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$112+ Cheap flights from Midway (MDW) to Winnipeg (YWG)

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap flight deals from Midway to Winnipeg

Cheapest flights from Midway to Winnipeg
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 diciembre 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
mié. 12/102:49 pmMDW - YWG
2 stops33h 01mMultiple Airlines
dom. 12/147:30 amYWG - MDW
1 stop10h 42mMultiple Airlines
Deal found 12/9$789
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
jue. 12/253:10 pmMDW - YWG
2 stops24h 20mMultiple Airlines
dom. 12/287:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Deal found 12/10$858
This Justfly.com deal was found by Cheapflights users on 12/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/111:50 pmMDW - YWG
1 stop21h 55mWestJet
mié. 12/175:45 pmYWG - MDW
1 stop24h 33mWestJet
Deal found 12/10$1,034
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
jue. 12/117:44 amMDW - YWG
2 stops16h 58mMultiple Airlines
mié. 12/178:20 pmYWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 12/10$1,041
This FlightHub deal was found by Cheapflights users on 12/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/259:50 amMDW - YWG
1 stop29h 17mWestJet
dom. 12/288:05 pmYWG - MDW
2 stops15h 01mWestJet
Deal found 12/11$1,157
This Justfly.com deal was found by Cheapflights users on 12/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/101:50 pmMDW - YWG
1 stop9h 54mWestJet
dom. 12/145:45 pmYWG - MDW
1 stop24h 33mWestJet
Deal found 12/9$1,165

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 diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Kiwi.com)

One-way from

$112
(Trip.com)

Popular in

February

Cheapest in

May

Average price

$681
Provider with most accurate pricing for Chicago Midway-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Winnipeg flights.
Search Deals
From Chicago Midway to Winnipeg
Search Deals
One-way flight from Chicago Midway to Winnipeg
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 2,558,603 searches. Data last updated diciembre 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Winnipeg that are best for you.

Fly from

Midway

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

dom. 1/25

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

dom. 2/1

7:30 am-10:19 pm

1 stop14h 49m

$269

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 1/10

6:10 am-12:41 am

2 stops18h 31m

Winnipeg

jue. 1/15

8:20 pm-10:10 am

1 stop13h 50m

$378

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mié. 2/18

1:28 pm-11:32 am

2 stops22h 04m

Winnipeg

dom. 2/22

7:30 am-7:59 pm

1 stop12h 29m

$393

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mié. 2/18

9:50 am-7:09 pm

2 stops9h 19m

Winnipeg

dom. 2/22

5:00 am-5:37 pm

2 stops12h 37m

$547

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mié. 1/28

10:46 am-12:41 am

2 stops13h 55m

Winnipeg

mié. 2/4

6:40 am-6:36 pm

1 stop11h 56m

$569

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 1/30

9:50 am-11:03 am

1 stop25h 13m

Winnipeg

lun. 2/2

5:00 am-5:55 pm

2 stops12h 55m

$592

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 1/10

1:28 pm-12:35 am

2 stops11h 07m

Winnipeg

jue. 1/15

5:00 am-12:48 pm

2 stops7h 48m

$595

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

dom. 1/25

6:20 am-3:07 pm

1 stop8h 47m

$112

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 1/24

9:38 am-3:07 pm

1 stop29h 29m

$115

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 1/3

11:48 am-11:45 am

1 stop23h 57m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 12 results
1
2

Compare providers for flights from Midway to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Winnipeg in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Winnipeg flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Winnipeg flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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.

  • What airport do you fly into for flights to Winnipeg from Chicago Midway?

    Located just 4.6 mi from the city center, Winnipeg is the airport most travelers will use when flying to Winnipeg from Chicago Midway. Booking flights from Chicago Midway to Winnipeg (YWG) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 0 different airlines.

  • Can I find deals for flights from Midway to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Midway to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Winnipeg.

  • Can I find deals for business class flights from Midway to Winnipeg?

    Yes. Cheapflights offers flight deals from Midway to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Winnipeg?

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Portage la Prairie

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