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Cheap flights from Toronto 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.
YTO — MDW
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

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 6 November 2025.

Round-trip from

C$ 265

One-way from

C$ 183

Popular in

January

Cheapest in

September

Average price

C$ 354

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
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Porter Airlines
  • Porter Airlines
  • 10/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in November 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

Enter your travel dates to find the best prices.

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 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
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 5/11C$ 295

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 6 November 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

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

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Fri 9/1

6:30 p.m.-10:41 p.m.

1 stop3h 11m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Mon 12/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Thu 15/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 284

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Tue 13/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 284

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

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 11/12

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Sun 14/12

6:40 p.m.-11:11 p.m.

1 stop3h 31m

C$ 295

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 47 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, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 117). Flying from Toronto to Chicago Midway Airport in December is currently the most expensive (average of C$ 309). 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 6 November 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 30% versus a flight in the evening.

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 16 December 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. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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.
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
8.0
Very good
387 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

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

Boarding

8.2

Overall

8.0

Entertainment

7.0

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.
Air Transat
7.8
Good
470 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

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 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 Delta can get you from Toronto to Chicago Midway Airport in just under 1h 50m. Your travel time can differ by up to 4h 13m. 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$ 200, 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 41% 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, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 117). Flying from Toronto to Chicago Midway Airport in December is currently the most expensive (average of C$ 309). 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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 200AverageC$ 325FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 560AverageC$ 691FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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.

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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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