￥36,270 Cheap Flights from Winnipeg (YWG) to Chicago (MDW)

View ￥36,270 flight on Thu, Dec 18, 2025Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago Midway Airport (MDW)

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Cheap Flights from Winnipeg to Chicago (YWG-MDW)

Prices were available within the past 7 days and start at ￥36,270 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from Winnipeg (YWG) to Chicago (MDW)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Midway Intl.
Distance
1154 km

Winnipeg to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Winnipeg to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with YWG to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Winnipeg for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from YWG to Chicago Airport?
Based on airfares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Midway Intl. Airport (MDW) start from . Book now to secure the best price for your adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YWG to MDW?
Every airline has its own set of terms and conditions. If you decide to cancel your trip, head to our Customer Service Portal.
How do I find cheap flights from YWG to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Winnipeg James Armstrong Richardson Intl. Airport (YWG) to MDW flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago Airport?
Lasting around 4 hours and 4 minutes, the flight between Winnipeg Airport and Midway Airport is a good opportunity to do some last-minute trip planning. Why not use this time to fine tune your itinerary for Chicago?
How far is the flight from YWG to Midway Intl. Airport (MDW)?
You might not get through a whole movie on this flight — it's only 1,150 kilometers from Winnipeg to Chicago. Find your seat, order a drink and you'll be there in next to no time.
Which airlines fly direct from Winnipeg Airport to Chicago Airport?
You won't find any airlines flying directly between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Midway Airport, so be ready to make at least one stop on your journey. A layover can be a welcome way to break up a trip!
Are Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Flight prices fluctuate, so not always. While last-minute deals between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Midway Intl. Airport (MDW) are possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some air carriers advertise their prices up to a year ahead of the departure date. Expedia is constantly updating the best airfare bargains around, so check back often and be ready to lock in your seat when the price dips.

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