S$250 Cheap Flights from Winnipeg to Chicago

View S$250 flight on Thu, 21 Aug, 2025Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Winnipeg to Chicago (YWG-ORD)

Prices were available within the past 7 days and start at S$250 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Winnipeg to Chicago route information
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Distance
1130 km

Flights from Winnipeg to Chicago

When looking for plane tickets from Winnipeg to Chicago, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to Chicago. Look for YWG to ORD airfare with the assurance that you have the largest online travel agency working for you.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Winnipeg Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Winnipeg to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Winnipeg to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from Winnipeg Airport to ORD?
Round-trip flights from Winnipeg Airport to ORD start from . This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book today so you don’t miss out. 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 O'Hare Airport?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from YWG to O'Hare Intl. Airport (ORD) 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 O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Winnipeg Airport to O'Hare Airport?
With a flight distance of 1,150 kilometres, it’s just a hop from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O’Hare Airport. It might be a quick journey, but it’s still worth bringing a book to read.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport?
If you want to fly straight from Winnipeg Airport to O’Hare Airport, you’ll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices are constantly going up and down, so not always. While last-minute deals between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and ORD are of course possible, it’s also a good idea to keep a close eye on prices well before you fly. In fact, some carriers release their prices up to a year ahead of the departure date. Expedia is constantly updating the biggest airfare bargains around, so keep checking and be ready to pounce when the price is low.

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