MDW - YWG

$103 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 1/31. 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
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Everything you should know

Cheapest round-trip
$253
Multiple Airlines
Fri 1/16Thu 1/22
MDW - YWG • 1 stop
Cheapest one-way
$103
Multiple Airlines
Sat 1/31
MDW - YWG • 1 stop
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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 Winnipeg!
Flight Deals
Useful Info
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

Fri, Jan 16 - Thu, Jan 22
Multiple Airlines Logo
6:10 am - 3:07 pm
MDW
-
YWG
8h 57m1 stop
Multiple Airlines Logo
9:00 pm - 11:45 am
YWG
-
MDW
14h 45m2 stops
$253Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
6:25 am - 12:40 am
MDW
-
YWG
18h 15m2 stops
Multiple Airlines Logo
7:30 am - 7:59 pm
YWG
-
MDW
12h 29m1 stop
$267Multiple Airlines
Thu, Jan 22 - Sat, Jan 24
Multiple Airlines Logo
6:20 am - 12:41 am
MDW
-
YWG
18h 21m2 stops
Multiple Airlines Logo
8:20 pm - 3:20 pm
YWG
-
MDW
19h 00m1 stop
$292Multiple Airlines
Wed, Mar 11 - Fri, Mar 20
Multiple Airlines Logo
6:00 am - 3:09 pm
MDW
-
YWG
9h 09m1 stop
Multiple Airlines Logo
5:05 pm - 10:45 pm
YWG
-
MDW
29h 40m1 stop
$310Multiple Airlines
Thu, Jan 22 - Sat, Jan 24
Multiple Airlines Logo
11:05 am - 12:42 am
MDW
-
YWG
13h 37m1 stop
Multiple Airlines Logo
9:00 pm - 11:45 am
YWG
-
MDW
14h 45m2 stops
$330Multiple Airlines
Thu, Jan 22 - Sat, Jan 24
Multiple Airlines Logo
11:05 am - 12:42 am
MDW
-
YWG
13h 37m1 stop
Multiple Airlines Logo
8:20 pm - 3:20 pm
YWG
-
MDW
19h 00m1 stop
$350Multiple Airlines
Mon, Jan 19 - Fri, Jan 23
Multiple Airlines Logo
12:57 pm - 12:43 am
MDW
-
YWG
11h 46m1 stop
Multiple Airlines Logo
8:05 pm - 8:52 am
YWG
-
MDW
12h 47m2 stops
$359Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
5:16 pm - 3:09 pm
MDW
-
YWG
21h 53m1 stop
Multiple Airlines Logo
7:30 am - 7:59 pm
YWG
-
MDW
12h 29m1 stop
$362Multiple Airlines
Mon, Jan 19 - Fri, Jan 23
Multiple Airlines Logo
12:57 pm - 12:43 am
MDW
-
YWG
11h 46m1 stop
Multiple Airlines Logo
7:30 am - 10:19 pm
YWG
-
MDW
14h 49m1 stop
$368Multiple Airlines
Thu, Jan 22 - Sat, Jan 24
Multiple Airlines Logo
11:05 am - 12:42 am
MDW
-
YWG
13h 37m1 stop
Multiple Airlines Logo
8:20 pm - 3:20 pm
YWG
-
MDW
19h 00m1 stop
$376Multiple Airlines
Useful Info

Good to know

Cheapest flight$103
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 $103 for a one-way ticket and $253 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)