Find out what a flight from Chicago Midway to Winnipeg might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Winnipeg.

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Flights between Chicago and Winnipeg: which airports can you choose?

The distance between Chicago and Winnipeg is about 1163 km. Checking alternative airports can help lower the total cost of your trip.

• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
• Airports in Winnipeg: Currently, the only available airport in Winnipeg is Winnipeg.

Choosing airports with fast connections to the city center can cut down total travel time. You can compare all flights from Chicago airports to find the best option.

Refine your flight search from Chicago Midway to Winnipeg

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from Expedia, eDreams, and top carriers.

Other popular destinations

Also looking at Canada? These cities are trending: Calgary, Montreal, Quebec, Toronto, Vancouver.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.