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$207+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:20 pm
MDW
-
YWG
1 stop23h 59m
Multiple Airlines
Sat 5/236:05 am
YWG
-
MDW
2 stops15h 57m
Multiple Airlines
Deal found 4/24$374
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:20 pm
MDW
-
YWG
1 stop17h 20m
Multiple Airlines
Sun 5/3111:40 am
YWG
-
MDW
2 stops22h 00m
Multiple Airlines
Deal found 4/25$457
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:15 am
MDW
-
YWG
1 stop9h 34m
Multiple Airlines
Thu 6/45:10 pm
YWG
-
MDW
1 stop16h 30m
Multiple Airlines
Deal found 4/27$484
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
MDW
-
YWG
1 stop9h 19m
Porter Airlines
Sun 5/3111:40 am
YWG
-
MDW
2 stops22h 00m
Porter Airlines
Deal found 4/25$500
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/2310:30 am
MDW
-
YWG
1 stop22h 10m
Multiple Airlines
Sat 5/309:25 am
YWG
-
MDW
1 stop24h 20m
Multiple Airlines
Deal found 4/23$505
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/73:20 pm
MDW
-
YWG
1 stop17h 20m
Multiple Airlines
Sat 5/309:25 am
YWG
-
MDW
1 stop24h 20m
Multiple Airlines
Deal found 4/23$549
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 7/13:20 pm
MDW
-
YWG
1 stop23h 59m
Multiple Airlines
Fri 7/318:10 pm
YWG
-
MDW
1 stop13h 30m
Multiple Airlines
Deal found 4/23$570

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$374
(Kiwi.com)

One-way from

$207
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$535
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. 22% potential increase in price ($178 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 28, 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

Price

Cheapest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/2

6:36 pm-5:58 pm

3 stops23h 22m

Winnipeg

Thu 6/4

4:15 pm-9:35 am

2 stops17h 20m

$583

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/5

9:22 am-12:55 am

2 stops15h 33m

Winnipeg

Sun 6/7

5:42 pm-6:18 pm

1 stop24h 36m

$647

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/26

7:16 pm-11:29 pm

1 stop4h 13m

Winnipeg

Thu 7/16

11:15 am-9:40 am

2 stops22h 25m

$651

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 9/2

9:20 am-11:40 pm

2 stops14h 20m

Winnipeg

Sat 9/5

7:00 am-6:05 pm

2 stops11h 05m

$656

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/13

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Sun 5/17

11:40 am-2:35 pm

2 stops26h 55m

$722
Quickest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/13

9:22 am-5:15 pm

2 stops7h 53m

Winnipeg

Sun 5/17

11:55 am-5:56 pm

1 stop6h 01m

$735

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/6

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Sun 8/9

11:15 am-9:40 am

2 stops22h 25m

$760

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 9/18

6:45 pm-11:27 pm

1 stop4h 42m

Winnipeg

Sat 10/3

7:00 am-6:05 pm

2 stops11h 05m

$760
Cheapest one-way

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 6/8

10:25 am-5:58 pm

2 stops31h 33m

$207

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 6/28

6:00 am-8:00 pm

2 stops38h 00m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 17 resultsSorted by cheapest first
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 15h 33m. 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

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Portage la Prairie

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