How much is a flight from Winnipeg to Chicago?

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

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

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Winnipeg - Chicago route.

Flying from or to Winnipeg and Chicago? Here are your airport options

Knowing your full list of nearby airports can make flight planning easier, especially when routes vary.

• Airports in Winnipeg: Only Winnipeg is available for departures.
• Airports in Chicago: Arrivals into Chicago are possible from 3 airports - Midway, O'Hare, Rockford.

For families or those traveling with assistance, smaller airports can be easier to navigate. Cities served by multiple airports often allow for more flexible travel planning.

Find flights from Winnipeg to Chicago 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 Ryanair, British Airways, Easyjet, and booking sites like Expedia and eDreams.

Other popular destinations

Interested in United States? These cities are also in demand: Las Vegas, 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.