Cheap flights from Winnipeg to Chicago O'Hare International

Compare Winnipeg to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

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Flight deals from Winnipeg to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from Winnipeg to Chicago O'Hare International? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Winnipeg to Chicago O'Hare International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Winnipeg to Chicago O'Hare International flights are currently cheapest in May.

Direct flights from Winnipeg to Chicago O'Hare International

Winnipeg to Chicago O'Hare International: Alternative routes

Compare routes from Winnipeg to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Winnipeg to Chicago: Flight information

The things to know before you go.
Cheapest flight found$193
Cheapest month to flyMay
Average flight time2 hrs, 29 mins
Most popular airlineAir New Zealand
Average flights per week52

Finding cheap flights from Winnipeg to Chicago O'Hare International: Frequently asked questions

The best price we found for a return flight from Winnipeg to Chicago O'Hare International is $325. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 29 minutes is the average flight time from Winnipeg to Chicago O'Hare International.
Air New Zealand, Air Canada and United fly direct from Winnipeg to Chicago O'Hare International.
As of February 2026, there are 52 flights per week flying from Winnipeg to Chicago O'Hare International.
The cheapest month to fly from Winnipeg to Chicago O'Hare International is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Winnipeg Airport to Chicago O'Hare International Airport on Monday, 18 May 2026.
Yes – the average flight time is 2 hours and 29 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago O'Hare International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, WestJet and United offer the cheapest flight tickets to Chicago O'Hare International.

Travelling from Winnipeg James Armstrong Richardson International Airport (YWG) to O'Hare International Airport (ORD): what you need to know

  • Take a direct flight from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport and you'll be in the air for an average of 2 hours 30 minutes.

  • Chicago's timezone is UTC-5, which is the same as Winnipeg.

  • Take your pick of ten weekly Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport flights. The 14:15 departure with United Airlines is the earliest flight available. United Airlines operates the latest service of the day at 14:25.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to catch your YWG to ORD flight.

  • Travelling during a peak time such as July? Major public holidays and other high seasons can lead to longer queues at security. Play things extra safe and arrive up to four hours before international flights and two hours before a domestic departure.

  • Jetting into Chicago (and then discovering more of United States!) is a cinch with United Airlines. This popular airline has direct flights from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport.

  • The airline that passengers book most often on this route is United Airlines.

  • With 70.49% of its services landing as planned, United Airlines is the most punctual carrier operating YWG to ORD flights.

How to find the cheapest flights from Winnipeg James Armstrong Richardson International Airport (YWG) to O'Hare International Airport (ORD)

  • Currently, $193 is the lowest price we've seen for a one-way Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport flight. The best price for a return plane ticket is $325. Keep in mind that fares may change due to availability at the time of booking.

  • Get cheap tickets from YWG to ORD by booking at least seven months ahead. According to our research, that's the sweet spot for finding the biggest deals.

  • June is the cheapest month for flights from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport. If you need to travel during a different time of year, the 'Whole month' tool will show you the lowest airfares for each month.

  • Never miss a deal on cheap flights from YWG to ORD by setting up a Price Alert. We'll send you an email or notification on the app when a special offer becomes available.

  • Tailor your flights with filters. Pick your ideal arrival and departure times, airlines and total journey duration. You can also sort results by 'Best,' 'Fastest' or 'Cheapest' flights from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport.

Handy information about Winnipeg James Armstrong Richardson International Airport (YWG)

  • The address for YWG is 2000 Wellington Avenue.

  • Of the departures from Winnipeg James Armstrong Richardson International Airport, 61.28% arrive on time at their destination.

  • Central Winnipeg to Winnipeg James Armstrong Richardson International Airport is approximately 8 kilometres. Depending on traffic, it'll take you about 15 minutes to get there if you're ride-sharing, catching a cab or driving.

  • Planning to catch public transport? Expect a journey time of around 55 minutes.

  • Get your journey off to a stress-free start by staying near YWG. Whether you're taking an early flight from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport or want to avoid feeling rushed, these hotels are perfect:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

  • The address for ORD is 10000 West O'Hare.

  • From O'Hare International Airport, Chicago is approximately 40 kilometres away. It takes around 35 minutes to get to the centre driving.

  • Getting there by public transport typically takes 55 minutes.

When to fly to O'Hare International Airport (ORD)

  • It's time to pick your travel dates for your flight from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport. August is the busiest month to visit Chicago. If you'd like a more low-key vibe, go in January.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your flights from Winnipeg James Armstrong Richardson International Airport to O'Hare International Airport in this month if you like this kind of weather.

  • Look for cheap tickets from YWG to ORD in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored after you've experienced Chicago. Around 451 kilometres away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. No visit is complete without checking out The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.