HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$103+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Toronto to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Toronto to Chicago Midway are usually found in May or February, booked 76 days in advance, depart on a Wednesday or Monday 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 July 30, 2025.

Round-trip from

$148
(SmartFares)

One-way from

$103
(SmartFares)

Popular in

January

Cheapest in

May

Average price

$274

Good round-trip deal

$170 or less

Good one-way deal

$101 or less
From Toronto (YTO) to Chicago Midway
Search Deals
One-way flight from Toronto (YTO) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Toronto (YTO) to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Toronto (YTO) to Chicago Midway.
Search Deals

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 July 30, 2025.

This SmartFares deal was found by Cheapflights users on 7/28. 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.
Fri 9/57:30 amYTZ - MDW
Nonstop1h 49mAir Transat
Sun 9/79:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 7/28$148
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Mon 8/257:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 9/49:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/27$149
This Mytrip deal was found by Cheapflights users on 7/29. 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 9/257:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 9/295:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 7/29$196
This Delta deal was found by Cheapflights users on 7/30. 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 9/1312:14 pmYYZ - MDW
1 stop7h 21mDelta
Sat 9/206:15 pmMDW - YYZ
1 stop3h 41mDelta
Deal found 7/30$212
This Justfly.com deal was found by Cheapflights users on 7/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:00 pmYYZ - MDW
2 stops26h 12mWestJet
Sat 9/67:17 pmMDW - YYZ
1 stop15h 36mWestJet
Deal found 7/27$279

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 July 30, 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

Fri 9/5

7:30 am-8:19 am

Nonstop1h 49m

Chicago Midway

Sun 9/7

9:15 am-11:57 am

Nonstop1h 42m

$148

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/25

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Thu 9/4

9:35 am-12:17 pm

Nonstop1h 42m

$149

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/25

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 9/29

5:20 pm-8:02 pm

Nonstop1h 42m

$196

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 9/13

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

Sat 9/20

6:15 pm-10:56 pm

1 stop3h 41m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 8/30

8:00 pm-9:12 pm

2 stops26h 12m

Chicago Midway

Sat 9/6

7:17 pm-11:53 am

1 stop15h 36m

$279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 8/29

9:00 am-9:50 am

Nonstop1h 50m

$103

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 9/27

7:50 am-8:39 am

Nonstop1h 49m

$106

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 9/1

6:30 am-12:28 pm

1 stop6h 58m

$135

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 8/31

11:33 am-9:12 pm

1 stop10h 39m

$152

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/6

8:45 am-6:43 pm

1 stop10h 58m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 11 results
1
2

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 July 25, 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 75 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 July 30, 2025.

It’s optimal to fly from Toronto to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 15% 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 July 30, 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).

How much does it cost to fly round-trip from Toronto to Chicago Midway Airport?

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 July 30, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta, and Air Transat from Toronto to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Boarding

8.2

Crew

8.7

Food

7.6

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Boarding

8.2

Crew

8.7

Food

7.6

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
318 reviews

Boarding

8.2

Crew

8.7

Food

7.6

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
318 reviews

Boarding

8.2

Crew

8.7

Food

7.6

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,975 reviews
Porter Airlines
8.0
Very good
318 reviews

Boarding

8.2

Crew

8.7

Food

7.6

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 $148 on this airline. Additional options worth looking into are Porter Airlines and Delta, starting at $149 and $212 round-trip. Air Transat is 41% 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?

    $103 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 $106 and $134, 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 Chicago Midway Airport?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$257FlexibilityNo cancel feeOn-time52%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.