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$143+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Toronto to Chicago Midway are usually found in December or March, 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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

February

Cheapest in

December

Round-trip from

$228
(oojo)

One-way from

$143
(Trip.com)
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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High demand for flights, 15% potential price rise
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Best time to find cheap flights, 19% potential price drop
Search Deals
From Toronto (YTO) to Chicago Midway
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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 November 21, 2024.

This oojo deal was found by Cheapflights users on 11/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/129:40 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 12/265:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/20$228
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/129:40 amYTZ - MDW
Nonstop1h 50mAir Transat
Sun 12/1511:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/20$262
This CheapTicketsDeal deal was found by Cheapflights users on 11/20. 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.
Thu 12/126:30 amYYZ - MDW
1 stop13h 02mWestJet
Mon 12/169:38 amMDW - YYZ
1 stop12h 56mWestJet
Deal found 11/20$267
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/1210:05 amYYZ - MDW
1 stop7h 56mDelta
Mon 12/161:30 pmMDW - YYZ
1 stop8h 06mDelta
Deal found 11/20$294
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/59:40 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sun 12/85:15 amMDW - YTZ
2 stops10h 43mMultiple Airlines
Deal found 11/20$341
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/511:05 pmYYZ - MDW
2 stops15h 49mMultiple Airlines
Sun 12/85:15 amMDW - YYZ
1 stop8h 27mMultiple Airlines
Deal found 11/20$372

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Thu 12/26

5:35 pm-8:17 pm

Nonstop1h 42m

$228

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Sun 12/15

11:15 am-1:57 pm

Nonstop1h 42m

$262

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/12

6:30 am-6:32 pm

1 stop13h 02m

Chicago Midway

Mon 12/16

9:38 am-11:34 pm

1 stop12h 56m

$267

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/12

10:05 am-5:01 pm

1 stop7h 56m

Chicago Midway

Mon 12/16

1:30 pm-10:36 pm

1 stop8h 06m

$294

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/5

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Sun 12/8

5:15 am-4:58 pm

2 stops10h 43m

$341

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/5

11:05 pm-1:54 pm

2 stops15h 49m

Chicago Midway

Sun 12/8

5:15 am-2:42 pm

1 stop8h 27m

$372

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 12/14

11:10 am-12:00 pm

Nonstop1h 50m

$143

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 12/16

12:30 pm-5:01 pm

1 stop5h 31m

$165

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 1/6

3:50 pm-4:40 pm

Nonstop1h 50m

$170

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/14

12:25 pm-10:06 pm

1 stop10h 41m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November.
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 November 15, 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, December is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $159). Flying from Toronto to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 November 21, 2024.

It’s optimal to fly from Toronto to Chicago Midway Airport at noon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the morning.

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 November 21, 2024.
Get a feel of what it's like to fly with Porter Airlines, Air Transat and WestJet 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
8,758 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
8,758 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 10

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

Porter Airlines
7.8
Good
286 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
8,758 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
2,810 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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 Porter Airlines. Our recent data shows that you can find tickets from as low as $228 on this airline. Additional options worth looking into are Air Transat and WestJet, starting at $262 and $267 round-trip. Porter Airlines is 12% 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?

    $143 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 Air Transat, with prices starting from $165 and $170, 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, December is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $159). Flying from Toronto to Chicago Midway Airport in July is currently the most expensive (average of $231). 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

Browse thousands of different options on Cheapflights for your next trip

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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$205Average$254FlexibilityNo cancel feeOn-time52%
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