How much should you expect to spend for a flight from Winnipeg to Chicago Midway?

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

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

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

Is there more than one airport in Winnipeg or Chicago?

Even short-haul routes can benefit from considering secondary airports. It may open up more flight times or cheaper fares.

• Airports in Winnipeg: Only Winnipeg is currently operational.
• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

Airports with more daily flights offer more flexibility if plans change or delays occur. If you’re flexible, consider airports near Chicago as well.

Customize your flight from Winnipeg to Chicago Midway

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 the best airlines and travel agencies.

Other popular destinations

Thinking about United States? You might also consider: Las Vegas, 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.