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Cheap Flights from Winnipeg to Chicago, IL, United States - YWG to CHI

Popular flights from Winnipeg to Chicago

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
12-Jun-2016 16-Jun-2016 $495
American Airlines
Departure Date Return Date Lowest Price
1-Jun-2016 17-Jun-2016 $646
United Airlines
Departure Date Return Date Lowest Price
17-Jun-2016 19-Jun-2016 $516
WestJet
Departure Date Return Date Lowest Price
10-Aug-2016 17-Aug-2016 $518

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

We have collected flight cost data from across the web for travel from Winnipeg to Chicago, and have found the average flight price for this trip to be $524.

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

Airlines can adjust prices for plane 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 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 Winnipeg to Chicago

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

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $1,312 $574
7-14 days $782 $538
14-21 days $543 $551
21-30 days $540 $551
30-60 days $516 $495
60-90 days $540 $506
90+ days $496 $490

Cheapest Day To Fly from Winnipeg to Chicago

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

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$496 $538 $540 $543 $496 $558 $495

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

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 Winnipeg to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
15 16 17 18 19 20 21
$940
22 23 24 25 26 27 28
$940 $543
29 30 31 1 2 3 4
$543 $568
5 6 7 8 9 10 11
$568 $543
12 13 14 15 16 17 18
$543

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

Your Winnipeg to Chicago 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 Winnipeg to Chicago is $568.

The average price for non-stop flights from Winnipeg to Chicago is $538.

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

Nonstop Flight Details from Winnipeg to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 3 3 2 3 3 2 4 07:10 17:40

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

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.

The average price for one way flights from Winnipeg to Chicago is $305.

The average price for round trip flights from Winnipeg to Chicago is $567.

Winnipeg to Chicago Flight Questions

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

Question: How long is a direct flight from Winnipeg to Chicago?
Answer: The average Winnipeg to Chicago flight time is 2 hours and 19 minutes.
Question: How many kilometers are there between Winnipeg and Chicago?
Answer: The distance from Winnipeg to Chicago is 1136 kilometers.
Question: How common are direct flights from Winnipeg to Chicago?
Answer: There are 19 direct flights from Winnipeg to Chicago.
Question: What is the most popular airline for non-stop flights from Winnipeg to Chicago?
Answer: United Airlines provides 100% of the non-stop flights between Winnipeg and Chicago.
Question: What are the most popular connecting cities when flying from Winnipeg to Chicago?
Answer: Minneapolis - St Paul, MN

Airlines Flying from Winnipeg to Chicago (YWG to CHI)

Below are the different airlines that fly from Winnipeg to Chicago 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 Winnipeg to Chicago.

Winnipeg to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
Air Canada YUL X X X X X X X
Delta MSP X X X X X X X
Delta MSP / DTW 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 Winnipeg and Chicago, 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 Winnipeg - YWG

FlightsAirlineLowest Price
Winnipeg to Toronto Air Canada, Bearskin, Porter, WestJet $362
Winnipeg to Windsor Air Canada, Bearskin, Porter, WestJet $468
Winnipeg to London Air Canada, Bearskin, WestJet $380

Cheap International Flights from Winnipeg - YWG

FlightsAirlineLowest Price
Winnipeg to Milwaukee American, Air Canada, United, WestJet $429
Winnipeg to New York Canadian Nth, American, Air Canada, Alaska, JetBlue, Frontier, Bearskin, Spirit, Porter, United, Virgin America, WestJet, Great Lakes $378
Winnipeg to South Bend Air Canada, Allegiant, United, WestJet Check Dates
Winnipeg to Minneapolis - St Paul American, Air Canada, Spirit, United, WestJet $595
Winnipeg to Madison American, Air Canada, United, WestJet $456
Winnipeg to Detroit American, Air Canada, Bearskin, Spirit, United, WestJet $439
Winnipeg to Atlanta American, Air Canada, Alaska, Frontier, Bearskin, United, WestJet $392
Winnipeg to Indianapolis American, Air Canada, United, WestJet $446
Winnipeg to Peoria American, Air Canada, United, WestJet Check Dates
Winnipeg to Grand Rapids American, Air Canada, United, WestJet $433
Winnipeg to St Louis American, Air Canada, Alaska, Frontier, Bearskin, United, WestJet $454
Winnipeg to Lansing American, Air Canada, United, WestJet Check Dates
Winnipeg to Dallas - Ft Worth American, Air Canada, Alaska, Bearskin, Spirit, United, WestJet $352
Winnipeg to Las Vegas American, Air Canada, Alaska, JetBlue, Frontier, Bearskin, Spirit, United, Virgin America, WestJet $374
Winnipeg to Ft Wayne American, Air Canada, United, WestJet $786
Winnipeg to Orlando American, Air Canada, Alaska, JetBlue, Frontier, Allegiant, Bearskin, Air Transat, United, WestJet $398
Winnipeg to Nashville American, Air Canada, Alaska, Bearskin, United, WestJet $348
Cheap Flights from Winnipeg to Chicago, IL, United States, from $385 Round trip from YWG to CHI