Flight prices from Chicago Midway 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 departure and arrival airports are available?

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

• Airports in Chicago: Chicago is connected by 3 airports - Midway, O'Hare, Rockford.
• Airports in Winnipeg: Winnipeg is the only active airport in the area.

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

Plan your perfect flight from Chicago Midway to Winnipeg

Jetcost gives you full control over your flight search. Filter by date, time, duration, price, and airline. See round-trip and one-way options from low-cost and full-service carriers and more.

Other popular destinations

Planning a trip to Canada? Other frequent searches include: Calgary, Montreal, Quebec, Toronto, Vancouver.

Some airlines include baggage in the fare, others don’t — always check the details before booking. If you're looking for round-trip flights, you can easily see the most convenient combinations.