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Cheap flights from Toronto to Chicago Midway Airport from C$ 146

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
19 Aug — 26 Aug1
1 adult

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 Tuesday or Wednesday and return on a Tuesday

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 14 August 2025.

Round-trip from

C$ 240

One-way from

C$ 146

Popular in

January

Cheapest in

May

Average price

C$ 361

Good round-trip deal

C$ 216 or less

Good one-way deal

C$ 128 or less
Porter Airlines
  • Porter Airlines
  • 5/9-7/9
  • Nonstop
  • 3h 31m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 8/9
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 38 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in August 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 14 August 2025.

Fri 5/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 8/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 240
Fri 26/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/8C$ 241
Thu 2/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 243
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 23/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 247
Fri 19/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 21/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 248
Sat 6/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 7/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 250
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 15/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 251
Sun 7/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 252
Fri 26/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 26/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 254
Thu 30/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 4/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 255
Sun 23/116:00 a.m.YYZ - MDW
1 stop7h 32mDelta
Wed 26/111:00 p.m.MDW - YYZ
1 stop3h 23mDelta
Deal found 13/8C$ 292
Sat 27/96:30 a.m.YYZ - MDW
1 stop6h 58mDelta
Sat 4/109:35 a.m.MDW - YYZ
1 stop6h 44mDelta
Deal found 13/8C$ 309

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 629,999 searches. Data last updated 14 August 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 2/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 5/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 8/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 7/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 27/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Fri 3/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 30/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 10/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Wed 17/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 24/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 26/10

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 13/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 20/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Fri 19/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

Showing 1-10 of 43 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 8 August 2025.

To ensure you get the cheapest price possible for a flight from Toronto to Chicago Midway Airport, you should look to book at least 75 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 233). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 14 August 2025.

When flying from Toronto to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 31% versus a flight in the afternoon.

What is the cheapest day to fly from Toronto to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Midway. Price data was last updated on 20 October 2024.

Travelers seeking maximum savings on their Toronto to Chicago Midway Airport flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 14 August 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 14 August 2025.
Get a feel of what it's like to fly with Porter Airlines and Air Transat from Toronto to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Crew

8.7

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
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Crew

8.7

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
427 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Crew

8.7

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?

    Porter Airlines, at C$ 202, was found to be the cheapest airline from Toronto to Chicago Midway Airport. An alternate airline flying to your destination would be WestJet. Users have found that Porter Airlines is 41% cheaper than the other options available to this destination.

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

    The cheapest airlines for a one-way flight from Toronto to Chicago Midway Airport are Porter Airlines (C$ 146), Delta (C$ 185), and WestJet (C$ 194).

  • 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, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 233). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 2 airlines flying from Toronto to Midway

Discover the top 2 airlines 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 629,999 searches. Data last updated 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 202AverageC$ 339FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 475AverageC$ 600FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Toronto to Midway?

When you search for this flight from Toronto to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Toronto to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Toronto to Midway.

Can Cheapflights find flights from Toronto to Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Toronto to Midway flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Toronto to Midway become cheaper?

Yes, Cheapflights offers price alerts on Toronto to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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