Flight prices from Chicago 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.

Which airports near Chicago or Winnipeg offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

• Airports in Chicago: 3 airports are active - Midway, O'Hare, Rockford.
• Airports in Winnipeg: Winnipeg is the only airport in use at the moment.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Explore flights from Chicago 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 Delta, United, American, and more.

Other popular destinations

Also interested in Canada? Check out: Calgary, Halifax, Montreal, 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.