Cheap flights from Chicago to Winnipeg

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How much is a flight from Chicago to Winnipeg?

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

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 Chicago - Winnipeg route.

Flights between Chicago and Winnipeg: which airports can you choose?

The distance between Chicago and Winnipeg is about 721 mi. Checking alternative airports can help lower the total cost of your trip.

  • Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
  • Airports in Winnipeg: Currently, the only available airport in Winnipeg is Winnipeg.

Choosing airports with fast connections to the city center can cut down total travel time. You can compare all flights from Chicago airports to find the best option.

Flights from Chicago to Winnipeg

Explore flights from Chicago to Winnipeg your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Ryanair, British Airways, Easyjet, and more.

Other popular destinations

Also interested in Canada? Check out: Calgary, Montreal, Quebec, Toronto, Vancouver.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to Winnipeg.

How much does an airline ticket from Chicago to Winnipeg cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to Winnipeg.

How far is Chicago from Winnipeg?

Chicago is about 721 mi from Winnipeg.

What are the airports in Winnipeg?

Winnipeg has one airport: Winnipeg.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Canada?

The most popular cities in Canada according to our users' searches are: Calgary, Montreal, Quebec, Toronto, Vancouver.

When should I book a flight from Chicago to Winnipeg?

This information is not available at the moment.

What is the cheapest month to fly from Chicago to Winnipeg?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Winnipeg?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Winnipeg?

This information is not available at the moment.