Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Canada to Chicago Midway Airport from C$ 180

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 20/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
16 Nov — 23 Nov1
1 adult
1 adult, Economy

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 17 October 2025.

Round-trip from

C$ 243

One-way from

C$ 180

Popular in

December

Cheapest in

July

Average price

C$ 406

Good round-trip deal

C$ 296 or less

Good one-way deal

C$ 149 or less
Porter Airlines
  • Porter Airlines
  • 8/3-11/3
  • Nonstop
  • 3h 32m total
  • Canada to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 20/11
  • Nonstop
  • 1h 50m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Canada to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Canada to Chicago Midway.
Search Deals

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 17 October 2025.

Thu 20/116:05 a.m.YYZ - MDW
1 stop3h 49mKLM
Mon 24/116:48 p.m.MDW - YYZ
1 stop3h 17mKLM
Deal found 15/10C$ 285
Thu 27/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Tue 2/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 15/10C$ 295
Thu 20/1112:08 p.m.YYZ - MDW
1 stop7h 00mDelta
Mon 24/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 15/10C$ 296
Mon 29/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/10C$ 298
Tue 11/116:35 a.m.YYC - MDW
1 stop5h 32mDelta
Tue 18/1110:47 a.m.MDW - YYC
2 stops11h 06mDelta
Deal found 15/10C$ 310
Wed 12/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 14/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/10C$ 312
Sun 9/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 13/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/10C$ 313
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/10C$ 315
Fri 5/127:30 a.m.YWG - MDW
1 stop12h 12mMultiple Airlines
Sun 7/126:15 a.m.MDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 16/10C$ 316
Sun 9/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 16/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/10C$ 317
Fri 21/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/10C$ 319
Thu 27/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sun 30/111:47 p.m.MDW - YYZ
1 stop8h 34mDelta
Deal found 15/10C$ 322

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 17 October 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 26/3

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

Nonstop1h 50m

Chicago Midway

Tue 31/3

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

Nonstop1h 42m

C$ 246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/3

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

Nonstop1h 50m

Chicago Midway

Tue 31/3

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

Nonstop1h 42m

C$ 246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 8/4

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

Nonstop1h 50m

Chicago Midway

Sat 11/4

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/4

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Tue 14/4

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

Nonstop1h 42m

C$ 272

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 26/11

12:08 p.m.-6:08 p.m.

1 stop7h 00m

Chicago Midway

Sat 29/11

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 18/3

6:00 a.m.-8:50 a.m.

1 stop3h 50m

Chicago Midway

Wed 25/3

2:00 p.m.-11:04 p.m.

1 stop8h 04m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 6/2

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

Sun 8/2

1:00 p.m.-7:09 p.m.

1 stop5h 09m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/12

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

1 stop3h 49m

Chicago Midway

Mon 8/12

1:50 p.m.-11:27 p.m.

1 stop8h 37m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/11

12:08 p.m.-6:08 p.m.

1 stop7h 00m

Chicago Midway

Mon 24/11

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 295

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 12/1

10:10 a.m.-12:35 p.m.

1 stop3h 25m

Chicago Midway

Wed 14/1

1:00 p.m.-7:09 p.m.

1 stop5h 09m

C$ 295

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/10

Showing 1-10 of 60 results
1
2
3
...
6

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$ 308). 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 17 October 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 17 October 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
381 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
381 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Transat
7.7
Good
461 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,126 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 cheapest airlines to fly from Canada to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as C$ 180 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 180 and WestJet from C$ 331 one-way.

  • 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$ 308). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Calgary to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Calgary to Midway flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Québec City to O'Hare Intl flights
Ottawa to Midway flights
Halifax to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Halifax to Midway flights
Québec City to Midway flights
Edmonton to Midway flights
Saskatoon to O'Hare Intl flights
Seattle to O'Hare Intl flights
Detroit to O'Hare Intl flights
Saskatoon to Midway flights
Hamilton to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Moncton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
London to O'Hare Intl flights
Victoria to O'Hare Intl flights
St John to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Regina to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Sudbury to O'Hare Intl flights
St. John's to O'Hare Intl flights
Victoria to Midway 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 17 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 401FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 557AverageC$ 688FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.