HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$127+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$314
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$566
From Chicago Midway to Winnipeg
Search Deals
One-way flight from Chicago Midway to Winnipeg
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 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 June 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 June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:15 amMDW - YWG
1 stop10h 07mMultiple Airlines
Thu 9/259:00 amYWG - MDW
1 stop9h 18mMultiple Airlines
Deal found 6/11$314
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:30 amMDW - YWG
2 stops14h 02mDelta
Tue 9/306:40 amYWG - MDW
2 stops15h 04mDelta
Deal found 6/11$404
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/189:40 amMDW - YWG
2 stops13h 06mPorter Airlines
Sun 7/206:55 pmYWG - MDW
1 stop13h 50mPorter Airlines
Deal found 6/11$543
This oojo deal was found by Cheapflights users on 6/12. 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.
Tue 10/289:20 amMDW - YWG
2 stops10h 15mWestJet
Fri 11/75:00 amYWG - MDW
2 stops16h 44mWestJet
Deal found 6/12$596

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 June 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

Mon 9/22

6:15 am-4:22 pm

1 stop10h 07m

Winnipeg

Thu 9/25

9:00 am-6:18 pm

1 stop9h 18m

$314

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 9/22

9:30 am-11:32 pm

2 stops14h 02m

Winnipeg

Tue 9/30

6:40 am-9:44 pm

2 stops15h 04m

$404

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 7/18

9:40 am-10:46 pm

2 stops13h 06m

Winnipeg

Sun 7/20

6:55 pm-8:45 am

1 stop13h 50m

$543

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 10/28

9:20 am-7:35 pm

2 stops10h 15m

Winnipeg

Fri 11/7

5:00 am-9:44 pm

2 stops16h 44m

$596

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/15

11:39 am-12:31 am

2 stops12h 52m

$127

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 10/15

6:00 am-4:22 pm

1 stop10h 22m

$206

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 9/4

9:15 am-8:46 pm

2 stops11h 31m

$217

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/15

1:09 pm-11:11 pm

2 stops10h 02m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Winnipeg

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated June 12, 2025.
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Winnipeg one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $206. Porter Airlines flights start at $217 while deals on WestJet start at $270 one-way.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Winnipeg (average of $358). Flying from Chicago Midway Airport to Winnipeg in December is currently the most expensive (average of $497). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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.