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Cheap flights from Toronto to Chicago Midway Airport from C$ 188

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 19/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
15 oct. — 22 oct.1
1 adult
1 adult, Economy

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 15 septiembre 2025.

Round-trip from

C$ 323

One-way from

C$ 188

Popular in

January

Cheapest in

September

Average price

C$ 240

Good round-trip deal

C$ 242 or less

Good one-way deal

C$ 226 or less
Porter Airlines
  • Porter Airlines
  • 14/10-22/10
  • 1 total stop
  • 6h 37m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 20/10
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (C$ 46 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 September 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 15 septiembre 2025.

mar. 14/107:30 p.m.YTZ - MDW
1 stop4h 55mMultiple Airlines
mié. 22/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 15/9C$ 323
sáb. 18/106:20 a.m.YYZ - MDW
1 stop5h 10mWestJet
sáb. 25/1010:35 a.m.MDW - YYZ
1 stop5h 15mWestJet
Deal found 14/9C$ 326
sáb. 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
sáb. 25/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 332
jue. 16/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 19/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 333
mar. 14/107:30 p.m.YTZ - MDW
1 stop4h 55mMultiple Airlines
sáb. 18/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 13/9C$ 334
sáb. 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 336
mar. 28/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
mar. 4/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/9C$ 337
vie. 17/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
mar. 28/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/9C$ 338
mar. 14/107:30 p.m.YTZ - MDW
1 stop4h 55mMultiple Airlines
dom. 19/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 15/9C$ 340
lun. 6/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
jue. 9/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/9C$ 341
vie. 17/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 20/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/9C$ 343
mié. 15/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 20/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/9C$ 344

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 15 septiembre 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

mar. 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

mié. 22/10

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

Nonstop1h 42m

C$ 323

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

jue. 23/10

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

Nonstop1h 42m

C$ 323

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 13/10

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

Nonstop1h 49m

Chicago Midway

mar. 21/10

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

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 18/10

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

Nonstop1h 49m

Chicago Midway

sáb. 25/10

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

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 15/10

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

Nonstop1h 49m

Chicago Midway

lun. 20/10

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

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 17/10

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

Nonstop1h 49m

Chicago Midway

jue. 23/10

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

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 12/10

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

Nonstop1h 49m

Chicago Midway

jue. 23/10

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

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 14/10

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

Nonstop1h 49m

Chicago Midway

lun. 20/10

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

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 28/10

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

mar. 4/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 337

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 16/10

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

Nonstop1h 49m

Chicago Midway

lun. 20/10

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

Nonstop1h 42m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 42 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

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

Currently, September is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 209). 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 15 septiembre 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 22% 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 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 15 septiembre 2025.

The most flights from YTO to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 15 septiembre 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
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Crew

8.6

Comfort

7.9

Overall

7.9

Food

7.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Crew

8.6

Comfort

7.9

Overall

7.9

Food

7.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Transat
7.7
Good
438 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Crew

8.6

Comfort

7.9

Overall

7.9

Food

7.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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.

  • How long is the flight from Toronto to Chicago Midway Airport?

    Porter Airlines and WestJet can get you from Toronto to Chicago Midway Airport in just under 1h 49m. Your travel time can differ by up to 3h 21m. There are 711 km between Toronto and Chicago Midway Airport. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines flying from Toronto to Chicago Midway Airport round-trip?

    Porter Airlines, at C$ 204, 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 39% cheaper than the other options available to this destination.

  • 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, September is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 209). 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 15 septiembre 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 204AverageC$ 331FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 421AverageC$ 677FlexibilityNo 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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