Flight prices from Chicago O'Hare to Winnipeg

There’s no fixed price — fares between Chicago and Winnipeg can vary a lot by day or time.

Choose a date to explore the best fares now.

The lowest fares are often found with some flexibility in travel dates. If your plans are flexible, you’ll have a better chance of finding cheap flights.

Planning flights between Chicago and Winnipeg? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Chicago: 3 airports are listed in Chicago - Midway, O'Hare, Rockford.
• Airports in Winnipeg: Only Winnipeg is currently available.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

Explore flights from Chicago O'Hare to Winnipeg your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Ryanair, British Airways, Easyjet, and more.

Other popular destinations

Also interested in Canada? Check out: Calgary, Montreal, Quebec, Toronto, Vancouver.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.