Flights from Winnipeg to Chicago, United States

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Did you mean flights from Chicago to Winnipeg?

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.

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

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

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $1,093 $839
7-14 days $951 $642
14-21 days $649 $608
21-30 days $640 $557
30-60 days $490 $412
60-90 days $490 $461
90+ days $490 $414

Compare Flight Prices from Winnipeg to Chicago 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 Winnipeg to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Winnipeg Chicago United 20-05-22 20-05-24 2 $1,015
June Winnipeg Chicago Major Airlines 20-06-06 20-06-15 2 $430
July Winnipeg Chicago Major Airlines 20-07-20 20-07-28 2 $461
August Winnipeg Chicago Major Airlines 20-08-20 20-08-23 2 $414
September Winnipeg Chicago Major Airlines 20-09-06 20-09-20 2 $422
October Winnipeg Chicago Major Airlines 20-10-26 20-11-03 2 $434
November Winnipeg Chicago Air Canada 20-11-03 20-11-11 0 $490
December Winnipeg Chicago United 20-12-24 21-01-06 1 $494

Cheap Last Minute Flights from Winnipeg to Chicago

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

Next 30 Days

SunMonTueWedThuFriSat
9 10 11 12 13 14 15
$921
16 17 18 19 20 21 22
$921 $790
23 24 25 26 27 28 29
$790 $483
1 2 3 4 5 6 7
$483 $483
8 9 10 11 12 13 14
$483 $474
15 16 17 18 19 20 21
$474

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 $520.

The average price for direct flights from Winnipeg to Chicago is $520.

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

Weekly Direct Flights from Winnipeg to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 2 2 2 2 3 2 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.

The average price for one way flights from Winnipeg to Chicago is $250.

The average price for round trip flights from Winnipeg to Chicago is $520.

Winnipeg to Chicago Flight Questions

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

Question: How long is the flight from Winnipeg to Chicago?
Answer: The average Winnipeg to Chicago flight time is 2 hours and 29 minutes.
Question: How far is Chicago from Winnipeg?
Answer: The distance from Winnipeg to Chicago is 1,136 kilometers (706 miles).
Question: How common are direct flights from Winnipeg to Chicago?
Answer: There are 13 direct flights from Winnipeg to Chicago.
Question: What are the most popular Winnipeg airlines for direct flights from Winnipeg to Chicago?
Answer: United Airlines provides 100% of the non-stop flights between Winnipeg and Chicago.

Airlines in Winnipeg flying to Chicago Last modified: Jun 6, 2020 5:10 -04:00Number of routes searched: 0Number of itineraries searched: 0

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

Winnipeg to Chicago Airports

These are the major commercial airports we're currently monitoring in Winnipeg and Chicago. 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 Domestic Flights from Winnipeg - YWG Last modified: Jun 6, 2020 5:10 -04:00

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Cheap Flights from Winnipeg to Chicago