MDW - YWG

$162 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 8/11. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$397
Multiple Airlines
Do 7/30Sa 8/1
MDW - YWG • 2 stops
Cheapest one-way
$162
Multiple Airlines
Di 8/11
MDW - YWG • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Midway and Winnipeg. You'll need at least 1 connection.
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We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Winnipeg

Do, Jul 30 - Sa, Aug 1
Multiple Airlines Logo
3:20 pm - 2:05 pm
MDW
-
YWG
22h 45m
2 stops
Multiple Airlines Logo
5:10 pm - 9:40 am
YWG
-
MDW
16h 30m
1 stop
$397Multiple Airlines
Do, Jul 30 - Sa, Aug 1
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
Multiple Airlines Logo
5:10 pm - 9:40 am
YWG
-
MDW
16h 30m
1 stop
$406Multiple Airlines
Sa, Aug 1 - Mi, Aug 5
Multiple Airlines Logo
10:20 am - 12:00 pm
MDW
-
YWG
25h 40m
2 stops
Multiple Airlines Logo
6:05 pm - 9:40 am
YWG
-
MDW
15h 35m
1 stop
$433Multiple Airlines
Sa, Aug 1 - Mi, Aug 5
Multiple Airlines Logo
10:20 am - 11:19 am
MDW
-
YWG
24h 59m
1 stop
Multiple Airlines Logo
6:05 pm - 9:40 am
YWG
-
MDW
15h 35m
1 stop
$449Multiple Airlines
Fr, Aug 28 - Di, Sep 8
Multiple Airlines Logo
3:15 pm - 9:45 am
MDW
-
YWG
18h 30m
1 stop
Multiple Airlines Logo
9:05 pm - 10:58 am
YWG
-
MDW
13h 53m
2 stops
$506Multiple Airlines
Sa, Aug 1 - Mi, Aug 5
Multiple Airlines Logo
10:20 am - 9:20 am
MDW
-
YWG
23h 00m
2 stops
Multiple Airlines Logo
9:05 pm - 2:35 pm
YWG
-
MDW
17h 30m
2 stops
$534Multiple Airlines
Do, Jul 30 - Sa, Aug 1
Multiple Airlines Logo
3:20 pm - 9:20 am
MDW
-
YWG
18h 00m
2 stops
Multiple Airlines Logo
2:55 pm - 9:40 am
YWG
-
MDW
18h 45m
2 stops
$560Multiple Airlines
Di, Jul 14 - Di, Jul 21
Porter Airlines Logo
10:25 am - 10:43 am
MDW
-
YWG
24h 18m
2 stops
Porter Airlines Logo
4:15 pm - 9:40 am
YWG
-
MDW
17h 25m
2 stops
$587Porter Airlines
Sa, Jul 18 - Sa, Jul 25
Multiple Airlines Logo
6:55 pm - 11:29 pm
MDW
-
YWG
4h 34m
1 stop
Multiple Airlines Logo
11:15 am - 9:40 am
YWG
-
MDW
22h 25m
2 stops
$599Multiple Airlines
Sa, Aug 1 - Mi, Aug 5
Multiple Airlines Logo
9:19 am - 12:00 pm
MDW
-
YWG
26h 41m
3 stops
Multiple Airlines Logo
9:05 pm - 2:35 pm
YWG
-
MDW
17h 30m
2 stops
$606Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to Winnipeg flights

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.

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

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Winnipeg were found on Porter Airlines ($587) and WestJet ($687).

Find deals

Good to know

Cheapest flight$162
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 5 days, the lowest price for a flight from Chicago Midway Airport to Winnipeg was $162 for a one-way ticket and $397 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.

  • 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.

Everything you need to know for your flight from Midway to Winnipeg

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Winnipeg (YWG)