$188+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Nov 21 — Nov 281
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Winnipeg with Cheapflights
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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 Midway to Winnipeg
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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 October 22, 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 October 22, 2026.
This Mytrip deal was found by Cheapflights users on 10/17. 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 12/115:02 pm -
2 stops24h 23m
Sun 12/139:35 pm -
2 stops18h 31m
Deal found 10/17![Multiple Airlines logo]()
$595
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/45:02 pm -
2 stops31h 08m
Fri 12/116:25 am -
1 stop6h 34m
Deal found 10/19![Multiple Airlines logo]()
$737
This Mytrip deal was found by Cheapflights users on 10/18. 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 11/36:42 pm -
2 stops22h 43m
Sat 11/712:35 pm -
3 stops20h 57m
Deal found 10/18![Multiple Airlines logo]()
$855
This Delta deal was found by Cheapflights users on 10/18. 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.
Fri 12/186:00 am -
1 stop8h 40m
Fri 1/87:00 am -
1 stop9h 25m
Deal found 10/18![Delta logo]()
$969
This Delta deal was found by Cheapflights users on 10/18. 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.
Wed 12/210:24 am -
1 stop7h 10m
Wed 12/96:25 am -
2 stops11h 36m
Deal found 10/18![Delta logo]()
$991
This Kissandfly.com deal was found by Cheapflights users on 10/18. 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.
Thu 11/1910:34 am -
1 stop6h 21m
Sun 11/226:35 am -
1 stop5h 15m
Deal found 10/18![KLM logo]()
$993
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Tue 12/226:52 am -
2 stops12h 58m
Wed 12/237:00 am -
1 stop18h 01m
Deal found 10/21![Multiple Airlines logo]()
$995
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 October 22, 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 October 22, 2026.
This Delta deal was found by Cheapflights users on 10/18. 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.
Fri 12/186:00 am -
1 stop8h 40m
Fri 1/87:00 am -
1 stop9h 25m
Deal found 10/18![Delta logo]()
$969
This oojo deal was found by Cheapflights users on 10/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:29 pm -
1 stop17h 25m
Sun 11/229:05 pm -
2 stops20h 34m
Deal found 10/21![WestJet logo]()
$1,093
This Booking.com deal was found by Cheapflights users on 10/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:44 pm -
3 stops18h 36m
Sun 11/227:55 pm -
2 stops14h 51m
Deal found 10/21![Multiple Airlines logo]()
$1,119
This Delta deal was found by Cheapflights users on 10/17. 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.
Fri 12/115:30 pm -
1 stop7h 09m
Sun 12/136:25 am -
1 stop5h 34m
Deal found 10/17![Delta logo]()
$1,051
This FlightHub deal was found by Cheapflights users on 10/19. 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.
Mon 12/145:30 pm -
2 stops26h 20m
Wed 12/169:35 pm -
2 stops19h 41m
Deal found 10/19![WestJet logo]()
$1,099
This Delta deal was found by Cheapflights users on 10/18. 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.
Wed 12/25:30 pm -
1 stop7h 09m
Wed 12/96:25 am -
1 stop5h 34m
Deal found 10/18![Delta logo]()
$1,051
This FlightHub deal was found by Cheapflights users on 10/18. 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.
Fri 12/189:37 am -
2 stops16h 07m
Fri 1/89:35 pm -
2 stops12h 17m
Deal found 10/18![WestJet logo]()
$1,108
This Delta deal was found by Cheapflights users on 10/17. 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.
Thu 11/1910:34 am -
1 stop6h 21m
Sun 11/226:35 am -
2 stops6h 16m
Deal found 10/17![Delta logo]()
$1,061
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 12/410:24 am -
1 stop6h 10m
Fri 12/116:25 am -
1 stop6h 34m
Deal found 10/19![Delta logo]()
$1,083
Last-minute flights from Midway to WinnipegDiscover last-minute flight deals from Midway to Winnipeg. Data last updated October 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Winnipeg. Data last updated October 22, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/18. 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 11/36:42 pm -
2 stops22h 43m
Sat 11/712:35 pm -
3 stops20h 57m
Deal found 10/18![Multiple Airlines logo]()
$855
This Kissandfly.com deal was found by Cheapflights users on 10/18. 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.
Thu 11/1910:34 am -
1 stop6h 21m
Sun 11/226:35 am -
1 stop5h 15m
Deal found 10/18![KLM logo]()
$993
This Delta deal was found by Cheapflights users on 10/17. 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.
Thu 11/1910:34 am -
1 stop6h 21m
Sun 11/2212:44 pm -
1 stop3h 55m
Deal found 10/17![Delta logo]()
$1,051
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:44 pm -
2 stops14h 31m
Sun 11/227:55 pm -
2 stops17h 56m
Deal found 10/21![Multiple Airlines logo]()
$1,030
This oojo deal was found by Cheapflights users on 10/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:44 pm -
2 stops30h 00m
Sun 11/225:45 pm -
1 stop19h 05m
Deal found 10/21![WestJet logo]()
$1,093
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:44 pm -
2 stops14h 31m
Sun 11/227:55 pm -
2 stops14h 51m
Deal found 10/21![Multiple Airlines logo]()
$1,041
This Justfly.com deal was found by Cheapflights users on 10/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:29 pm -
1 stop17h 25m
Sun 11/225:45 pm -
1 stop19h 05m
Deal found 10/21![WestJet logo]()
$1,063
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 October 22, 2026.
Search for one-way flight options from Midway to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 1/201:18 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$188
This Trip.com deal was found by Cheapflights users on 10/18. 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.
Tue 1/191:18 pm -
1 stop25h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 1/171:18 pm -
1 stop25h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 12/212:28 pm -
2 stops28h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/186:42 pm -
2 stops30h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sat 12/512:28 pm -
2 stops35h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Thu 1/211:18 pm -
3 stops43h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$260
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 October 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $433 (Kiwi.com) |
One-way from | $188 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $817 |
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 October 22, 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
Wed 12/2
12:28 pm-6:25 pm
2 stops28h 57m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 11/18
6:42 pm-2:10 am
2 stops30h 28m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 12/5
12:28 pm-7:14 pm
3 stops29h 46m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$245
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 1/21
1:18 pm-10:15 am
3 stops43h 57m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$260
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 1/20
6:01 am-11:15 am
3 stops28h 14m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$295
Quickest round-trip
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 1/20
12:30 pm-7:00 pm
1 stop5h 30m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$476
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Mon 4/19
9:30 am-7:50 pm
2 stops10h 20m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$487
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Mon 10/26
6:15 am-9:57 pm
3 stops39h 42m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$497
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 12/5
10:24 am-5:34 pm
1 stop6h 10m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$499
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 12/2
5:30 pm-1:39 am
1 stop7h 09m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$499
Showing 1-10 of 19 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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