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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 183

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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Toronto Island to Midway

Enter your travel dates to find the best prices.

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 6 November 2025.

Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 11/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 265
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 271
Sat 13/1211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 15/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 272
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 275
Thu 20/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 26/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/11C$ 276
Wed 19/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 22/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/11C$ 278
Sat 6/1211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 15/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 281
Tue 25/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 282
Sun 14/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 18/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/11C$ 291
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 7/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/11C$ 292
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 19/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/11C$ 295

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 6 November 2025.

Round-trip from

C$ 265

One-way from

C$ 183

Popular in

November

Cheapest in

July

Average price

C$ 595

Good round-trip deal

C$ 349 or less

Good one-way deal

C$ 199 or less
Porter Airlines
  • Porter Airlines
  • 5/12-11/12
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 10/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 25% potential increase in price (C$ 163 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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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Cheapflights Fare Finder

 
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 6 November 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago Midway Airport that are best for you.

Fly from

Toronto Island

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/11

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

Nonstop1h 50m

Chicago Midway

Mon 24/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/11

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

Nonstop1h 50m

Chicago Midway

Tue 2/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 282

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sat 6/12

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 292

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 7/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 292

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 295

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Tue 9/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/12

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

Nonstop1h 42m

C$ 310

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/11

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

Nonstop1h 50m

Chicago Midway

Tue 2/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 312

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Tue 6/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 319

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/1

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

Nonstop1h 50m

Chicago Midway

Mon 5/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 326

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 24 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Toronto Island Airport to Chicago Midway Airport

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

Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 117). Flying from Toronto Island Airport to Chicago Midway Airport in February is currently the most expensive (average of C$ 324). 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 6 November 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 54% versus a flight in the evening.

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 6 November 2025.
Check out reviews from past customers who have flown with Porter Airlines from Toronto Island Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
387 reviews
Check prices

Crew

8.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
387 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Crew

8.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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.

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

    For as low as C$ 275, Porter Airlines can have you in Chicago Midway Airport from Toronto Island Airport in 1h 50m. The distance from Toronto Island Airport to Chicago Midway Airport is about 711 km. Generally, flights for this route are direct.

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

    According to our current data, Porter Airlines (C$ 200), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 41% 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 (91%), Porter Airlines (91%) or Air Transat (91%) 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$ 325 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 171 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 188.

  • 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, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 117). Flying from Toronto Island Airport to Chicago Midway Airport in February is currently the most expensive (average of C$ 324). 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.
Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights

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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 200AverageC$ 293FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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

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