YWG to MDW (Winnipeg to Chicago) Flights

Last Minute Flights from YWG to MDW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
YWGChicagoJuly 18 to July 26$838
*Prices include taxes and fees

Cheapest YWG to MDW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
YWGChicagoJuly 25 to August 9$415
YWGChicagoOctober 18 to October 28$456
YWGChicagoOctober 18 to October 28$476
YWGChicagoOctober 18 to October 28$480
*Prices include taxes and fees
YWG to MDW Flight Details
Origin airport
Winnipeg James Armstrong Richardson Intl.
Origin airport IATA code
YWG
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
721 mi

Frequently asked questions

What airlines fly direct from Winnipeg Airport to MDW?
Currently, you can't fly straight between these airports. You'll have to book a flight with one or more stops to journey from Winnipeg Airport to MDW.
How many flights are there from YWG to MDW?
There are around 3 daily flights from Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) to Chicago, IL (MDW-Midway Intl.), so you have no shortage of ways to get to Chicago. Just pick a date and time that matches your schedule and lock in your fare.
How long does it take to fly from Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) to Chicago, IL (MDW-Midway Intl.)?
Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) to Chicago, IL (MDW-Midway Intl.) takes on average 3 hours and 59 minutes. That's an ideal length of time to watch a popular new series, get lost in a podcast or catch some z's.
What is the flight distance from Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) to Chicago, IL (MDW-Midway Intl.)?
With a distance of just 720 miles (1,150 1), the short-haul journey between Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) and Chicago, IL (MDW-Midway Intl.) is a breezy one. Spend your journey daydreaming about what you plan to do and see once you touch down in Chicago.
How many morning flights are there from YWG to MDW?
Every week, 12 flights jet off from YWG to MDW before noon. Delta Air Lines (DL) operates 7 of these, with the earliest leaving at 6:55AM.
How many afternoon flights are there from YWG to MDW?
With 12 afternoon and evening flights every week from YWG to MDW, there's no need to stress about getting up with the roosters. Delta Air Lines (DL) has 12 weekly services after midday, with its earliest departure taxiing from the gate at 12:22PM.
What is the earliest departure time out of Winnipeg to Chicago?
The earliest flight jets off from YWG at 6:55AM and touches down at 6:07PM at MDW. Make sure you allow yourself lots of time in the morning to easily make it to the airport.
What is the latest departure time out of Winnipeg to Chicago?
Reserve a seat on the 5:35PM flight from YWG, landing at MDW at 6:07PM, and allow yourself time to take care of any last-minute vacation preparations. This is the latest flight you can get on this route.
What is the average price from Winnipeg to Chicago?
Round-trip journeys for this route begin from around $415. When you're ready to take to the skies, we'll help you land the best price in town. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Winnipeg to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Winnipeg to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from YWG to MDW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Winnipeg to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.