Cheap Flights from Chicago to Winnipeg
Cheap Flights from Chicago to Winnipeg
Looking for cheap flights from Chicago to Winnipeg? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Winnipeg vary by season, cabin, and date. There is no award space in the next two months right now. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Winnipeg for specific travel dates.
Chicago to Winnipeg flight facts
Distance
710 mi
1,143 km in a straight line
Estimated flight time
about 2h
In the air, for the straight-line distance
Time difference
+1h
Winnipeg is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Winnipeg
YWG · Winnipeg / James Armstrong Richardson Intl
Premium cabin flights from Chicago to Winnipeg
Selected hotels for your next stay
Frequently Asked Questions
The cheapest route from Chicago to Winnipeg depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Winnipeg.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Winnipeg.
Chicago and Winnipeg are about 710 miles (1,143 km) apart in a straight line.
Flying the 710-mile straight-line distance takes about 2h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Winnipeg is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Winnipeg: Winnipeg / James Armstrong Richardson Intl (YWG).
Travelers searching this route also look at other popular routes into Winnipeg, plus the return trip when we track it. Fares and award space change daily.
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Our mission is to provide the simplest and best
points travel planning experience. Yeah!
