YWG - MDW

$196 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 7/13. 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

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

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Winnipeg to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Winnipeg to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Logo
6:30 am - 11:18 pmYWG-MDW
16h 48m2 stops
Logo
6:30 am - 4:28 pmMDW-YWG
9h 58m1 stop
$366
Find Deal
Thu, Jun 5 - Mon, Jun 9
Delta Logo
12:26 pm - 5:12 pmYWG-MDW
4h 46m1 stop
Delta Logo
9:21 am - 4:52 pmMDW-YWG
7h 31m1 stop
$405Delta
Find Deal
Sat, Jun 14 - Sat, Jun 21
Porter Airlines Logo
11:45 am - 8:45 amYWG-MDW
21h 00m2 stops
Porter Airlines Logo
9:40 am - 10:46 pmMDW-YWG
13h 06m2 stops
$412Porter Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
WestJet Logo
5:35 pm - 5:45 pmYWG-MDW
24h 10m1 stop
WestJet Logo
7:21 pm - 8:12 pmMDW-YWG
24h 51m1 stop
$424WestJet
Find Deal
Thu, Jun 5 - Mon, Jun 9
Porter Airlines Logo
6:55 pm - 4:54 pmYWG-MDW
21h 59m1 stop
Porter Airlines Logo
9:40 am - 12:25 pmMDW-YWG
26h 45m1 stop
$445Porter Airlines
Find Deal
Thu, May 29 - Sun, Jun 1
Delta Logo
6:45 am - 12:29 pmYWG-MDW
5h 44m2 stops
Delta Logo
1:46 pm - 8:10 pmMDW-YWG
6h 24m1 stop
$454Delta
Find Deal
Sat, Jul 12 - Thu, Jul 17
WestJet Logo
8:35 am - 1:06 pmYWG-MDW
4h 31m1 stop
WestJet Logo
7:21 pm - 11:25 pmMDW-YWG
4h 04m1 stop
$462WestJet
Find Deal
Sat, Jul 12 - Wed, Jul 16
Logo
11:45 am - 8:45 amYWG-MDW
21h 00m2 stops
Logo
5:20 pm - 10:46 pmMDW-YWG
29h 26m2 stops
$472
Find Deal
Mon, Jun 9 - Tue, Jun 10
WestJet Logo
8:30 am - 1:15 pmYWG-MDW
4h 45m1 stop
WestJet Logo
7:25 pm - 11:25 pmMDW-YWG
4h 00m1 stop
$486WestJet
Find Deal
Sat, May 24 - Sun, Jun 1
WestJet Logo
9:00 am - 9:41 pmYWG-MDW
12h 41m1 stop
WestJet Logo
1:46 pm - 4:50 pmMDW-YWG
27h 04m1 stop
$493WestJet
Find Deal
Mon, Jul 7 - Fri, Jul 11
Useful Info

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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Winnipeg to Chicago Midway Airport were found on Delta ($405) and Porter Airlines ($412).

Find deals

Good to know

Cheapest flight$196
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 $196 for a one-way ticket and $366 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.

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

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

  • 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

Midway (MDW)
Winnipeg (YWG)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.