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Cheap flights from Canada to Chicago Midway Airport from C$ 155

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Midway

Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated 6 November 2025.

Round-trip from

C$ 265

One-way from

C$ 155

Popular in

October

Cheapest in

July

Average price

C$ 408

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
  • Canada to Chicago
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3/12
  • 3/12
  • 1 total stop
  • 17h 08m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 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 Canada to Chicago Midway.
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Price to beat on a one-way flight from Canada to Chicago Midway.
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Find flight deals from Canada to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Canada to Midway
Explore the most affordable flight options available from Canada 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 Canada 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 Canada to Chicago Midway Airport that are best for you.

Fly from

Canada

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 3/11

Showing 1-10 of 60 results
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Best time to book a flight from Canada to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Canada 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 Canada to Chicago Midway Airport

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

Currently, June is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 117). Flying from Canada 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 CA to MDW?

Find hourly flight availability from Canada 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.

It’s optimal to fly from Canada to Chicago Midway Airport at noon. By choosing this option you can save up to 6% on the cost of your flight, compared to a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Canada to Midway. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Canada 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.
Check out reviews from past customers who have flown with Porter Airlines,Air Transat, andWestJet from Canada 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

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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.
WestJet
7.2
Good
3,154 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

7.0

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 Canada 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 Canada to Chicago Midway Airport?

    Departing from Canada to Chicago Midway Airport will take you 1h 50m. The distance from Canada to Chicago Midway Airport is about 711 km. This flight may include one or multiple stops.

  • What are the most popular routes from Canada to Chicago Midway Airport?

    While some choose either Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Island - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.

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

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

  • How can I find direct flights from Canada to Midway?

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 117). Flying from Canada 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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Alternative routes for Canada to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to Midway flights
Winnipeg to O'Hare Intl flights
Calgary to Midway flights
Halifax to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Halifax to Midway flights
Edmonton to Midway flights
Québec City to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Detroit to O'Hare Intl flights
Victoria to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Kelowna to Midway flights
Regina to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Québec City to Midway flights
St. John's to O'Hare Intl flights
Seattle to O'Hare Intl flights
Victoria to Midway flights
Saskatoon to Midway flights
Sudbury to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
St John to O'Hare Intl flights
Moncton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
London to O'Hare Intl flights

Top 2 airlines flying from Canada to Midway

Discover the top 2 airlines that operate flights from Canada 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$ 400FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 560AverageC$ 691FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Canada to Midway?

Cheapflights helps you search for flights from Canada to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Canada to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Canada.

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

Yes, we can. To see specific flights from Canada to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes! Start tracking prices for Canada to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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