$197 Cheap Flights from Chicago (MDW) to Winnipeg (YWG)

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Cheap Flights from Chicago to Winnipeg (MDW-YWG)

Prices were available within the past 7 days and start at $197 for one-way flights and $429 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
WestJet
Delta
Delta
Delta
Delta
Delta
Delta
WestJet
Delta
Flights from Chicago (MDW) to Winnipeg (YWG)
Origin airport
Midway Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$428
Distance
721 mi

Chicago to Winnipeg Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Winnipeg offer the perfect respite. Not only does exploring Winnipeg provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Winnipeg may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Winnipeg are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Winnipeg more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Winnipeg is $197 now!

Frequently asked questions

How much is a one-way flight from MDW to Winnipeg Airport?
Plan your next trip with Expedia and you could bag one-way Chicago flights to Winnipeg from $170. This was the best fare found for this particular journey departing during the next three months — an WestJet flight, taking off from Chicago Airport on June 15 2024 and landing at YWG. The price was last updated on May 23 2024 and has not changed since. Eager to pick up your own bargain? The best deals are only a click of a button away.
Is it cheaper to buy a plane ticket from Chicago Airport to YWG last minute?
When it’s time to book your flights, being prepared pays dividends. While you may be able to score a deal on a MDW to YWG flight at the last minute, tickets usually don’t get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international flights it’s between three and four months.
What is the cheapest airline flying from Midway Airport to Winnipeg Airport in the next 90 days?
With fares starting from $170 for a flight from Chicago to Winnipeg, WestJet is the cheapest airline found on Expedia. This price is based on airfares found on Expedia with a departure date within the next 90 days and was updated on May 23 2024 and has not changed since. The flight jets off from MDW on June 15 2024 and arrives at YWG.
What's the cheapest price for a flight from Midway Intl. Airport (MDW) to YWG next month?
The cheapest ticket for a one-way flight from Chicago to Winnipeg over the next month is $170. If you’re looking to travel soon, now’s the time to book. This price was found after looking at all available flights on Expedia with a departure date within the next 30 days. This airfare is for a one-way WestJet flight departing MDW on June 15 2024 and landing at Winnipeg James Armstrong Richardson Intl. Airport (YWG). This price was updated on May 23 2024 and has not changed since.
What airports do you fly into for Winnipeg from Chicago?
Chicago to Winnipeg flights touch down at Winnipeg James Armstrong Richardson Intl. Airport (YWG). Drop your bags at your hotel and then head out and tick off some of the city’s noteworthy attractions, such as University of Manitoba and University of Winnipeg. The airport is about 6 mi northwest of downtown Winnipeg.
Can I change the date of my flight from Midway Airport to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Easily make changes to your MDW to Winnipeg James Armstrong Richardson Intl. Airport (YWG) ticket via the Expedia Trips portal. Before making any amendments, read through the rules and conditions in your itinerary to learn what the airline will allow you to do and if change fees apply. Some carriers charge a change fee per person, on top of any difference in prices. However, if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also stop by our Customer Service portal for further information and to connect with our Virtual Agent.
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