On this page, you can book flight tickets from Winnipeg to Chicago. The distance between the cities is 1155 km, and the flight frequency is approximately 10 flights per week.
Flights are operated by UA and AC. To find the best deals, use our price dynamics chart and low-price calendar, as ticket prices vary depending on the booking date.
The table shows direct flights Winnipeg → Chicago on the selected date. The flight takes approximately 2 h 34 min. Regular flights are operated by United Airlines and Air Canada. Departures from Winnipeg James Armstrong Richardson International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.
For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.
Below is a calendar of the lowest flight ticket prices for Winnipeg — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 547 in ,, and the most expensive are around AED 1,247 in J. 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.
The climate in Chicago is characterized by warm summers with peak temperatures reaching 26.5°C in July and cold winters when the thermometer drops to -5°C in January. The highest rainfall occurs in May, reaching 126 mm.
The lowest flight cost was recorded in August, starting AED 547. The most expensive month to travel is January, with ticket prices starting AED 1,247.
The optimal time for booking is considered to be August, combining affordable prices and comfortable weather. It is best to avoid trips in January due to high prices and low temperatures.
Regular air service between the cities is provided by two main airlines: United Airlines and Air Canada. Direct flights are available on this route, with a total of about 10 departures per week. To check the current schedule, travel times, and select specific flight dates, please review the list of carriers in the interactive table below.
Flights Winnipeg — Chicago depart from Winnipeg James Armstrong Richardson International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
The estimated travel time for a direct flight is about 1 hour and 40 minutes, considering the distance of 1155 km.
The main carriers operating flights between these cities are United Airlines (UA) and Air Canada (AC).
Yes, direct flights are available on this route, with a frequency of approximately 10 weekly departures.
Flights from Winnipeg arrive at Chicago's major airports; specific terminal information is available when selecting a specific flight.
It is recommended to book tickets in advance. The current lowest prices and best periods to travel are shown in the calendar on this page.
Where travelers fly most — pick a route and check prices
