How much is a flight from Winnipeg to Chicago O'Hare?

There’s no fixed price — fares between Winnipeg and Chicago 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!

Are there multiple airports in Winnipeg and Chicago?

If your departure or arrival city has more than one airport, it's worth comparing all of them for timing and pricing.

• Airports in Winnipeg: Only Winnipeg operates in this city.
• Airports in Chicago: 3 airports are available in Chicago - Midway, O'Hare, Rockford.

If you're traveling with a group or bulky luggage, look into parking or transport options. Alternative airports may offer faster transfers or better rates.

Plan smarter: flights from Winnipeg to Chicago O'Hare

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to United States also checked out: Atlanta, Los Angeles, Miami, New York City, Orlando.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.