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MDW - YWG

$125 Find cheap flights from Chicago Midway Airport to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Winnipeg departing on 8/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 5/27
Mon 6/3

Search hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
In the last 7 days travelers have searched 43,623,357 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Winnipeg (MDW-YWG)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:53 am - 3:25 pmMDW-YWG
7h 32m1 stop
8:00 am - 8:49 pmYWG-MDW
12h 49m1 stop
$360
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Wed, May 29 - Thu, Jul 11
11:31 am - 12:44 amMDW-YWG
13h 13m1 stop
8:00 am - 2:41 pmYWG-MDW
6h 41m1 stop
$378
Find Deal
Fri, May 17 - Mon, May 20
8:40 am - 5:47 pmMDW-YWG
9h 07m2 stops
8:00 am - 5:12 pmYWG-MDW
9h 12m1 stop
$421
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Sun, May 26 - Sun, Jun 2
2:24 pm - 11:29 pmMDW-YWG
9h 05m1 stop
6:55 am - 12:43 pmYWG-MDW
5h 48m2 stops
$423Delta
Find Deal
Tue, Jun 11 - Thu, Jun 13
10:41 am - 3:25 pmMDW-YWG
28h 44m1 stop
8:00 am - 5:59 pmYWG-MDW
9h 59m1 stop
$453WestJet
Find Deal
Sat, Jun 8 - Wed, Jun 12
10:41 am - 3:25 pmMDW-YWG
28h 44m1 stop
7:30 am - 5:59 pmYWG-MDW
10h 29m2 stops
$459WestJet
Find Deal
Sat, Jun 8 - Wed, Jun 12
7:53 am - 3:25 pmMDW-YWG
7h 32m1 stop
8:00 am - 2:54 pmYWG-MDW
6h 54m1 stop
$468
Find Deal
Wed, May 29 - Wed, Jul 10
6:00 am - 9:12 pmMDW-YWG
15h 12m2 stops
7:30 am - 5:59 pmYWG-MDW
10h 29m2 stops
$471WestJet
Find Deal
Sat, Jun 8 - Wed, Jun 12
9:35 am - 9:12 pmMDW-YWG
11h 37m2 stops
6:55 am - 12:43 pmYWG-MDW
5h 48m2 stops
$498Delta
Find Deal
Tue, Jun 11 - Thu, Jun 13
9:32 am - 11:23 pmMDW-YWG
13h 51m2 stops
12:26 pm - 6:26 pmYWG-MDW
6h 00m1 stop
$525Delta
Find Deal
Tue, May 28 - Fri, Jul 12

Flights from Midway to Winnipeg - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Winnipeg, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Winnipeg is May, where tickets cost $381 on average. On the other hand, the most expensive months are December and August, where the average cost of tickets is $897 and $737 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Winnipeg?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Winnipeg, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Winnipeg, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Winnipeg?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Chicago Midway Airport to Winnipeg found on KAYAK was with WestJet for $237. Delta proposed a round-trip connection from $423 and WestJet from $453.

Good to know

Cheapest flight

$125
Flight from Chicago Midway Airport to Winnipeg

When to book flights from Midway to Winnipeg

Are your dates flexible? Find out the best times to travel from Midway to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Winnipeg flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Winnipeg was $125 for a one-way ticket and $360 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Winnipeg?

    Yes, you’ll need a passport to travel to Winnipeg from Chicago Midway Airport.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Winnipeg?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Winnipeg?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Winnipeg.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YWG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Chicago to Winnipeg

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Winnipeg found on KAYAK in the last 72 hours.
8/28Wed
1 stop
7h 55mMDW-YWG
$125
9/4Wed
1 stop
17h 43mMDW-YWG
$129
7/23Tue
1 stop
17h 38mMDW-YWG
$138
5/3Fri
1 stop
17h 06mMDW-YWG
$236
5/3Fri
2 stopsWestJet
16h 12mMDW-YWG
$237
7/23Tue
2 stopsDelta
10h 01mMDW-YWG
$251
5/28Tue
1 stop
10h 07mMDW-YWG
$252
5/4Sat
2 stopsWestJet
19h 54mMDW-YWG
$264
9/4Wed
2 stopsPorter Airlines
9h 52mMDW-YWG
$437
9/3Tue
2 stopsPorter Airlines
9h 52mMDW-YWG
$606

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Last minute flights from Midway to Winnipeg

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Winnipeg that are departing in the next 10 days.
4/30Tue
multi-stopWestJet
26h 40mMDW-YWG
5/2Thu
multi-stopWestJet
15h 20mYWG-MDW
$511
4/30Tue
multi-stopWestJet
17h 00mMDW-YWG
5/2Thu
multi-stopWestJet
15h 20mYWG-MDW
$954
4/30Tue
multi-stopDelta
6h 20mMDW-YWG
5/2Thu
multi-stopDelta
9h 01mYWG-MDW
$1,360

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Chicago Midway Airport - Winnipeg Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago Midway Airport

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