YWG - MDW

$211 Find Cheap Flights from Winnipeg to Chicago Midway Airport

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 6/16. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Chicago, 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 Winnipeg to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$456
Multiple Airlines
Fri 6/26Fri 7/3
YWG - MDW • 1 stop
Cheapest one-way
$211
Multiple Airlines
Tue 6/16
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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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Fri, Jun 26 - Fri, Jul 3
Multiple Airlines Logo
6:15 am - 2:35 pm
YWG
-
MDW
8h 20m
1 stop
Multiple Airlines Logo
10:25 am - 7:25 pm
MDW
-
YWG
9h 00m
1 stop
$456Multiple Airlines
Sun, Jul 12 - Wed, Jul 15
Multiple Airlines Logo
9:25 am - 2:35 pm
YWG
-
MDW
29h 10m
1 stop
Multiple Airlines Logo
10:25 am - 7:25 pm
MDW
-
YWG
9h 00m
1 stop
$463Multiple Airlines
Thu, Jun 25 - Thu, Jul 2
Multiple Airlines Logo
6:05 pm - 9:40 am
YWG
-
MDW
15h 35m
1 stop
Multiple Airlines Logo
3:20 pm - 8:40 am
MDW
-
YWG
17h 20m
1 stop
$468Multiple Airlines
Sun, Jul 12 - Wed, Jul 15
Multiple Airlines Logo
8:50 pm - 2:35 pm
YWG
-
MDW
17h 45m
1 stop
Multiple Airlines Logo
3:20 pm - 8:40 am
MDW
-
YWG
17h 20m
1 stop
$484Multiple Airlines
Sun, Jul 12 - Wed, Jul 15
Multiple Airlines Logo
10:30 pm - 9:40 am
YWG
-
MDW
35h 10m
2 stops
Multiple Airlines Logo
10:25 am - 7:25 pm
MDW
-
YWG
9h 00m
1 stop
$501Multiple Airlines
Tue, Oct 20 - Thu, Oct 22
Delta Logo
6:35 am - 9:45 pm
YWG
-
MDW
15h 10m
2 stops
Delta Logo
6:00 am - 11:34 pm
MDW
-
YWG
17h 34m
2 stops
$506Delta
Sun, Jul 12 - Wed, Jul 15
Multiple Airlines Logo
8:50 pm - 2:35 pm
YWG
-
MDW
17h 45m
1 stop
Multiple Airlines Logo
3:20 pm - 8:40 am
MDW
-
YWG
17h 20m
1 stop
$521Multiple Airlines
Tue, Oct 20 - Thu, Oct 22
Delta Logo
6:35 am - 9:45 pm
YWG
-
MDW
15h 10m
2 stops
Delta Logo
6:00 am - 11:34 pm
MDW
-
YWG
17h 34m
2 stops
$528Delta
Sun, Jul 12 - Wed, Jul 15
Multiple Airlines Logo
10:30 pm - 9:40 am
YWG
-
MDW
35h 10m
2 stops
Multiple Airlines Logo
10:25 am - 7:25 pm
MDW
-
YWG
9h 00m
1 stop
$531Multiple Airlines
Fri, Jun 26 - Fri, Jul 3
Multiple Airlines Logo
7:00 am - 9:14 am
YWG
-
MDW
26h 14m
2 stops
Multiple Airlines Logo
10:25 am - 7:25 pm
MDW
-
YWG
9h 00m
1 stop
$554Multiple Airlines
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 3 days.

In the past 3 days, the cheapest round-trip tickets from Winnipeg to Chicago Midway Airport were found on Delta ($506) and Porter Airlines ($527).

Find deals

Good to know

Cheapest flight$211
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 3 days, the lowest price for a flight from Winnipeg to Chicago Midway Airport was $211 for a one-way ticket and $456 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)