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.

Are there multiple airports in Chicago and Winnipeg?

If your departure or arrival city has more than one airport, it's worth comparing all of them for timing and pricing.

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

If you're traveling with a group or bulky luggage, look into parking or transport options. Alternative airports may offer faster transfers or better rates.

Adjust your flight filters for Chicago O'Hare – Winnipeg

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to Canada? These cities are popular too: Calgary, Montreal, Quebec, Toronto, Vancouver.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.