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Cheap flights from Toronto to Chicago Midway Airport from C$ 177

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 20/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
2 Apr — 9 Apr1
1 adult

Cheapflights Tip: The best prices from Toronto to Chicago Midway are usually found in February or July, booked 42 days in advance, depart on a Wednesday or Tuesday 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 28 March 2025.

Round-trip from

C$ 280

One-way from

C$ 177

Popular in

January

Cheapest in

February

Average price

C$ 366

Good round-trip deal

C$ 277 or less

Good one-way deal

C$ 215 or less
Porter Airlines
  • Porter Airlines
  • 19/4-26/4
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 20/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (C$ 14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 12 potential savings vs. average RT price).
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Average for round-trip flights in March 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 28 March 2025.

Sat 19/411:10 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 20/45:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/3C$ 282
Tue 29/49:30 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 3/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 27/3C$ 319
Wed 23/412:54 p.m.YYZ - MDW
1 stop5h 25mDelta
Wed 30/45:59 p.m.MDW - YYZ
1 stop3h 56mDelta
Deal found 26/3C$ 320
Thu 10/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 17/411:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 27/3C$ 399
Wed 30/46:30 a.m.YYZ - MDW
1 stop11h 49mWestJet
Fri 2/510:20 a.m.MDW - YYZ
1 stop11h 55mWestJet
Deal found 27/3C$ 416
Thu 10/47:25 p.m.YYZ - MDW
1 stop10h 58mMultiple Airlines
Wed 16/43:00 p.m.MDW - YYZ
1 stop7h 54mMultiple Airlines
Deal found 27/3C$ 476

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 28 March 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

Sat 19/4

11:10 a.m.-12:00 p.m.

Nonstop1h 50m

Chicago Midway

Sun 20/4

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 282

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 29/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Sat 3/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 319

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 23/4

12:54 p.m.-5:19 p.m.

1 stop5h 25m

Chicago Midway

Wed 30/4

5:59 p.m.-10:55 p.m.

1 stop3h 56m

C$ 320

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Thu 17/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 399

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 30/4

6:30 a.m.-5:19 p.m.

1 stop11h 49m

Chicago Midway

Fri 2/5

10:20 a.m.-11:15 p.m.

1 stop11h 55m

C$ 416

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/4

7:25 p.m.-5:23 a.m.

1 stop10h 58m

Chicago Midway

Wed 16/4

3:00 p.m.-11:54 p.m.

1 stop7h 54m

C$ 476

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 20/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

C$ 177

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 12/5

4:05 p.m.-4:54 p.m.

Nonstop1h 49m

C$ 193

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 23/4

3:59 p.m.-6:20 p.m.

1 stop3h 21m

C$ 199

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 21/5

4:00 p.m.-8:17 p.m.

1 stop29h 17m

C$ 247

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/3

Showing 1-10 of 12 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 21 March 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 42 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, January is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 243). 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 28 March 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 39% versus a flight at noon.

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 30 June 2024.

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

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 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 28 March 2025.
Read reviews from past customers who have flown Delta, Porter Airlines and KLM from Toronto to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
7,897 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
277 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
1,321 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
381 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
2,788 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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?

    Porter Airlines, at C$ 280, was found to be the cheapest airline from Toronto to Chicago Midway Airport.Alternate airlines to your destination round-trip include Air Transat and Delta. Users have found that Porter Airlines is 25% 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$ 177), Delta (C$ 193), and Air Transat (C$ 199).

  • 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, January is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 243). 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 28 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 269AverageC$ 390FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 493AverageC$ 700FlexibilityNo 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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