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Cheap flights from Toronto to Chicago Midway Airport from C$ 186

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 30/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
26 feb. — 5 mar.1
1 adult

The best prices from Toronto to Chicago Midway are usually found in July or March, booked 24 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 21 febrero 2025.

Round-trip from

C$ 294

One-way from

C$ 186

Popular in

January

Cheapest in

July

Average price

C$ 435

Good round-trip deal

C$ 282 or less

Good one-way deal

C$ 175 or less
Porter Airlines
  • Porter Airlines
  • 19/3-22/3
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 10% potential increase in price (C$ 62 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 February 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 21 febrero 2025.

jue. 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 24/35:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/2C$ 290
jue. 20/33:50 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
jue. 27/35:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 18/2C$ 317
vie. 18/49:30 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
sáb. 19/412:55 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 20/2C$ 347
sáb. 12/46:30 a.m.YYZ - MDW
1 stop13h 03mWestJet
lun. 21/41:16 p.m.MDW - YYZ
1 stop21h 18mWestJet
Deal found 20/2C$ 347
jue. 20/310:20 a.m.YYZ - MDW
1 stop3h 16mDelta
lun. 24/32:55 p.m.MDW - YYZ
1 stop6h 43mDelta
Deal found 19/2C$ 351
sáb. 1/37:10 a.m.YYZ - MDW
1 stop13h 19mMultiple Airlines
mar. 4/38:30 a.m.MDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 18/2C$ 443

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 629,999 searches. Data last updated 21 febrero 2025.

Fly from

Toronto

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 20/3

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

lun. 24/3

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

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 17/3

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

Nonstop1h 50m

Chicago Midway

jue. 20/3

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

Nonstop1h 42m

C$ 325

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 18/4

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

Nonstop1h 50m

Chicago Midway

sáb. 19/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

C$ 347

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 12/4

6:30 a.m.-6:33 p.m.

1 stop13h 03m

Chicago Midway

dom. 20/4

10:20 a.m.-11:34 a.m.

1 stop24h 14m

C$ 347

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

Chicago Midway

lun. 24/3

2:55 p.m.-10:38 p.m.

1 stop6h 43m

C$ 351

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 1/3

7:10 a.m.-7:29 p.m.

1 stop13h 19m

Chicago Midway

mar. 4/3

8:30 a.m.-7:30 p.m.

1 stop10h 00m

C$ 443

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 30/4

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

Nonstop1h 50m

C$ 186

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

dom. 4/5

7:45 a.m.-10:40 p.m.

1 stop15h 55m

C$ 193

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 20/3

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

Nonstop1h 50m

C$ 197

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

C$ 219

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

Showing 1-10 of 13 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.

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 14 February 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 24 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 21 febrero 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 Monday 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 21 febrero 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
8,220 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
276 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
1,333 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
380 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
2,801 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

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$ 294, was found to be the cheapest airline from Toronto to Chicago Midway Airport.Alternate airlines to your destination round-trip include Air Transat and WestJet. Users have found that Porter Airlines is 23% 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$ 186), Air Transat (C$ 195), and Delta (C$ 219).

  • 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

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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 21 febrero 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 267AverageC$ 377FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 450AverageC$ 650FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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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