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$140+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
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The best prices from Toronto to Chicago Midway are usually found in March or July, booked 24 days in advance, depart on a Wednesday or Monday and return on a Monday

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 diciembre 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$234
(Booking.com)

One-way from

$140
(Trip.com)

Popular in

February

Cheapest in

March

Average price

$268
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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High demand for flights, 1% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in December 2024
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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 diciembre 18, 2024.

This Trip.com deal was found by Cheapflights users on 12/17. 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.
lun. 12/303:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 1/131:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/17$287
This Gotogate deal was found by Cheapflights users on 12/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/289:40 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
jue. 1/25:35 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 12/18$402
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
mar. 12/317:10 amYYZ - MDW
1 stop11h 44mMultiple Airlines
mié. 1/810:57 amMDW - YYZ
1 stop5h 03mMultiple Airlines
Deal found 12/17$416
This Trip.com deal was found by Cheapflights users on 12/17. 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.
mié. 12/256:30 amYYZ - MDW
1 stop5h 38mWestJet
lun. 2/31:26 pmMDW - YYZ
1 stop8h 41mWestJet
Deal found 12/17$453
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/1912:35 pmYYZ - MDW
1 stop6h 09mDelta
dom. 2/22:08 pmMDW - YYZ
1 stop7h 44mDelta
Deal found 12/18$456

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 1/9

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

dom. 1/12

1:05 pm-3:47 pm

Nonstop1h 42m

$234

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 2/14

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

lun. 2/17

1:05 pm-3:47 pm

Nonstop1h 42m

$236

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mar. 1/7

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

lun. 2/3

6:28 pm-10:49 pm

1 stop3h 21m

$246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 1/12

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

vie. 1/17

5:30 am-4:48 pm

2 stops10h 18m

$250

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 1/9

12:20 pm-10:12 am

1 stop22h 52m

Chicago Midway

dom. 1/12

10:19 am-11:11 pm

1 stop11h 52m

$274

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 1/9

8:00 pm-11:48 am

1 stop16h 48m

Chicago Midway

dom. 1/12

12:43 pm-6:18 am

2 stops16h 35m

$322

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 5/13

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

vie. 5/16

11:15 am-1:57 pm

Nonstop1h 42m

$710

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 2/15

11:20 am-12:10 pm

Nonstop1h 50m

$140

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 1/29

7:45 am-1:08 pm

1 stop6h 23m

$140

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 1/18

7:00 am-11:29 pm

2 stops17h 29m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 13 results
1
2

Compare providers for flights from Toronto to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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 December 13, 2024.

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 October is currently the most expensive (average of $232). 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 diciembre 18, 2024.

It’s optimal to fly from Toronto to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 11% 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 diciembre 18, 2024.

The most flights from YTO to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, 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 diciembre 18, 2024.
Get a feel of what it's like to fly with Air Transat, WestJet and Porter Airlines 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
8,604 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.6

Overall

8.0

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.6

Overall

8.0

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
283 reviews
Delta
8.0
Very good
8,604 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.6

Overall

8.0

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
389 reviews
Delta
8.0
Very good
8,604 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.6

Overall

8.0

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.6

Overall

8.0

Food

7.3

Reviews

1 / 10

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 Air Transat. Our recent data shows that you can find tickets from as low as $234 on this airline. Additional options worth looking into are Porter Airlines and Delta, starting at $237 and $246 round-trip. Air Transat is 11% 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?

    $140 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 Delta and WestJet, with prices starting from $140 and $166, 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 October is currently the most expensive (average of $232). 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.

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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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$206Average$257FlexibilityNo cancel feeOn-time52%
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