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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 210

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 28/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
27 Jan — 3 Feb1
1 adult

The best prices from Toronto Island to Chicago Midway are usually found in May or July, booked 90 days in advance, depart on a Wednesday or Monday and return on a Saturday

Cheap flight deals from Toronto Island to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) 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 22 January 2025.

Round-trip from

C$ 340

One-way from

C$ 210

Popular in

November

Cheapest in

May

Average price

C$ 371

Good round-trip deal

C$ 336 or less

Good one-way deal

C$ 219 or less
Porter Airlines
  • Porter Airlines
  • 13/2-17/2
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Air Transat
  • Air Transat
  • 28/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Price to beat on a round-trip flight from Toronto Island to Chicago Midway.
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Price to beat on a one-way flight from Toronto Island to Chicago Midway.
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Find flight deals from Toronto Island to Midway

Cheapest flights from Toronto Island to Midway
Explore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 January 2025.

Thu 13/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 17/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/1C$ 340
Thu 13/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Wed 19/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 21/1C$ 347
Wed 26/211:20 a.m.YTZ - MDW
1 stop8h 03mMultiple Airlines
Sun 2/311:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 21/1C$ 354

Find flights from Toronto Island to Midway within your budget

Customize your flight search to find flights from Toronto Island 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 22 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Mon 17/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 340

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Wed 19/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 347

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 26/2

11:20 a.m.-6:23 p.m.

1 stop8h 03m

Chicago Midway

Sun 2/3

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

Nonstop1h 42m

C$ 354

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 16/6

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

Nonstop1h 50m

C$ 227

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/3

11:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/1

Best time to book a flight from Toronto Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto Island 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 Island to Midway

Get recent, data-driven insights about flights from Toronto Island to Midway including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Toronto Island Airport to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Toronto Island to Midway. Price data was last updated on 17 January 2025.

To ensure you get the cheapest price possible for a flight from Toronto Island Airport to Chicago Midway Airport, you should look to book at least 89 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 Island Airport to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 243). Flying from Toronto Island Airport 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 YTZ to MDW?

Find hourly flight availability from Toronto Island 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 22 January 2025.

When flying from Toronto Island Airport 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 3% versus a flight in the afternoon.

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 22 January 2025.
Porter Airlines
7.9
Good
277 reviews
Check prices

Entertainment

6.9

Food

7.6

Comfort

8.0

Crew

8.7

Boarding

8.2

Overall

7.9

Reviews

1 / 10

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Porter Airlines
7.9
Good
277 reviews
Porter Airlines
7.9
Good
277 reviews
Check prices

Entertainment

6.9

Food

7.6

Comfort

8.0

Crew

8.7

Boarding

8.2

Overall

7.9

Reviews

1 / 10

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Air Transat
7.8
Good
381 reviews
Porter Airlines
7.9
Good
277 reviews
Check prices

Entertainment

6.9

Food

7.6

Comfort

8.0

Crew

8.7

Boarding

8.2

Overall

7.9

Reviews

1 / 10

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Related info for your journey

Find useful and relevant information for your journey from Toronto Island 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 Island Airport to Chicago Midway Airport round-trip?

    According to our current data, Porter Airlines (C$ 340), and Air Transat (C$ 347) offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 12% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Toronto Island Airport to Chicago Midway Airport?

    No one likes to see their flight delayed. When booking a flight from Toronto Island Airport to Chicago Midway Airport consider choosing Porter Airlines (68%), Porter Airlines (68%) or Air Transat (68%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Toronto Island Airport to Chicago Midway Airport?

    On average you can expect to pay C$ 326 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 175 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 259.

  • Can I find deals for flights from Toronto Island to Midway that include hotel bookings?

    Yes. In addition to deals on Toronto Island to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto Island to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto Island to Midway.

  • Can I find deals for business class flights from Toronto Island to Midway?

    Yes. Cheapflights offers flight deals from Toronto Island 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 Island Airport to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 243). Flying from Toronto Island Airport 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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Alternative routes for Toronto Island to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Toronto Island to Midway

Discover the top airline that operate flights from Toronto Island 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 22 January 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 291AverageC$ 387FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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

Cheapflights makes it easy to find Toronto Island to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

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

Yes! Cheapflights helps users easily find flights from Toronto Island to Midway with no change fees.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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