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Flights from Winnipeg to Chicago, United States
Winnipeg to Chicago Last modified: Mar 26, 2024 18:22 -04:00
We've scanned 117,220,093 round trip itineraries and found the cheapest flights to Chicago. Multiple Airlines & United frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.
Where To Buy Cheap Flights from Winnipeg to Chicago?
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Winnipeg to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.
Connecting Flights vs Direct Flights from Winnipeg to Chicago
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Winnipeg to Chicago is not available.
The average price for direct flights from Winnipeg to Chicago is not available.
The chart below shows up to date information regarding non-stop flights from Winnipeg to Chicago.
| Carrier | Mon | Tue | Wed | Thu | Fri | Sat | Sun | Earliest Flight | Latest Flight |
| United | 2 | 2 | 2 | 2 | 2 | 1 | 2 | 05:51 | 09:31 |
One Way Flights vs Round Trip Flights from Winnipeg to Chicago
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Winnipeg to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison. Find Flights
Winnipeg to Chicago Flight Questions
Below are some common questions that asked about this flight route:
Farecompare Research Tools
FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.
