Flight prices from Winnipeg to Chicago O'Hare

There’s no fixed price — fares between Winnipeg and Chicago 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 departure and arrival airports are available?

Between Winnipeg and Chicago, flight options may depend on the combination of airports available.

• Airports in Winnipeg: Only Winnipeg is currently in operation.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Find flights from Winnipeg to Chicago O'Hare that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from the best airlines and travel agencies.

Other popular destinations

Interested in United States? These cities are also in demand: Atlanta, Los Angeles, Miami, New York City, Orlando.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.