$160+ Cheap flights from Midway (MDW) to Winnipeg (YWG)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Winnipeg 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Midway to Winnipeg
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to WinnipegExplore the most affordable flight options available from Midway to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Midway to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Fri 10/26:05 pm -
1 stop16h 55m
Deal found 9/10![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Sat 10/34:15 pm -
2 stops18h 45m
Deal found 9/10![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:20 pm -
2 stops19h 23m
Fri 10/27:55 pm -
1 stop15h 05m
Deal found 9/10![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/23:20 pm -
1 stop9h 35m
Sun 10/49:05 pm -
2 stops17h 30m
Deal found 9/8![Multiple Airlines logo]()
$383
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
2 stops20h 55m
Fri 10/22:55 pm -
2 stops20h 05m
Deal found 9/10![Multiple Airlines logo]()
$438
Best flights from Midway to WinnipegDiscover carefully curated flight deals from Midway to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Midway to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Fri 10/26:05 pm -
1 stop16h 55m
Deal found 9/10![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
1 stop9h 35m
Fri 10/29:05 pm -
2 stops17h 30m
Deal found 9/10![Multiple Airlines logo]()
$375
This Porter Airlines deal was found by Cheapflights users on 9/5. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:20 pm -
2 stops26h 38m
Tue 9/2911:15 am -
2 stops23h 45m
Deal found 9/5![Porter Airlines logo]()
$772
This Justfly.com deal was found by Cheapflights users on 9/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/89:55 am -
2 stops9h 55m
Sun 1/178:05 pm -
2 stops36h 40m
Deal found 9/5![WestJet logo]()
$806
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:20 pm -
2 stops20h 55m
Fri 10/29:05 pm -
2 stops17h 30m
Deal found 9/10![Multiple Airlines logo]()
$420
This Mytrip deal was found by Cheapflights users on 9/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:20 pm -
3 stops24h 05m
Sun 10/42:55 pm -
3 stops20h 05m
Deal found 9/8![Multiple Airlines logo]()
$609
This Porter Airlines deal was found by Cheapflights users on 9/6. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:20 pm -
2 stops26h 38m
Mon 10/1911:40 am -
2 stops23h 20m
Deal found 9/6![Porter Airlines logo]()
$792
Last-minute flights from Midway to WinnipegDiscover last-minute flight deals from Midway to Winnipeg. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Winnipeg. Data last updated September 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:20 pm -
2 stops19h 23m
Fri 10/27:55 pm -
1 stop15h 05m
Deal found 9/10![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Fri 10/26:05 pm -
1 stop16h 55m
Deal found 9/10![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Sat 10/34:15 pm -
2 stops18h 45m
Deal found 9/10![Multiple Airlines logo]()
$348
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
2 stops20h 55m
Fri 10/22:55 pm -
2 stops20h 05m
Deal found 9/10![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/23:20 pm -
1 stop9h 35m
Sun 10/49:05 pm -
2 stops17h 30m
Deal found 9/8![Multiple Airlines logo]()
$383
One-way flights from Midway to WinnipegSearch for one-way flight options from Midway to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Midway to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Mon 10/1911:45 am -
1 stop13h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/43:20 pm -
2 stops26h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Porter Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Tue 11/176:16 am -
2 stops17h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 11/126:42 pm -
2 stops21h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 11/136:16 am -
2 stops17h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 9/2711:45 am -
2 stops30h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 10/256:40 pm -
2 stops22h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Thu 10/296:42 pm -
2 stops22h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/36:25 am -
2 stops33h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/233:20 pm -
2 stops26h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Porter Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 11/166:16 am -
3 stops28h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$230
Find flight deals from Midway to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $346 (Kiwi.com) |
One-way from | $160 (Trip.com) |
Popular in | August |
Cheapest in | February |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Winnipeg 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 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 10/23
6:15 am-12:55 am
3 stops18h 40m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$206
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sun 10/4
3:20 pm-2:05 pm
3 stops22h 45m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$263
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 9/19
1:06 pm-12:15 pm
3 stops47h 09m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$315
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 11/14
6:00 am-11:29 pm
2 stops17h 29m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$316
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 9/18
12:54 pm-5:25 pm
3 stops28h 31m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$320
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 9/30
3:20 pm-9:45 am
1 stop18h 25m
Winnipeg
Fri 10/2
6:05 pm-11:00 am
1 stop16h 55m
$346
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 10/1
3:20 pm-12:55 am
1 stop9h 35m
Winnipeg
Fri 10/2
9:05 pm-2:35 pm
2 stops17h 30m
$375
Quickest round-trip
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 11/17
12:30 pm-4:42 pm
1 stop4h 12m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$389
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 11/18
10:34 am-4:42 pm
1 stop6h 08m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$389
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 10/27
9:29 am-12:44 am
2 stops15h 15m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$405
Showing 1-10 of 16 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Midway with our price prediction graph.
MDW-YWG
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.
Related info for your journey
Find useful and relevant information for your journey from Midway to Winnipeg. 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 Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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