How much is a ticket from Winnipeg to Chicago?

Flight prices from Winnipeg to Chicago change depending on demand and time of booking.

Select your dates to check current offers.

Flying at off-peak hours — such as early morning or late evening — can help you save. Also, the best deals tend to appear in the weeks leading up to departure.

Which airports serve Winnipeg and Chicago?

When planning a trip of about 721 mi, it's a good idea to check flights from surrounding airports too.

• Airports in Winnipeg: Winnipeg is the only operational airport in the area.
• Airports in Chicago: Chicago offers flights from 3 airports - Midway, O'Hare, Rockford.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

Customize your flight from Winnipeg to Chicago

Jetcost allows you to filter by travel dates, duration, layovers, carriers, and booking providers. You’ll find direct and connecting flights, one-way or round-trip, from Delta, American, United, Expedia, eDreams, and more.

Other popular destinations

Thinking about United States? You might also consider: Boston, Los Angeles, Miami, New York City, Orlando.

You can sort results by price, duration, or departure time to find the best option for you. When available, results always include both low-cost and traditional airlines.