Flights from Chicago to Winnipeg, Canada

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Did you mean flights from Winnipeg to Chicago?

Chicago to Winnipeg Last modified: Aug 22, 2019 3:16 -04:00

We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to Winnipeg. Major Airlines & United frequently offer the best deals to Winnipeg flights, or select your preferred carrier below to see the cheapest days to fly.

Major Airlines
CHIYWG
Thu 12/5
2 stops
YWGCHI
Sat 12/7
2 stops
$388
United
CHIYWG
Thu 11/7
nonstop
YWGCHI
Wed 11/20
nonstop
$472
Air Canada
CHIYWG
Thu 11/7
1 stop
YWGCHI
Wed 11/20
1 stop
$475
WestJet
CHIYWG
Wed 10/30
1 stop
YWGCHI
Sat 11/2
1 stop
$560

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 $422.

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.

How far in advance should I book tickets from Chicago to Winnipeg?

The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Winnipeg.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $823 $690
7-14 days $699 $529
14-21 days $474 $450
21-30 days $473 $425
30-60 days $473 $389
60-90 days $472 $397
90+ days $473 $388

Cheapest Day To Fly from Chicago to Winnipeg

We've examined 57,595,778,181 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 Wednesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$425$425$410$413$410$415$450

Compare Flight Prices from Chicago to Winnipeg by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Chicago to Winnipeg flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
August Chicago Winnipeg Major Airlines 8/30/19 9/4/19 1 $659
September Chicago Winnipeg Major Airlines 9/21/19 9/29/19 1 $415
October Chicago Winnipeg Major Airlines 10/30/19 11/2/19 1 $414
November Chicago Winnipeg Major Airlines 11/6/19 11/20/19 2 $410
December Chicago Winnipeg Major Airlines 12/5/19 12/7/19 2 $388
January Chicago Winnipeg United 1/16/20 1/23/20 0 $473
February Chicago Winnipeg Major Airlines 2/13/20 2/21/20 2 $367
March Chicago Winnipeg United 3/17/20 3/19/20 0 $474

Cheap Last Minute Flights from Chicago to Winnipeg

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Winnipeg. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
18 19 20 21 22 23 24
$908
25 26 27 28 29 30 31
$908 $771
1 2 3 4 5 6 7
$771 $529
8 9 10 11 12 13 14
$529 $474
15 16 17 18 19 20 21
$474 $474
22 23 24 25 26 27 28
$474

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 $454.

The average price for direct flights from Chicago to Winnipeg is $523.

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 3 3 3 3 3 2 3 02:53 14:35

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.

The average price for one way flights from Chicago to Winnipeg is $293.

The average price for round trip flights from Chicago to Winnipeg is $456.

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 24 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 20 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.
Question: What are the most popular connecting cities when flying from Chicago to Winnipeg?
Answer: Toronto, ON

Airlines in Chicago flying to Winnipeg Last modified: Aug 22, 2019 3:16 -04:00Number of routes searched: 65Number of itineraries searched: 110,567

Wondering which airlines fly out of Chicago to Winnipeg? We've gathered the average price of Chicago airlines with flights to Winnipeg. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Chicago to Winnipeg
Airline Connections Mon Tue Wed Thu Fri Sat Sun
Air Canada -
United -
Air Canada YOW
Air Canada YUL
Air Canada YVR
Air Canada YYC
Major Airlines MSP
United DEN

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 International Flights from Chicago - CHI Last modified: Aug 22, 2019 3:16 -04:00

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Cheap Flights from Chicago to Winnipeg