Find out what a flight from Winnipeg to Chicago might cost

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

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

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.

Refine your flight search from Winnipeg to Chicago

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from the best airlines and travel agencies.

Other popular destinations

Also looking at United States? These cities are trending: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.