Flights from Chicago to Winnipeg, Canada

Did you mean flights from Winnipeg to Chicago?

Chicago to Winnipeg Last modified: Mar 26, 2024 19:37 -04:00

We've scanned 117,220,093 round trip itineraries and found the cheapest flights to Winnipeg. Multiple Airlines & Major Airlines frequently offer the best deals to Winnipeg flights, or select your preferred carrier below to see the cheapest days to fly.

Multiple Airlines
CHIYWG
Sat 5/25
nonstop
YWGCHI
Wed 5/29
nonstop
$389
Select
Major Airlines
CHIYWG
Wed 4/24
1 stop
YWGCHI
Sun 4/28
1 stop
$396
Select
United
CHIYWG
Sat 5/25
1 stop
YWGCHI
Wed 5/29
1 stop
$400
Select
Air Canada
CHIYWG
Sat 5/25
1 stop
YWGCHI
Wed 5/29
1 stop
$434
Select
WestJet
CHIYWG
Wed 4/24
1 stop
YWGCHI
Mon 4/29
1 stop
$476
Select
Multiple Airlines
CHIYWG
Wed 4/24
1 stop
YWGCHI
Sun 4/28
1 stop
$521
Select

How Much is a Flight from Chicago to Winnipeg?

We have collected flight cost data from across the web for travel from Chicago to Winnipeg, and have found the average flight price for this trip to be $395.

Where To Buy Cheap Flights from Chicago to Winnipeg?

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 Chicago to Winnipeg 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.

Cheapest Day To Fly from Chicago to Winnipeg

We've examined 234,440,186 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Winnipeg is Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$402$333$426$339$446 $422

Connecting Flights vs Direct Flights from Chicago to Winnipeg

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 Chicago to Winnipeg is not available.

The average price for direct flights from Chicago to Winnipeg is not available.

The chart below shows up to date information regarding non-stop flights from Chicago to Winnipeg.

Weekly Direct Flights from Chicago to Winnipeg - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 2 2 2 2 2 2 2 02:54 08:28

One Way Flights vs Round Trip Flights from Chicago to Winnipeg

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 Chicago to Winnipeg. 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

Chicago to Winnipeg Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from Chicago to Winnipeg?
Answer: The average Chicago to Winnipeg flight time is 2 hours and 35 minutes.
Question: How far is Winnipeg from Chicago?
Answer: The distance from Chicago to Winnipeg is 706 miles (1,136 kilometers).
Question: How common are direct flights from Chicago to Winnipeg?
Answer: There are 14 direct flights from Chicago to Winnipeg.
Question: What are the most popular Chicago airlines for direct flights from Chicago to Winnipeg?
Answer: United Airlines provides 100% of the non-stop flights between Chicago and Winnipeg.

Chicago to Winnipeg Airports

These are the major commercial airports we're currently monitoring in Chicago and Winnipeg. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

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.

Cheap Flights from Chicago to Winnipeg