Are there nonstop flights from Chicago (ORD) to Winnipeg (YWG)?

Yes. United Express fly this route. Flight time is about 1h 50m.

What is the fastest connection from Chicago (ORD) to Winnipeg (YWG)?

via Minneapolis ≈ 2h 23m, via Toronto ≈ 3h 35m, via Denver ≈ 4h 10m (estimated flying time, excluding layovers).

from 15,000 ANA miles (economy, one way, based on the published award charts).

Chicago O'Hare International Airport (ORD) to Winnipeg / James Armstrong Richardson International Airport (YWG)・1,138 km

Nonstop flights available (1 airline). Flight time about 1h 50m. Nonstop return flights also operate.

With milesANA 15,000 miles+ (via YYZ)Economy, one way, estimate. Tap a connection for miles by cabin.

4 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

Times are estimated from distance. Check schedules, frequency and availability with the airline or a booking site.