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Cheap flights from Canada to Chicago Midway Airport from C$ 144

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
8 Jul — 15 Jul1
1 adult

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 3 July 2025.

Round-trip from

C$ 221

One-way from

C$ 144

Popular in

December

Cheapest in

April

Average price

C$ 343

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 154 or less
Porter Airlines
  • Porter Airlines
  • 15/7-15/7
  • Nonstop
  • 3h 32m total
  • Canada to Chicago
Porter Airlines
  • Porter Airlines
  • 12/9
  • Nonstop
  • 1h 49m total
  • Canada to Chicago
Highest demand for flights based on searches. 7% potential increase in price (C$ 40 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Canada to Chicago Midway.
Price to beat on a one-way flight from Canada to Chicago Midway.

Find flight deals from Canada to Midway

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 3 July 2025.

Fri 11/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 14/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 2/7C$ 221
Fri 5/97:30 a.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 8/99:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 1/7C$ 224
Wed 30/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Wed 6/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 1/7C$ 228
Mon 18/81:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 25/85:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 2/7C$ 292
Sat 4/1012:14 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/102:00 p.m.MDW - YYZ
1 stop7h 55mDelta
Deal found 1/7C$ 292
Fri 11/71:10 p.m.YUL - MDW
1 stop4h 14mMultiple Airlines
Mon 14/79:40 a.m.MDW - YUL
1 stop6h 40mMultiple Airlines
Deal found 2/7C$ 301
Tue 30/96:00 a.m.YUL - MDW
1 stop3h 40mDelta
Mon 6/101:05 p.m.MDW - YUL
1 stop9h 48mDelta
Deal found 2/7C$ 323
Thu 16/109:00 a.m.YWG - MDW
1 stop9h 18mMultiple Airlines
Mon 20/106:15 a.m.MDW - YWG
1 stop10h 07mMultiple Airlines
Deal found 2/7C$ 327
Mon 22/911:00 p.m.YVR - MDW
1 stop14h 58mMultiple Airlines
Tue 30/92:32 p.m.MDW - YVR
1 stop11h 06mMultiple Airlines
Deal found 1/7C$ 343
Sat 30/87:55 a.m.YYC - MDW
2 stops8h 42mDelta
Mon 1/99:30 a.m.MDW - YYC
2 stops12h 13mDelta
Deal found 2/7C$ 346
Fri 15/87:21 p.m.YYZ - MDW
1 stop18h 42mWestJet
Fri 22/812:43 p.m.MDW - YYZ
1 stop8h 15mWestJet
Deal found 2/7C$ 349
Thu 24/78:55 a.m.YYC - MDW
1 stop10h 59mMultiple Airlines
Mon 25/86:31 p.m.MDW - YYC
1 stop21h 15mMultiple Airlines
Deal found 1/7C$ 407

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 3 July 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

Tue 15/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 15/7

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

Chicago Midway

Mon 8/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 30/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 6/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 228

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:14 p.m.-6:35 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

2:00 p.m.-10:55 p.m.

1 stop7h 55m

C$ 292

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 18/8

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Mon 25/8

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 292

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 30/7

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Wed 6/8

9:40 a.m.-7:20 p.m.

1 stop8h 40m

C$ 301

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 30/9

6:00 a.m.-8:40 a.m.

1 stop3h 40m

Chicago Midway

Mon 6/10

1:05 p.m.-11:53 p.m.

1 stop9h 48m

C$ 323

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 16/10

9:00 a.m.-6:18 p.m.

1 stop9h 18m

Chicago Midway

Mon 20/10

6:15 a.m.-4:22 p.m.

1 stop10h 07m

C$ 327

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 22/9

11:00 p.m.-3:58 p.m.

1 stop14h 58m

Chicago Midway

Tue 30/9

2:32 p.m.-11:38 p.m.

1 stop11h 06m

C$ 343

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 30/8

7:55 a.m.-5:37 p.m.

2 stops8h 42m

Chicago Midway

Mon 1/9

9:30 a.m.-8:43 p.m.

2 stops12h 13m

C$ 346

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 58 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$ 238). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 3 July 2025.

When flying from Canada to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 3 July 2025.
Check out reviews from past customers who have flown with Porter Airlines,Delta, andAir Transat 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.

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
8.0
Very good

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.
  • 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$ 144 on Porter Airlines. Other airlines that offer cheap prices include Air Transat from C$ 147 and Delta from C$ 184 one-way.

  • What are the most popular routes 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$ 238). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.

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 3 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 230AverageC$ 434FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 470AverageC$ 668FlexibilityNo 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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