5:31 am

1 stop10h 31m

Chicago Midway

Mon 3/24

8:44 pm-9:11 pm

2 stops23h 27m

$328

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/30

9:30 am-10:20 am

Nonstop1h 50m

$131

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/28

3:35 pm-4:24 pm

Nonstop1h 49m

$132

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 5/4

7:45 am-10:40 pm

1 stop15h 55m

$136

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 13 results
1
2
  • Most accurate provider: When it comes to deals on Toronto-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Travel insights for flights from Toronto to Midway

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

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 February 14, 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 24 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 February 20, 2025.

It’s optimal to fly from Toronto to Chicago Midway Airport in the evening. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight at noon.

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 February 20, 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines 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.
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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 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 $207 on this airline. Additional options worth looking into are Air Transat and WestJet, starting at $229 and $244 round-trip. Porter Airlines is 23% 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?

    $131 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 $137 and $154, 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$209Average$261FlexibilityNo cancel feeOn-time52%
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