Cheap flights from Winnipeg to Chicago O'Hare

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

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

Select your dates to check current offers.

Flying at off-peak hours — such as early morning or late evening — can help you save. Also, the best deals tend to appear in the weeks leading up to departure.

Flying between Winnipeg and Chicago? 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 Winnipeg: Winnipeg has only one airport in service, Winnipeg.
  • Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

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

Flights from Winnipeg to Chicago - O'Hare

Customize your flight from Winnipeg to Chicago O'Hare

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.
Frequently Asked Questions

Frequently asked questions about flights from Winnipeg to Chicago O'Hare.

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

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

How far is Winnipeg from Chicago?

Winnipeg is about 1138 km from Chicago.

What are the airports in Chicago?

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

What are the airports in Winnipeg?

Winnipeg has one airport: Winnipeg.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Winnipeg to Chicago?

The best time to book a flight from Winnipeg to Chicago is 1 month in advance, while the worst time is 3 weeks in advance.

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

This information is not available at the moment.

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

This information is not available at the moment.

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

This information is not available at the moment.