Cheap flights from Toronto Island (YTZ) to Midway (MDW) from $125

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 7/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
YTZ — MDW
Jun 23 — Jun 301

The best prices from Toronto Island to Chicago Midway are usually found in January or December, booked 90 days in advance, depart on a Thursday or Friday and return on a Tuesday

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 June 18, 2024.

Popular in

October

Cheapest in

January

Round-trip from

$223

One-way from

$150
High demand for flights, 27% potential price rise
Best time to find cheap flights, 23% potential price drop
From Toronto Island to Chicago Midway
One-way flight from Toronto Island to Chicago Midway

What is the cheapest day to fly round-trip from Toronto Island Airport to Chicago Midway Airport?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 35% when planning your travel around this day of the week.

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

Travelers have found it’s best to book a flight 38 days in advance to save up to 93% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Toronto Island Airport to Chicago Midway Airport 1-2 weeks in advance for as low as $315, or $488 for flights within the next 24 hours.

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

April is one of the best times of the year to fly to Chicago Midway Airport from Toronto Island Airport. Prices for April average $284 per person but you can even find prices for as low as $193. The most expensive prices can be found in the month of September. Opting for a April flight can save you 16% on your journey compared to booking in September

What is the cheapest time of day to fly from YTZ to MDW?

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 afternoon, which can drop the price by up to 20% versus a flight in the morning.

Cheap Toronto Island to Midway flights in June & July 2024

Find cheap flight options from Toronto Island to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,281,944 searches. Prices were last updated on June 18, 2024.
The lowest fares we've come across on flights traveling from Toronto to Chicago in June and July 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Fri 7/53:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/85:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$209
Mon 7/13:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 7/78:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$212
Fri 7/59:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 7/128:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$214
Mon 7/19:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/28:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$216
Tue 7/23:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/811:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$217
Fri 7/53:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/811:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$220
Wed 7/179:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 7/278:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$221
Sun 7/2110:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/235:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$222
Tue 7/23:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/108:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$223

Toronto Island to Midway 2024 flight deals

Discover exclusive flight deals for travel between Toronto Island and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,281,944 searches. Data last updated June 18, 2024.
The lowest fares we've come across on flights traveling from Toronto to Chicago in June and July 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Fri 7/53:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/85:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$209
Mon 7/13:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 7/78:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$212
Fri 7/59:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 7/128:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$214
Mon 7/19:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/28:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$216
Tue 7/23:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/811:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$217
Fri 7/53:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/811:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$220
Wed 7/179:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sat 7/278:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$221
Sun 7/2110:30 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/235:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$222
Tue 7/23:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Wed 7/108:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$223

Toronto Island to Midway flights leaving soon

Find last-minute flight options from Toronto Island to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,281,944 searches. Data last updated June 18, 2024.
Consider one of these great deals we found on last-minute flights from Toronto to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
Tue 6/253:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/25:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$285
Mon 6/248:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Mon 7/811:30 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$292
Tue 6/258:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/28:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$293
Tue 6/253:30 pmYTZ - MDW
Nonstop1h 47mAir Transat
Tue 7/25:15 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 6/18$318
Tue 6/259:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Thu 6/275:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/17$320
Tue 6/258:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Fri 6/2811:25 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$329
Wed 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 6/3012:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$333
Thu 6/273:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Tue 7/211:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$340
Wed 6/269:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Sun 6/308:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/18$345

One-way flights to Midway from Toronto Island

Search for one-way flight options from Toronto Island to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,281,944 searches. Data last updated June 18, 2024.
Take a look at some of the best available options we've come across on one-way flights from Toronto to Chicago. For those needing a return trip from Toronto, there is a search form available above.
Fri 7/53:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$125
Tue 7/238:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$127
Wed 7/33:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$128
Wed 9/113:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/18$130
Thu 9/129:20 amYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$131
Mon 7/13:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$132
Fri 9/133:30 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$133
Mon 7/18:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$134
Mon 9/168:50 pmYTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 6/17$136

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 3,281,944 searches. Data last updated June 18, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$201 - $398

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Fri 8/2

Nonstop1h 47m

Chicago Midway

Sun 8/4

Nonstop1h 42m

$201

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/19

Nonstop1h 47m

Chicago Midway

Tue 7/23

Nonstop1h 42m

$209

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Sat 8/17

Nonstop1h 47m

Chicago Midway

Sat 8/24

Nonstop1h 42m

$210

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/19

Nonstop1h 47m

Chicago Midway

Fri 8/2

Nonstop1h 42m

$212

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Tue 7/16

Nonstop1h 47m

Chicago Midway

Tue 7/23

Nonstop1h 42m

$254

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Wed 9/18

1 stop6h 43m

Chicago Midway

Sun 9/22

Nonstop1h 42m

$256

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/18

Nonstop1h 47m

Chicago Midway

Thu 7/25

Nonstop1h 42m

$262

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/24

Nonstop1h 47m

Chicago Midway

Tue 8/6

Nonstop1h 42m

$264

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/28

Nonstop1h 50m

Chicago Midway

Wed 10/30

Nonstop1h 42m

$398

Flights are sorted by cheapest first

Deals found on 6/17

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 June 14, 2024.
Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Island Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Search Deals

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

Use this chart to determine the cheapest time to fly round-trip from Toronto Island to Midway. Price data was last updated on June 16, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Toronto Island Airport to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 18, 2024.
Read reviews from past customers who have flown Air Transat and Porter Airlines 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.
7.7
Good
442 reviews

Boarding

7.8

Entertainment

7.0

Overall

7.7

Food

6.8

Crew

8.4

Comfort

7.1

Reviews

1 / 10

The flight, overall, was good. The service was fine. At the same time, while the attendants were fine, I personally would've loved to see friendlier customer service. They are smiley when we board and disembark, but in the middle they're isn't much interaction.

7.7
Good
442 reviews
7.7
Good
442 reviews

Boarding

7.8

Entertainment

7.0

Overall

7.7

Food

6.8

Crew

8.4

Comfort

7.1

Reviews

1 / 10

The flight, overall, was good. The service was fine. At the same time, while the attendants were fine, I personally would've loved to see friendlier customer service. They are smiley when we board and disembark, but in the middle they're isn't much interaction.

7.5
Good
372 reviews
7.7
Good
442 reviews

Boarding

7.8

Entertainment

7.0

Overall

7.7

Food

6.8

Crew

8.4

Comfort

7.1

Reviews

1 / 10

The flight, overall, was good. The service was fine. At the same time, while the attendants were fine, I personally would've loved to see friendlier customer service. They are smiley when we board and disembark, but in the middle they're isn't much interaction.

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.
  • Can I find flights from Toronto Island Airport to Chicago Midway Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from Toronto Island Airport to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Porter Airlines for just $201, but on average you can expect to pay $218.

  • Are there nonstop flights from Toronto Island Airport to Chicago Midway Airport for under $300 on Cheapflights?

    Cheapflights has at least 20 direct flights from Toronto Island Airport to Chicago Midway Airport under $300. A good price for a nonstop flight from Toronto Island Airport to Chicago Midway Airport is less than $218.

  • Are there last-minute flights available from Toronto Island Airport to Chicago Midway Airport for under $300?

    There are currently 20+ open flights from Toronto Island Airport to Chicago Midway Airport within the next 7 days for less than $300.

  • What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?

    Porter Airlines, at $201, was found to be the cheapest airline from Toronto Island Airport to Chicago Midway Airport.. Porter Airlines is currently priced 29% below the average price you’ll pay for this route.

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

    The top 3 most reliable airlines when flying from Toronto Island Airport to Chicago Midway Airport are Air Transat (100%), Porter Airlines (83%) and Porter Airlines (83%).

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

    The cheapest flight price from Toronto Island Airport to Chicago Midway Airport is $132. On average you can expect to pay $191. The most popular route, (Toronto Island - Chicago Midway), can usually be booked for $201.

  • What does YTZ to MDW mean?

    Toronto Island Airport is YTZ and Chicago Midway Airport is MDW. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service.

  • Can I find deals for flights from Toronto Island to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Toronto Island to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Toronto Island to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Toronto Island to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Toronto Island to Midway that allow pets onboard?

    Many airlines flying from Toronto Island to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Toronto Island to Midway?

    Yes, you can often find last-minute deals on Toronto Island to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Toronto Island Airport to Chicago Midway Airport flight deals updated?

    The Toronto Island Airport to Chicago Midway Airport flight deals you see on this page were last updated on 6/18.

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

    Currently, December is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of $140). Flying from Toronto Island Airport to Chicago Midway Airport in July is currently the most expensive (average of $240). 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.

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 3,281,944 searches. Data last updated June 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$206Average$292FlexibilityNo cancel feeOn-time52%

Search flights from Toronto Island to Midway by cabin class

Find flights from Toronto Island to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Toronto Island to Midway

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 June 18, 2024.
1%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
37%of flight departuresAfternoonNoon to 6 pm
31%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Toronto Island to Midway

Explore weekly flight availability from Toronto Island 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 June 18, 2024.
Sunday1daily flight
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday3daily flights
Friday3daily flights
Saturday1daily flight
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