HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$75+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$290
(Kiwi.com)

One-way from

$75
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$574
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. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find 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 octubre 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
dom. 11/236:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
mié. 11/267:30 amYWG - MDW
1 stop15h 13mMultiple Airlines
Deal found 10/28$290
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
jue. 11/208:41 pmMDW - YWG
2 stops18h 26mMultiple Airlines
lun. 11/248:05 pmYWG - MDW
1 stop14h 00mMultiple Airlines
Deal found 10/26$301
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
vie. 11/216:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
dom. 11/2312:40 pmYWG - MDW
2 stops26h 08mMultiple Airlines
Deal found 10/26$313
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
jue. 11/208:41 pmMDW - YWG
2 stops18h 26mMultiple Airlines
lun. 12/18:20 pmYWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 10/26$347
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
jue. 12/117:23 pmMDW - YWG
1 stop19h 44mMultiple Airlines
jue. 12/185:00 amYWG - MDW
2 stops13h 00mMultiple Airlines
Deal found 10/27$351
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sáb. 11/2212:45 pmMDW - YWG
1 stop11h 57mMultiple Airlines
mié. 11/267:30 amYWG - MDW
1 stop15h 13mMultiple Airlines
Deal found 10/28$363
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
dom. 11/236:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
mar. 11/258:05 pmYWG - MDW
1 stop14h 00mMultiple Airlines
Deal found 10/28$407

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 octubre 28, 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. 11/23

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

mié. 11/26

7:30 am-10:43 pm

1 stop15h 13m

$290

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 11/20

8:41 pm-3:07 pm

2 stops18h 26m

Winnipeg

lun. 11/24

8:05 pm-10:05 am

1 stop14h 00m

$301

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 11/21

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

dom. 11/23

12:40 pm-2:48 pm

2 stops26h 08m

$313

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 12/11

7:23 pm-3:07 pm

1 stop19h 44m

Winnipeg

jue. 12/18

5:00 am-6:00 pm

2 stops13h 00m

$351

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 11/22

12:45 pm-12:42 am

1 stop11h 57m

Winnipeg

mié. 11/26

7:30 am-10:43 pm

1 stop15h 13m

$363

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 11/20

11:00 am-12:35 am

1 stop13h 35m

Winnipeg

lun. 12/1

8:20 pm-10:05 am

1 stop13h 45m

$400

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

dom. 11/23

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

mar. 11/25

8:05 pm-10:05 am

1 stop14h 00m

$407

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

dom. 11/23

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

dom. 11/30

8:05 pm-3:20 pm

1 stop19h 15m

$410

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

lun. 11/24

4:15 pm-11:35 am

1 stop19h 20m

Winnipeg

lun. 12/1

8:20 pm-10:05 am

1 stop13h 45m

$426

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 12/11

7:23 pm-3:07 pm

1 stop19h 44m

$75

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 13 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 October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.