$135 Cheap Flights from Chicago (ORD) to Winnipeg (YWG)

View $135 flight on Fri, Dec 5, 2025Opens in a new window

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

  • 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 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Winnipeg (ORD-YWG)

Prices were available within the past 7 days and start at $135 for one-way flights and $326 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Sat, Oct 18 - Tue, Oct 21
ORD
Chicago
YWG
Winnipeg
$326 Roundtrip, found 6 days ago
$326
Roundtrip
found 6 days ago
Select WestJet flight, departing Sat, Oct 18 from Chicago to Winnipeg, returning Tue, Oct 21, priced at $326 found 6 days ago
Delta
Wed, Sep 10 - Sun, Sep 14
ORD
Chicago
YWG
Winnipeg
$335 Roundtrip, found 5 days ago
$335
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 10 from Chicago to Winnipeg, returning Sun, Sep 14, priced at $335 found 5 days ago
United
Fri, Oct 24 - Mon, Oct 27
ORD
Chicago
YWG
Winnipeg
$338 Roundtrip, found 5 days ago
$338
Roundtrip
found 5 days ago
Select United flight, departing Fri, Oct 24 from Chicago to Winnipeg, returning Mon, Oct 27, priced at $338 found 5 days ago
Air Canada
Fri, Oct 24 - Mon, Oct 27
ORD
Chicago
YWG
Winnipeg
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Oct 24 from Chicago to Winnipeg, returning Mon, Oct 27, priced at $343 found 5 days ago
Delta
Tue, Oct 14 - Sat, Oct 18
ORD
Chicago
YWG
Winnipeg
$348 Roundtrip, found 4 days ago
$348
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 14 from Chicago to Winnipeg, returning Sat, Oct 18, priced at $348 found 4 days ago
Air Canada
Fri, Oct 24 - Mon, Oct 27
ORD
Chicago
YWG
Winnipeg
$350 Roundtrip, found 5 days ago
$350
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Oct 24 from Chicago to Winnipeg, returning Mon, Oct 27, priced at $350 found 5 days ago
Delta
Tue, Oct 14 - Sat, Oct 18
ORD
Chicago
YWG
Winnipeg
$357 Roundtrip, found 4 days ago
$357
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 14 from Chicago to Winnipeg, returning Sat, Oct 18, priced at $357 found 4 days ago
United
Tue, Sep 2 - Fri, Sep 5
ORD
Chicago
YWG
Winnipeg
$360 Roundtrip, found 5 days ago
$360
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 2 from Chicago to Winnipeg, returning Fri, Sep 5, priced at $360 found 5 days ago
United
Thu, Aug 28 - Wed, Sep 3
ORD
Chicago
YWG
Winnipeg
$362 Roundtrip, found 4 days ago
$362
Roundtrip
found 4 days ago
Select United flight, departing Thu, Aug 28 from Chicago to Winnipeg, returning Wed, Sep 3, priced at $362 found 4 days ago
Air Canada
Tue, Sep 2 - Fri, Sep 5
ORD
Chicago
YWG
Winnipeg
$365 Roundtrip, found 5 days ago
$365
Roundtrip
found 5 days ago
Select Air Canada flight, departing Tue, Sep 2 from Chicago to Winnipeg, returning Fri, Sep 5, priced at $365 found 5 days ago

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

September is typically the cheapest month to fly

From $303 - $738 per traveler.

Graph displaying average flight prices per month

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 $429
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $429
Flights from Chicago (ORD) to Winnipeg (YWG)
Origin airport
O'Hare Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Air Canada, Delta, United, WestJet
Roundtrip price
$325
Distance
706 mi
Average flight time
2 hours 32 mins

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 October. 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 $135 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.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) cost?
Snag cheap return tickets starting at $407 from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United and Air Canada flight leaving ORD on August 1 2025 and touching down at YWG. The price was last updated on July 18 2025 and has not changed since.
What is the cheapest month to fly from ORD to YWG?
The cheapest flights from ORD to YWG are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 ORD to YWG?
With tickets starting at $183 for a one-way flight from ORD to YWG, United is currently the cheapest carrier flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on September 25 2025. Prices were last updated on July 18 2025 and have not changed since.
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.

Explore a world of travel with Expedia

*Available to One Key members.