Good to know - Cheap tickets Winnipeg — Chicago
| Minimal flight time | 2h 25m |
|---|---|
| Flight distance | 1154 km |
| Most popular airline | United Express |
| Round-trip from | $120 |
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 |
|---|---|---|
| September 2026 | ||
| August 2026 | ||
| June 2026 | ||
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| January 2026 | ||
| December 2025 | ||
| October 2025 | ||
| September 2025 |
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 | |
|---|---|---|---|---|---|---|---|
| 14:20 | 16:45 | daily | UA5639 | United Express | 2h 25m | Winnipeg James Armstrong Richardson International Airport — O'Hare International Airport | Select dates |
Popular airlines flying Winnipeg — Chicago
Flight Winnipeg – Chicago is served by 11 airlines. 1 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Dynamics airfare Winnipeg — Chicago by month for the last year
according to LowCost.Club for the last year
The airfare depends on the departure date. Our chart shows the low season prices on route Winnipeg — Chicago
The graph shows that booking flights Winnipeg — Chicago is best planned for January and flights Winnipeg — Chicago — Winnipeg in the month of September.
Flights Winnipeg — Chicago
The selection of cheap flights Winnipeg — Chicago
The price of the flight Winnipeg — Chicago (United States) — Winnipeg from $120 (round-trip).
The average price of the flight Winnipeg — Chicago (United States) — Winnipeg $240 (round-trip).
- Departure city: Winnipeg
- IATA code of the city of origin: YWG
- Departure airports: Winnipeg James Armstrong Richardson International Airport
- Departure country: Canada
- Destination city: Chicago
- IATA code of the destination city: CHI
- Destination airports: Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport
- Destination country: United States
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 25m.
Routes from nearby cities to Chicago
A flight from a neighbouring city can help you save money on plane tickets.
The closest airports to Winnipeg with a flight to Chicago are in Minneapolis.
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
Are there any direct flights Winnipeg — Chicago?
Yes, they do: UA5639
Can we fly from Winnipeg to Chicago?
Yes, you can fly from Winnipeg to Chicago. Winnipeg has an airport (Winnipeg James Armstrong Richardson International Airport) for flights. United Express departs from Winnipeg on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Air Canada, Atlas Air, British Airways, Delta Connection, FedEx, NetJets, Nippon Cargo Airlines, Porter, Porter Airlines Canada, UPS, WestJet.
How long does it take to fly from Winnipeg to Chicago?
A direct flight lasts an average of 2h 25m, during which time the aircraft covers a distance of 1154 km.
How much do flights Winnipeg — Chicago cost?
The price of flights Winnipeg — Chicago starts from $120.
What days does the plane fly Winnipeg — Chicago?
Planes fly Winnipeg — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Winnipeg and Chicago?
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.
What flights are currently flying from Winnipeg to Chicago?
The following flights fly between Winnipeg and Chicago: UA5639
What month is the cheapest to fly from Winnipeg to Chicago?
High season is considered to be December and the cheapest month is January. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Winnipeg — Chicago flight deals.
Which airlines direct fly from Winnipeg to Chicago?
Only one airline operates a direct flight Winnipeg — Chicago: United Express.
Which airlines fly from Winnipeg to Chicago?
All the following airlines flights Winnipeg — Chicago: Air Canada, Atlas Air, British Airways, Delta Connection, FedEx, NetJets, Nippon Cargo Airlines, Porter, Porter Airlines Canada, United Express, UPS, WestJet.