Cheap flights Winnipeg — Chicago (YWG — CHI)

Good to know - Cheap tickets Winnipeg — Chicago

Cheapest flight found $177
Minimal flight time 2h 22m
Flight distance 1154 km
Most popular airline United Airlines

Airfare Winnipeg – Chicago by month

Here you can find out in what months how much a ticket Winnipeg – Chicago costs to buy cheap plane tickets.

Month One-way Round-trip
February 2025
November 2024
October 2024
September 2024
August 2024
July 2024

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Winnipeg — Chicago

Departure Arrival Flight days Flight Airlines Flight time Airports
07:00 09:31 mon, tue, wed, thu, sun UA5389 United Airlines 2h 31m Winnipeg James Armstrong Richardson International Airport — O'Hare International Airport Select dates
14:15 16:37 daily UA5639 United Airlines 2h 22m Winnipeg James Armstrong Richardson International Airport — O'Hare International Airport Select dates
14:20 16:48 daily UA5468 United Airlines 2h 28m Winnipeg James Armstrong Richardson International Airport — O'Hare International Airport Select dates
14:20 16:51 mon, tue, thu, fri, sun UA5639 United Airlines 2h 31m Winnipeg James Armstrong Richardson International Airport — O'Hare International Airport Select dates
All routes

Popular airlines flying Winnipeg — Chicago

Flight Winnipeg – Chicago is served by 13 airlines.  1 airlines operate direct flights.


Airlines with direct flights


Other airlines flying with transfers

Flights Winnipeg — Chicago

The selection of cheap flights Winnipeg — Chicago

Here you can find and purchase the cheapest flights Winnipeg — Chicago from $177 and Winnipeg — Chicago — Winnipeg from $150.

The price of the flight Winnipeg — Chicago (United States) — Winnipeg from $150 (round-trip).

The average price of the flight Winnipeg — Chicago (United States) — Winnipeg $539 (round-trip).

Low cost flights Winnipeg — Chicago (YWG — CHI)

The distance between Winnipeg and Chicago 717 miles (or 1154 kilometres).

The time difference between Winnipeg and Chicago is 0 h.

Minimal flight time from Winnipeg to Chicago 2h 22m.

LowCostClub always do a comparison of airfares Winnipeg — Chicago with several airlines (include United Airlines). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Winnipeg — Chicago. Last week, for instance, the cheapest round-trip prices stood at $150 while the cheapest one-way price that was available within the last week cost $177

Routes from nearby cities to Chicago

A flight from a neighbouring city can help you save money on plane tickets.

The most frequent flight to Chicago is from Regina. The cheapest airfare can be purchased with a flight from Minneapolis from $45. The nearest airports from Winnipeg with a flight to Chicago are in Appleton.

Popular International routes from Winnipeg

Popular routes from Chicago

If you are going to fly from Chicago, then study the popular flights. The most popular flights from Chicago:

Popular domestic routes from Winnipeg

FAQ about Winnipeg — Chicago

Yes, they do: UA5389, UA5639, UA5468

Yes, you can fly from Winnipeg to Chicago. Winnipeg has an airport (Winnipeg James Armstrong Richardson International Airport) for flights. United Airlines departs from Winnipeg on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Air Canada, Atlas Air, Cathay Pacific, Delta Connection, FedEx, Korean Air, National Airlines, NetJets, Porter, Porter Airlines Canada, Sun Country Airlines, UPS, WestJet.

A direct flight lasts an average of 2h 22m, during which time the aircraft covers a distance of 1154 km.

The price of flights Winnipeg — Chicago starts from $177.

Planes fly Winnipeg — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Winnipeg — Winnipeg James Armstrong Richardson International Airport. In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport.

The following flights fly between Winnipeg and Chicago: UA5389, UA5639, UA5468, UA5639

High season is considered to be and the cheapest month is . Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Winnipeg — Chicago flight deals.

Only one airline operates a direct flight Winnipeg — Chicago: United Airlines.

All the following airlines flights Winnipeg — Chicago: Air Canada, Atlas Air, Cathay Pacific, Delta Connection, FedEx, Korean Air, National Airlines, NetJets, Porter, Porter Airlines Canada, Sun Country Airlines, United Airlines, UPS, WestJet.

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