How much is a flight from Chicago Midway to Winnipeg?

There’s no fixed price — fares between Chicago and Winnipeg can vary a lot by day or time.

Pick a travel date to see today’s available fares.

Flying during the week can be more affordable, as weekend flights tend to be pricier. Also consider demand and availability: the last remaining seats often come at higher fares!

Which airports are most convenient between Chicago and Winnipeg?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Chicago: There are 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Winnipeg: Winnipeg is the only functioning airport for now.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

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 like Delta, United, American, and more.

Other popular destinations

Planning a trip to Canada? Other frequent searches include: Calgary, Edmonton, Montreal, 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.