Prices were found in the last 72 hours and may change — check the exact price when you continue.
On this page, you can find and book flights from Chicago to Winnipeg. The distance between the cities is 1,155 km, and there are approximately 9 weekly flights on this route.
Flights are operated by United Airlines and Air Canada. Since ticket prices are dynamic, we recommend using the price trend chart and calendar, as well as checking information on how to get to the airport in Chicago in advance.
Below is a calendar of the lowest flight ticket prices for Chicago — Winnipeg by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $170 in ,, and the most expensive are around $429 in a. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
Chicago → Winnipeg, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | $243 | low | May | $319 | high | Sep | $307 | medium |
| Feb | $256 | low | Jun | $345 | high | Oct | $256 | low |
| Mar | $281 | medium | Jul | $370 | high | Nov | $294 | medium |
| Apr | $294 | medium | Aug | $358 | high | Dec | $345 | high |
Some values are estimated based on seasonality.
The climate in Winnipeg is characterized by strong seasonality: July is the warmest month, with an average high temperature of 26.6°C. The lowest temperatures and significant cooling occur in January and February, when the thermometer can drop to -19°C.
August is considered the most budget-friendly period to fly, with ticket prices starting $170. Prices peak in May, when the minimum fare for the route increases to $429.
For an ideal balance between pleasant weather and cost, consider September, which offers moderate temperatures and tickets $171. Unless the trip is urgent, winter months should be avoided due to extreme frosts.
Two major airlines operate flights on the route from Chicago to Winnipeg: United Airlines and Air Canada. There are approximately 9 flights per week, the majority of which are direct, ensuring the shortest travel time. A detailed schedule, information on aircraft types, and specific departure days are available in the interactive list below.
Flights Chicago — Winnipeg depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Winnipeg James Armstrong Richardson International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
A direct flight on this 1,155 km route lasts an average of about 1 hour 40 minutes. Travel time may vary slightly depending on weather conditions and the chosen airline.
Regular flights between the cities are operated by major North American carriers — United Airlines and Air Canada.
Yes, direct flights are regularly available on this route, allowing you to reach your destination as quickly as possible without extra layovers.
Flights from the US arrive at Winnipeg James Armstrong Richardson International Airport (YWG). Information on how to get from the airport to the city center can be found in a dedicated section.
The cost depends on the season and booking time; current minimum prices for the coming months are always displayed in the calendar on this page.
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