Trip to Chicago

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Flights found

Planes from Winnipeg to Chicago

🛫 Flying from Winnipeg to Chicago is a convenient option, with the quickest direct flight taking just 2 hours and 28 minutes. 💰 Depending on the airline and time of booking, the prices for flights between Chicago and Winnipeg can range from C$181 to C$1225, making it essential to plan ahead for the best deals.

Where to stay in Chicago

There are over 656 hotels to stay in Chicago. Prices range from $19 per night.

Accomodation
  • Air Canada, United Airlines, and Delta are the major airlines that offer flights from Winnipeg Airport to Chicago O'Hare Airport. These airlines provide several daily flights between the two cities, offering travelers a variety of options for their journey. It is advisable to check the airlines' websites or contact their customer service for the most up-to-date flight schedules and availability before booking your trip. Make sure to compare prices and check for any additional fees or restrictions when choosing your airline for this route.
  • The flight from Winnipeg to Chicago typically takes approximately 5 hours and 36 minutes. This duration may vary depending on factors such as the airline, weather conditions, and any layovers or connecting flights. It is important to check the specific flight itinerary provided by the airline when booking your trip to get an accurate estimate of the travel time. Additionally, be sure to factor in any time zone differences between the two cities when planning your journey.
  • The cost of a flight from Winnipeg to Chicago can vary depending on several factors such as the airline, time of booking, and travel dates. On average, prices for a round-trip ticket between the two cities range from C$184 to C$1245. It is recommended to compare prices across different airlines and booking platforms to find the best deals for your travel budget. Additionally, booking in advance or being flexible with your travel dates can help you secure lower fares for your trip.