How much is a flight from Winnipeg to Chicago Midway?

Depending on when you travel and how far in advance you book, fares between Winnipeg and Chicago can differ a lot.

Select your dates to check current offers.

Low-cost airlines offer competitive fares, but often add charges for extra services. Keep that in mind when planning your trip. Also, midweek departures may offer better deals than weekends.

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.

Plan your perfect flight from Winnipeg to Chicago Midway

Jetcost gives you full control over your flight search. Filter by date, time, duration, price, and airline. See round-trip and one-way options from low-cost and full-service carriers and more.

Other popular destinations

Planning a trip to United States? Other frequent searches include: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Some airlines include baggage in the fare, others don’t — always check the details before booking. If you're looking for round-trip flights, you can easily see the most convenient combinations.