$110+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
jun. 17 — jun. 241
1 adult, Economy
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Find cheap flights from Canada to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 junio 12, 2025.
Round-trip from | $161 (iWofly) |
|---|---|
One-way from | $110 (iWofly) |
Popular in | December |
Cheapest in | April |
Average price | $253 |
Good round-trip deal | $170 or less |
Good one-way deal | $100 or less |
Find flight deals from Canada to Midway
Cheapest flights from Canada to MidwayExplore 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 junio 12, 2025.
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 junio 12, 2025.
This iWofly deal was found by Cheapflights users on 6/12. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/267:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
dom. 6/299:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12![Porter Airlines logo]()
$161
This SmartFares deal was found by Cheapflights users on 6/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/307:55 amYTZ - MDW
Nonstop1h 50mAir Transat
vie. 9/129:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 6/11![Air Transat logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/187:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
mar. 8/195:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 6/11. 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.
sáb. 10/412:15 pmYYZ - MDW
1 stop7h 21mDelta
mié. 10/159:30 amMDW - YYZ
1 stop6h 53mDelta
Deal found 6/11![Delta logo]()
$213
This FlightHub deal was found by Cheapflights users on 6/10. 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. 7/111:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
dom. 7/139:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 6/10![Porter Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 6/10. 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.
vie. 10/37:00 amYUL - MDW
1 stop10h 23mDelta
mié. 10/89:30 amMDW - YUL
1 stop5h 30mDelta
Deal found 6/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 6/11. 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. 6/176:45 amYYC - MDW
1 stop9h 55mDelta
mar. 6/241:47 pmMDW - YYC
1 stop8h 10mDelta
Deal found 6/11![Delta logo]()
$240
This FlightHub deal was found by Cheapflights users on 6/10. 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.
mié. 7/308:35 amYOW - MDW
1 stop8h 49mPorter Airlines
mar. 8/59:40 amMDW - YOW
1 stop8h 13mPorter Airlines
Deal found 6/10![Porter Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
mar. 8/58:30 pmYVR - MDW
2 stops12h 10mMultiple Airlines
mar. 8/1211:39 amMDW - YVR
1 stop11h 13mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 6/10. 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. 7/89:25 amYEG - MDW
1 stop7h 14mDelta
mar. 7/159:25 amMDW - YEG
2 stops12h 53mDelta
Deal found 6/10![Delta logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 6/11. 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. 8/1010:40 amYUL - MDW
1 stop6h 44mMultiple Airlines
lun. 8/119:40 amMDW - YUL
1 stop13h 57mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 6/11. 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. 7/246:15 amYVR - MDW
1 stop9h 24mDelta
mar. 7/291:46 pmMDW - YVR
1 stop8h 45mDelta
Deal found 6/11![Delta logo]()
$318
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 junio 12, 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
jue. 6/26
7:55 am-8:45 am
Nonstop1h 50m
Chicago Midway
dom. 6/29
9:40 am-12:22 pm
Nonstop1h 42m
$161
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
sáb. 8/30
7:55 am-8:45 am
Nonstop1h 50m
Chicago Midway
vie. 9/12
9:15 am-11:57 am
Nonstop1h 42m
$186
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
lun. 8/18
7:55 am-8:45 am
Nonstop1h 50m
Chicago Midway
mar. 8/19
5:20 pm-8:02 pm
Nonstop1h 42m
$205
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
sáb. 10/4
12:15 pm-6:36 pm
1 stop7h 21m
Chicago Midway
mié. 10/15
9:30 am-5:23 pm
1 stop6h 53m
$213
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
vie. 7/11
1:10 pm-4:24 pm
1 stop4h 14m
Chicago Midway
dom. 7/13
9:40 am-4:00 pm
1 stop5h 20m
$226
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
vie. 10/3
7:00 am-4:23 pm
1 stop10h 23m
Chicago Midway
mié. 10/8
9:30 am-4:00 pm
1 stop5h 30m
$237
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
mar. 9/9
6:40 am-5:37 pm
1 stop9h 57m
Chicago Midway
mié. 9/17
1:00 pm-8:54 pm
2 stops8h 54m
$240
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
mié. 7/30
8:35 am-4:24 pm
1 stop8h 49m
Chicago Midway
mar. 8/5
9:40 am-6:53 pm
1 stop8h 13m
$261
VancouverChicago
YVR - MDW
YVRMDW
Vancouver Intl
mar. 8/5
8:30 pm-10:40 am
2 stops12h 10m
Chicago Midway
mar. 8/12
11:39 am-8:52 pm
1 stop11h 13m
$291
EdmontonChicago
YEG - MDW
YEGMDW
Edmonton
mar. 7/8
9:25 am-5:39 pm
1 stop7h 14m
Chicago Midway
mar. 7/15
9:25 am-9:18 pm
2 stops12h 53m
$302
Showing 1-10 of 60 results
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 junio 12, 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 junio 12, 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.
Boarding
8.2
Food
7.6
Crew
8.7
Comfort
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Boarding
8.2
Food
7.6
Crew
8.7
Comfort
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Boarding
8.2
Food
7.6
Crew
8.7
Comfort
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Boarding
8.2
Food
7.6
Crew
8.7
Comfort
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Boarding
8.2
Food
7.6
Crew
8.7
Comfort
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Boarding
8.2
Food
7.6
Crew
8.7
Comfort
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
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.
Traveling to a place near Canada?
Book flights to Canada if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$169 | Average$289 | FlexibilityNo cancel fee | On-time52% |