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Cheap Flights from Chicago to Winnipeg
CHI → YWG • About 2h 20m nonstop • 2 airlines
Adults
+12 years old
Children
2-11 years old
Infants
Under 2 years
Fares shown are the lowest we have recorded recently on this route and are not a live quote. Run a search above for today's availability, or call (800) 399-8818 and an agent will price it with you.
Flights from Chicago (CHI) to Winnipeg (YWG)
The Chicago to Winnipeg route covers roughly 715 miles and takes about 2h 20m nonstop. 2 airlines compete on it — Air Canada, WestJet — which keeps fares moving and makes it worth comparing carriers rather than defaulting to the one you usually fly. We have seen one-way fares on this route start around $184.
Winnipeg sits at the geographic centre of North America and holds the Canadian Museum for Human Rights, one of the most striking museum buildings on the continent.
It is also the staging point for Churchill, the polar bear capital of the world, reachable by train or a further flight north.
Airlines flying CHI to YWG
- Air Canada
- WestJet
Airports on this route
- Departing: Chicago O'Hare International Airport (ORD)
- Departing: Chicago Midway International Airport (MDW)
- Arriving: Winnipeg Richardson International Airport (YWG)
Chicago is served by 2 airports. Fares between them can differ by $50 to $150 on the same dates, so ask us to price all of them before you book.
Best time to fly to Winnipeg
June through September. October and November are polar bear season in Churchill.
Top things to do in Winnipeg
- Canadian Museum for Human Rights
- The Forks
- Assiniboine Park Zoo
- Exchange District
- Churchill polar bear trips
- Manitoba Museum
- FortWhyte Alive
How to save on Chicago to Winnipeg flights
- Shift your departure by one or two days — midweek departures on this route are consistently cheaper than Friday and Sunday.
- Book four to eight weeks ahead. Last-minute fares on CHI to YWG routinely run double the advance price.
- Compare all 2 carriers rather than checking one airline's own site.
- Churchill has no road access — the train from Winnipeg takes two days, or fly.
- Polar bear season is October and November and books out a year ahead.
- Winnipeg winters are among the coldest of any major North American city.
About flights from Chicago to Winnipeg
Fares on the CHI to YWG route move with demand, so flexibility is worth more than timing tricks. Shifting your departure by a day or two, flying midweek instead of Friday or Sunday, and booking four to eight weeks ahead all reduce the fare on this route. Chicago is served by 2 airports, so ask us to price all of them — the difference is often significant. Our agents also hold consolidator and unpublished fares that do not appear in online results.
Air Canada, WestJet all operate on this route. Air Canada typically offers the most frequencies, with WestJet providing competing schedules. Availability varies by season and by which Chicago airport you depart from, so it is worth comparing all carriers before booking.
A nonstop flight takes about 2h 20m. Itineraries with a connection typically add two to four hours depending on the layover city and the length of the stop.
The two cities are roughly 715 miles apart by air.
Departures leave from Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Arrivals land at Winnipeg Richardson International Airport (YWG).
June through September. October and November are polar bear season in Churchill.