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$140+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Apr 13 — Apr 201
Mon 4/13
Mon 4/20
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 March 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Fri 4/246:00 am
MDW
-
YWG
1 stop9h 09m
Multiple Airlines
Fri 5/19:05 pm
YWG
-
MDW
2 stops21h 32m
Multiple Airlines
Deal found 3/9$336
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Fri 4/104:05 pm
MDW
-
YWG
1 stop18h 47m
Multiple Airlines
Tue 4/148:00 am
YWG
-
MDW
2 stops11h 31m
Multiple Airlines
Deal found 3/9$409
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/711:00 am
MDW
-
YWG
2 stops35h 40m
Multiple Airlines
Thu 4/168:05 pm
YWG
-
MDW
1 stop19h 15m
Multiple Airlines
Deal found 3/13$460
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Sun 9/68:05 am
MDW
-
YWG
2 stops14h 05m
Multiple Airlines
Sat 9/1212:40 pm
YWG
-
MDW
1 stop5h 25m
Multiple Airlines
Deal found 3/9$519
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 6/113:20 pm
MDW
-
YWG
1 stop9h 35m
Multiple Airlines
Sun 6/216:05 pm
YWG
-
MDW
1 stop20h 30m
Multiple Airlines
Deal found 3/13$529
This Justfly.com deal was found by Cheapflights users on 3/9. 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.
Tue 6/99:30 am
MDW
-
YWG
2 stops15h 25m
WestJet
Fri 6/124:09 pm
YWG
-
MDW
1 stop25h 56m
WestJet
Deal found 3/9$559
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:20 pm
MDW
-
YWG
1 stop17h 20m
Multiple Airlines
Mon 8/179:05 pm
YWG
-
MDW
2 stops23h 01m
Multiple Airlines
Deal found 3/12$580

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 March 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$336
(Kiwi.com)

One-way from

$140
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$712
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. 23% potential increase in price ($184 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 March 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 March 14, 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

Fri 6/5

9:23 am-12:55 am

2 stops15h 32m

Winnipeg

Sun 6/7

6:15 am-6:31 pm

2 stops12h 16m

$687

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/23

10:25 am-8:20 pm

1 stop9h 55m

Winnipeg

Fri 7/31

4:15 pm-9:40 am

2 stops17h 25m

$734
Quickest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 5/11

9:23 am-4:51 pm

1 stop7h 28m

Winnipeg

Mon 6/1

12:26 pm-5:56 pm

1 stop5h 30m

$736

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 4/11

7:20 pm-11:35 pm

1 stop4h 15m

Winnipeg

Tue 4/14

12:55 pm-6:36 pm

2 stops29h 41m

$743

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/24

9:20 am-9:45 am

2 stops24h 25m

Winnipeg

Sun 6/28

10:45 am-6:31 pm

2 stops7h 46m

$781

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 7/8

9:20 am-4:54 pm

1 stop7h 34m

Winnipeg

Tue 7/14

12:40 pm-6:05 pm

1 stop5h 25m

$784
Cheapest one-way

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 8/31

8:05 am-11:40 pm

2 stops15h 35m

$223

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/15

11:00 am-11:13 am

2 stops24h 13m

$256
Quickest one-way

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/27

6:05 am-3:09 pm

1 stop9h 04m

$256

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 9/5

9:11 pm-10:10 pm

3 stops24h 59m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 15 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 and Delta fly from Chicago Midway Airport to Winnipeg in about 7h 28m. The time it takes to get you to your destination can typically vary by up to 8h 04m. The distance between Chicago Midway Airport and Winnipeg is about 722 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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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