Find out what a flight from Chicago Rockford to Winnipeg might cost

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

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.

Flying between Chicago and Winnipeg? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
• Airports in Winnipeg: The only active option is Winnipeg.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Chicago airports in a single search.

Match your flight search to your preferences: Chicago Rockford – Winnipeg

Jetcost makes it easy to find the right flight. Set filters for flight time, price, number of stops, and preferred airline. You’ll see offers from Expedia, Delta, United, American, and more.

Other popular destinations

Thinking about traveling to Canada? Other users also viewed: Calgary, Montreal, Quebec, Toronto, Vancouver.

Don’t forget to check change or cancellation policies, especially if your plans aren’t final. For a more targeted search, you can also set price limits directly in the filters.