$139 Cheap Flights from Chicago (ORD) to Winnipeg (YWG)

View $139 flight on Mon, Dec 15, 2025Opens in a new window

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

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Cheap Flights from Chicago to Winnipeg (ORD-YWG)

Prices were available within the past 7 days and start at $139 for one-way flights and $327 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Mon, Feb 2 - Mon, Feb 9
ORD
Chicago
YWG
Winnipeg
$327 Roundtrip, found 1 day ago
$327
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Feb 2 from Chicago to Winnipeg, returning Mon, Feb 9, priced at $327 found 1 day ago
WestJet
Mon, Feb 2 - Mon, Feb 9
ORD
Chicago
YWG
Winnipeg
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Feb 2 from Chicago to Winnipeg, returning Mon, Feb 9, priced at $353 found 1 day ago
WestJet
Fri, Feb 20 - Mon, Feb 23
ORD
Chicago
YWG
Winnipeg
$353 Roundtrip, found 13 hours ago
$353
Roundtrip
found 13 hours ago
Select WestJet flight, departing Fri, Feb 20 from Chicago to Winnipeg, returning Mon, Feb 23, priced at $353 found 13 hours ago
Delta
Wed, Nov 19 - Mon, Nov 24
ORD
Chicago
YWG
Winnipeg
$357 Roundtrip, found 3 days ago
$357
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Nov 19 from Chicago to Winnipeg, returning Mon, Nov 24, priced at $357 found 3 days ago
Air Canada
Wed, Nov 12 - Thu, Nov 13
ORD
Chicago
YWG
Winnipeg
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Nov 12 from Chicago to Winnipeg, returning Thu, Nov 13, priced at $363 found 1 day ago
WestJet
Mon, Jan 19 - Thu, Jan 29
ORD
Chicago
YWG
Winnipeg
$379 Roundtrip, found 4 days ago
$379
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Jan 19 from Chicago to Winnipeg, returning Thu, Jan 29, priced at $379 found 4 days ago
Air Canada
Mon, Jan 19 - Fri, Jan 30
ORD
Chicago
YWG
Winnipeg
$387 Roundtrip, found 4 days ago
$387
Roundtrip
found 4 days ago
Select Air Canada flight, departing Mon, Jan 19 from Chicago to Winnipeg, returning Fri, Jan 30, priced at $387 found 4 days ago
WestJet
Mon, Jan 5 - Fri, Jan 9
ORD
Chicago
YWG
Winnipeg
$393 Roundtrip, found 4 days ago
$393
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Jan 5 from Chicago to Winnipeg, returning Fri, Jan 9, priced at $393 found 4 days ago
United
Fri, Jan 2 - Sun, Jan 11
ORD
Chicago
YWG
Winnipeg
$583 Roundtrip, found 21 hours ago
$583
Roundtrip
found 21 hours ago
Select United flight, departing Fri, Jan 2 from Chicago to Winnipeg, returning Sun, Jan 11, priced at $583 found 21 hours ago
Porter Airlines
Fri, Feb 20 - Mon, Feb 23
ORD
Chicago
YWG
Winnipeg
$711 Roundtrip, found 13 hours ago
$711
Roundtrip
found 13 hours ago
Select Porter Airlines flight, departing Fri, Feb 20 from Chicago to Winnipeg, returning Mon, Feb 23, priced at $711 found 13 hours ago

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

October is typically the cheapest month to fly

From $243 - $1,190 per traveler.

Alternative airports near Winnipeg

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Winnipeg Intl. YWG. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $569
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $569

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) cost?
Lock in a cheap one-way flight from $139 or cheap return flight from $327 from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Planning your trip for February is a good way to save, as it's the cheapest month for flights between ORD and YWG. You'll often find the lowest prices during the off-season.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Fly directly from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) on a United Airlines flight.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To find the cheapest airline that'll fly you from ORD to YWG, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
On average, there is just 1 direct flight leaving from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) every day. If this doesn't fit your travel plans, think about flights with layovers. Simply filter your search on Expedia to include one stop or more to find the next best option.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Flights between ORD and YWG tend to be busiest at 12 PM. For a quieter trip and possibly cheaper tickets, choose a time when demand is lower.
What day of the week has the most flights from ORD to YWG?
Sunday has the most flights from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). Consider traveling on this day and you'll have a greater chance of finding a departure that fits your itinerary.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Take the earliest flight at around 12:56PM UTC-6, leaving from O'Hare Intl. Airport (ORD). You'll be flying for approximately 2h 32m, reaching Winnipeg James Armstrong Richardson Intl. Airport (YWG) at approximately 3:28PM UTC-6.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
The average flight time from ORD to YWG is 2 hours and 32 minutes, covering a total distance of 710 mi.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To land at Winnipeg James Armstrong Richardson Intl. Airport (YWG) on schedule, opt for a flight that leaves from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Winnipeg from O'Hare Intl. Airport (ORD)?
If you're flying on a direct flight from O'Hare Intl. Airport (ORD) to Winnipeg, Winnipeg James Armstrong Richardson Intl. Airport (YWG) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) last-minute?
Booking your flight from ORD to YWG just before your trip is usually more expensive. However, if you're flexible with your departure dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book an ORD to YWG flight and hotel package?
You can save money by securing an ORD to YWG flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've chosen your preferred accommodations and flights, you can add extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Typically, you can modify or cancel your ORD to YWG flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you'd like more details, head to our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Air Canada, Delta, Porter Airlines, United, WestJet
Roundtrip price
$326
Distance
706 mi
Average flight time
2 hours 35 mins

Book with confidence

Chicago to Winnipeg Flights

The cheapest times to fly from Chicago to Winnipeg

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Winnipeg are during the month of February. You can find some of the cheapest flights from Chicago to Winnipeg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Winnipeg

Sunday is one of the best days to book for cheap flights from Chicago to Winnipeg: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Winnipeg

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Winnipeg in 2025. You can also book with separate airlines for your outbound and return journeys, from $139 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Winnipeg flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Winnipeg airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Winnipeg Flights

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*Available to One Key members.