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$139+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
feb. 26 — mar. 51
jue. 2/26
jue. 3/5
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 enero 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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. 3/37:30 am
MDW
-
YWG
2 stops17h 10m
Multiple Airlines
mié. 3/47:30 am
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Deal found 1/26$369
This FlightHub deal was found by Cheapflights users on 1/26. 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.
mar. 3/31:29 pm
MDW
-
YWG
2 stops11h 10m
WestJet
mié. 3/45:00 am
YWG
-
MDW
2 stops7h 46m
WestJet
Deal found 1/26$496
This FlightHub deal was found by Cheapflights users on 1/26. 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.
lun. 4/137:16 pm
MDW
-
YWG
1 stop15h 40m
WestJet
dom. 4/1911:55 am
YWG
-
MDW
1 stop6h 41m
WestJet
Deal found 1/26$520
This FlightHub deal was found by Cheapflights users on 1/25. 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.
lun. 2/99:53 am
MDW
-
YWG
1 stop25h 10m
WestJet
mié. 2/117:30 am
YWG
-
MDW
1 stop9h 59m
WestJet
Deal found 1/25$523
This WestJet deal was found by Cheapflights users on 1/25. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/129:30 am
MDW
-
YWG
1 stop25h 31m
WestJet
lun. 3/1612:20 pm
YWG
-
MDW
2 stops21h 36m
WestJet
Deal found 1/25$605
This WestJet deal was found by Cheapflights users on 1/25. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/129:30 am
MDW
-
YWG
2 stops9h 39m
WestJet
jue. 3/1912:55 pm
YWG
-
MDW
2 stops29h 45m
WestJet
Deal found 1/25$618
This WestJet deal was found by Cheapflights users on 1/24. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/199:50 am
MDW
-
YWG
2 stops9h 19m
WestJet
lun. 2/235:00 am
YWG
-
MDW
2 stops12h 37m
WestJet
Deal found 1/24$619
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/89:20 am
MDW
-
YWG
2 stops12h 05m
WestJet
mar. 9/157:00 am
YWG
-
MDW
2 stops14h 46m
WestJet
Deal found 1/27$622

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 enero 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$1,231
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. 30% potential increase in price ($274 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 enero 27, 2026.
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

mar. 3/3

7:30 am-12:40 am

2 stops17h 10m

Winnipeg

mié. 3/4

7:30 am-7:07 pm

1 stop11h 37m

$369

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 3/3

9:50 am-7:09 pm

2 stops9h 19m

Winnipeg

mié. 3/4

5:00 am-12:46 pm

2 stops7h 46m

$502

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

lun. 4/13

7:16 pm-10:56 am

1 stop15h 40m

Winnipeg

dom. 4/19

11:55 am-6:36 pm

1 stop6h 41m

$520

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

lun. 2/9

9:53 am-11:03 am

1 stop25h 10m

Winnipeg

mié. 2/11

7:30 am-5:29 pm

1 stop9h 59m

$523

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 3/12

9:30 am-11:01 am

1 stop25h 31m

Winnipeg

lun. 3/16

12:20 pm-9:56 am

2 stops21h 36m

$605

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 3/12

9:30 am-11:01 am

1 stop25h 31m

Winnipeg

jue. 3/19

12:20 pm-8:53 am

2 stops20h 33m

$605

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 2/19

7:20 pm-7:09 pm

2 stops23h 49m

Winnipeg

lun. 2/23

5:00 am-12:46 pm

2 stops31h 46m

$619

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 4/24

4:15 pm-8:40 am

1 stop16h 25m

$139

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 2/28

12:50 pm-12:35 am

1 stop11h 45m

$147

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 2/27

11:05 am-11:32 am

1 stop24h 27m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 14 results
1
2
  • 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.
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.

  • How long is the flight from Chicago Midway Airport to Winnipeg?

    Airlines like WestJet fly from Chicago Midway Airport to Winnipeg in about 9h 19m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago Midway Airport and Winnipeg is about 722 mi.

  • 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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