S$254 Cheap Flights from Winnipeg to Chicago

View S$254 flight on Thu, 7 Aug, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Winnipeg to Chicago (YWG-ORD)

Prices were available within the past 7 days and start at S$254 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Winnipeg (YWG) to Chicago (ORD)

June is typically the cheapest month to fly

From S$322 - S$645 per traveller.

Graph displaying average flight prices per month

Winnipeg to Chicago route information
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Distance
1130 km
Average flight time
2 hours 31 mins

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.

Explore a world of travel with Expedia

*Available to Expedia members.