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Cheap Flights from Chicago to Winnipeg, MB, Canada - CHI to YWG

Popular flights from Chicago to Winnipeg

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

Air Canada
Departure Date Return Date Lowest Price
Jun 5, 2016 Jun 13, 2016 $454
American Airlines
Departure Date Return Date Lowest Price
May 10, 2016 May 18, 2016 $470
United Airlines
Departure Date Return Date Lowest Price
Jun 2, 2016 Jun 6, 2016 $480
WestJet
Departure Date Return Date Lowest Price
May 26, 2016 May 31, 2016 $498

How Much Does it Cost to Fly from Chicago to Winnipeg (CHI to YWG)?

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 $483.

When Can I Buy the Cheapest Flight from Chicago to Winnipeg (CHI to YWG)?

Airlines can adjust prices for plane 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 discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Chicago to Winnipeg

The chart below shows up-to-date information regarding how far in advance a flight from Chicago to Winnipeg should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $0 $1,245
7-14 days $816 $518
14-21 days $724 $512
21-30 days $486 $480
30-60 days $486 $480
60-90 days $493 $507
90+ days $488 $475

Cheapest Day To Fly from Chicago to Winnipeg

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Winnipeg.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$491 $470 $508 $480 $467 $514 $454

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Winnipeg

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Winnipeg.

Next 30 Days

SunMonTueWedThuFriSat
8 9 10 11 12 13 14
$816
15 16 17 18 19 20 21
$816 $724
22 23 24 25 26 27 28
$724 $754
29 30 31 1 2 3 4
$754 $486
5 6 7 8 9 10 11
$486

Non-Stop vs Connecting Flights from Chicago to Winnipeg (CHI to YWG)

Your Chicago to Winnipeg flight can be significantly cheaper by choosing 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 $528.

The average price for non-stop flights from Chicago to Winnipeg is $508.

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

Nonstop Flight Details from Chicago to Winnipeg
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 3 3 2 3 3 3 4 08:55 19:37

Round Trip vs One Way Flights from Chicago to Winnipeg (CHI to YWG)

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 $267.

The average price for round trip flights from Chicago to Winnipeg is $526.

Chicago to Winnipeg Flight Questions

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

Question: How long is a direct flight from Chicago to Winnipeg?
Answer: The average Chicago to Winnipeg flight time is 2 hours and 18 minutes.
Question: How many miles are there between Chicago and Winnipeg?
Answer: The distance from Chicago to Winnipeg is 706 miles.
Question: How common are direct flights from Chicago to Winnipeg?
Answer: There are 19 direct flights from Chicago to Winnipeg.
Question: What is the most popular airline for non-stop 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: Detroit, MI and Minneapolis - St Paul, MN

Airlines Flying from Chicago to Winnipeg (CHI to YWG)

Below are the different airlines that fly from Chicago to Winnipeg with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Winnipeg.

Chicago to Winnipeg
Airline Connections Mon Tue Wed Thu Fri Sat Sun
Air Canada YYZ X X X X X X X
Delta MSP X X X X X X X
Delta DTW / MSP X X X X X X X
United - X X X X X X X
United DEN X X X X X X X
WestJet YYC X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Winnipeg, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to New York American, Alaska, JetBlue, Spirit, United $94
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $97
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $81
Chicago to Minneapolis - St Paul American, Frontier, Spirit, United $48
Chicago to Denver American, Alaska, Frontier, Spirit, United $81
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $79
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $132
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $186
Chicago to Seattle American, Alaska, Frontier, Spirit, United, Virgin America $197
Chicago to Phoenix American, Alaska, Frontier, Spirit, United $177
Chicago to Atlanta American, Spirit, United $71
Chicago to Washington American, Alaska, Frontier, United $118
Chicago to Houston American, Spirit, United $117
Chicago to Boston American, JetBlue, Spirit, United $79
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to Detroit American, United $175
Chicago to Fargo American, United $339

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet, Great Lakes $223
Chicago to London American, Air Berlin, Air France, Alaska, Finnair, Alitalia, JetBlue, British Airways, BMI, Condor, Aer Lingus, Iberia, Meridiana, KLM, Lufthansa, LOT, Thomas Cook, Czech, Arkefly, Austrian, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic $914

Cheap International Flights to Winnipeg - YWG

FlightsAirlineLowest Price
Indianapolis to Winnipeg American, Air Canada, United, WestJet $428
Milwaukee to Winnipeg American, Air Canada, United, WestJet $382
Madison to Winnipeg American, United, WestJet $390
Grand Rapids to Winnipeg American, Air Canada, United, WestJet $465
Peoria to Winnipeg American, Air Canada, United Check Dates
Lansing to Winnipeg United $411
South Bend to Winnipeg United Check Dates
Appleton to Winnipeg United Check Dates
Moline to Winnipeg Air Canada, Allegiant, United Check Dates
Green Bay to Winnipeg American, Air Canada, United, WestJet $390
Ft Wayne to Winnipeg American, Air Canada, United Check Dates
Cheap Flights from Chicago to Winnipeg, MB, Canada, from $454 Round trip from CHI to YWG