YWG - MDW

$212 Find Cheap Flights from Winnipeg to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Midway departing on 8/27. 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

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Everything you should know

Cheapest round-trip
$418
Multiple Airlines
Tue 9/29Sat 10/3
YWG - MDW • 1 stop
Cheapest one-way
$212
Multiple Airlines
Thu 8/27
YWG - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Winnipeg and Midway. You'll need at least 2 connections.
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Flight Deals

Cheap Flights from Winnipeg to Midway (YWG-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Midway 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 Winnipeg to Midway

Tue, Sep 29 - Sat, Oct 3
Multiple Airlines Logo
6:05 pm - 11:00 am
YWG
-
MDW
16h 55m
1 stop
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
$418Multiple Airlines
Tue, Sep 29 - Mon, Oct 5
Multiple Airlines Logo
6:05 pm - 11:00 am
YWG
-
MDW
16h 55m
1 stop
Multiple Airlines Logo
7:25 am - 10:10 pm
MDW
-
YWG
14h 45m
2 stops
$430Multiple Airlines
Tue, Sep 29 - Sat, Oct 3
Multiple Airlines Logo
6:05 pm - 11:00 am
YWG
-
MDW
16h 55m
1 stop
Multiple Airlines Logo
7:25 am - 10:10 pm
MDW
-
YWG
14h 45m
2 stops
$431Multiple Airlines
Tue, Sep 29 - Mon, Oct 5
Multiple Airlines Logo
6:05 pm - 11:00 am
YWG
-
MDW
16h 55m
1 stop
Multiple Airlines Logo
11:45 am - 8:45 pm
MDW
-
YWG
9h 00m
1 stop
$440Multiple Airlines
Thu, Aug 27 - Tue, Sep 1
Multiple Airlines Logo
9:05 pm - 10:55 am
YWG
-
MDW
13h 50m
2 stops
Multiple Airlines Logo
3:20 pm - 12:55 am
MDW
-
YWG
9h 35m
1 stop
$457Multiple Airlines
Thu, Oct 1 - Mon, Oct 5
Delta Logo
3:58 pm - 9:50 am
YWG
-
MDW
17h 52m
2 stops
Delta Logo
5:11 pm - 11:48 am
MDW
-
YWG
18h 37m
2 stops
$502Delta
Thu, Aug 27 - Tue, Sep 1
Multiple Airlines Logo
6:05 pm - 9:45 am
YWG
-
MDW
15h 40m
1 stop
Multiple Airlines Logo
11:45 am - 12:55 am
MDW
-
YWG
13h 10m
1 stop
$503Multiple Airlines
Thu, Aug 27 - Tue, Sep 1
Multiple Airlines Logo
4:15 pm - 9:45 am
YWG
-
MDW
17h 30m
2 stops
Multiple Airlines Logo
11:45 am - 12:55 am
MDW
-
YWG
13h 10m
1 stop
$504Multiple Airlines
Thu, Aug 27 - Tue, Sep 1
Multiple Airlines Logo
6:15 am - 2:35 pm
YWG
-
MDW
8h 20m
1 stop
Multiple Airlines Logo
11:45 am - 8:20 pm
MDW
-
YWG
8h 35m
1 stop
$508Multiple Airlines
Sat, Sep 19 - Wed, Sep 23
Delta Logo
12:46 pm - 6:19 pm
YWG
-
MDW
5h 33m
1 stop
Delta Logo
5:11 pm - 11:56 am
MDW
-
YWG
18h 45m
2 stops
$531Delta
Booking Insights

KAYAK's insights & trends for Winnipeg to Midway flights

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

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

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 Winnipeg to Chicago Midway Airport were found on Delta ($502) and WestJet ($576).

Find deals

Good to know

Cheapest flight

$212
Flight from Winnipeg to Chicago Midway Airport

When to book flights from Winnipeg to Midway

Are your dates flexible? Find out the best times to travel from Winnipeg to Midway 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 Winnipeg to Chicago Midway Airport flights

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

    In the last 5 days, the lowest price for a flight from Winnipeg to Chicago Midway Airport was $212 for a one-way ticket and $418 for a round-trip.

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

    A passport is required to fly from Winnipeg to Chicago Midway Airport.

  • Which airports will I be using when flying from Winnipeg to Chicago Midway Airport?

    Winnipeg and Chicago Midway Airport are both served by 1 main airport. You will leave Winnipeg from Winnipeg and will be arriving at Chicago Midway.

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

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

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

    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 Winnipeg to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Winnipeg 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 Winnipeg to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Winnipeg with another airline. Booking your flights between Winnipeg and MDW 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 Winnipeg to Chicago Midway Airport?

    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 Chicago Midway Airport from Winnipeg 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 Winnipeg to Midway

Information on your arrival and departure airports

Winnipeg (YWG)
Midway (MDW)