Midway

$118+ Cheap flights from Canada to Midway (MDW)

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
abr. 27 — may. 41
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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 abril 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(Kiwi.com)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$252

Good round-trip deal

$194 or less

Good one-way deal

$184 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
From Canada to Chicago Midway
One-way flight from Canada to Chicago Midway
Highest demand for flights based on searches. 5% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in April 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 abril 22, 2025.

This go2trip.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure go2trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/63:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
vie. 6/135:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/22$191
This Trip.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/117:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
jue. 5/159:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 4/22$194
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/2212:30 pmYYZ - MDW
1 stop6h 15mDelta
lun. 5/269:16 amMDW - YYZ
1 stop6h 59mDelta
Deal found 4/22$212
This Trip.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/87:55 amYTZ - MDW
Nonstop1h 50mAir Transat
sáb. 5/109:40 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 4/21$226
This Trip.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/301:10 pmYUL - MDW
1 stop4h 44mPorter Airlines
lun. 6/29:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 4/21$230
This Kissandfly.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/912:15 pmYYZ - MDW
1 stop7h 30mKLM
dom. 5/116:25 pmMDW - YYZ
1 stop3h 33mKLM
Deal found 4/21$235
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/56:00 amYUL - MDW
1 stop3h 40mDelta
sáb. 6/75:25 pmMDW - YUL
1 stop4h 51mDelta
Deal found 4/21$238
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/36:30 amYYC - MDW
1 stop10h 15mDelta
mar. 6/101:47 pmMDW - YYC
1 stop8h 08mDelta
Deal found 4/22$250
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/86:45 amYUL - MDW
1 stop11h 09mMultiple Airlines
mié. 6/119:40 amMDW - YUL
1 stop5h 20mMultiple Airlines
Deal found 4/21$257
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/39:25 amYEG - MDW
1 stop7h 20mDelta
mar. 6/249:21 amMDW - YEG
1 stop7h 37mDelta
Deal found 4/21$258
This FlightHub deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/1810:15 amYOW - MDW
1 stop7h 09mPorter Airlines
lun. 7/219:40 amMDW - YOW
1 stop5h 53mPorter Airlines
Deal found 4/21$266
This CheapTicketsDeal deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/207:21 pmYYZ - MDW
1 stop23h 24mWestJet
mar. 5/277:25 pmMDW - YYZ
1 stop15h 15mWestJet
Deal found 4/22$269

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 2,558,603 searches. Data last updated abril 22, 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

vie. 6/6

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

vie. 6/13

5:20 pm-8:02 pm

Nonstop1h 42m

$191

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 5/11

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

jue. 5/15

9:40 am-12:22 pm

Nonstop1h 42m

$194

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 5/22

12:30 pm-5:45 pm

1 stop6h 15m

Chicago Midway

lun. 5/26

9:16 am-5:15 pm

1 stop6h 59m

$212

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 5/8

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

sáb. 5/10

9:40 am-12:22 pm

Nonstop1h 42m

$226

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 5/30

1:10 pm-4:54 pm

1 stop4h 44m

Chicago Midway

lun. 6/2

9:40 am-4:00 pm

1 stop5h 20m

$230

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 5/9

12:15 pm-6:45 pm

1 stop7h 30m

Chicago Midway

dom. 5/11

6:25 pm-10:58 pm

1 stop3h 33m

$235

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 6/5

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

vie. 6/6

4:15 pm-11:54 pm

1 stop6h 39m

$238

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mar. 6/3

6:30 am-5:45 pm

1 stop10h 15m

Chicago Midway

mar. 6/10

1:47 pm-8:55 pm

1 stop8h 08m

$250

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

dom. 6/8

6:45 am-4:54 pm

1 stop11h 09m

Chicago Midway

mié. 6/11

9:40 am-4:00 pm

1 stop5h 20m

$257

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

mar. 6/3

9:25 am-5:45 pm

1 stop7h 20m

Chicago Midway

mar. 6/24

9:21 am-3:58 pm

1 stop7h 37m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

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, April is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $160). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 abril 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 abril 22, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta and KLM from Canada to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.8

Food

7.6

Entertainment

7.0

Comfort

8.1

Overall

8.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Crew

8.8

Food

7.6

Entertainment

7.0

Comfort

8.1

Overall

8.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
8.0
Very good

Crew

8.8

Food

7.6

Entertainment

7.0

Comfort

8.1

Overall

8.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Crew

8.8

Food

7.6

Entertainment

7.0

Comfort

8.1

Overall

8.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Crew

8.8

Food

7.6

Entertainment

7.0

Comfort

8.1

Overall

8.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Crew

8.8

Food

7.6

Entertainment

7.0

Comfort

8.1

Overall

8.0

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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?

    The cheapest airlines for a one-way flight from Canada to Chicago Midway Airport are Porter Airlines ($118), Air Transat ($129), and Delta ($134).

  • 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, April is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $160). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Canada?

Book flights to Canada if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.

Top airline flying from Canada to Midway

Discover the top airline 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 2,558,603 searches. Data last updated abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$340FlexibilityNo cancel feeOn-time52%

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