Direct (nonstop) flights from Winnipeg to Chicago
1 airline flys nonstop from Winnipeg International (YWG) to Chicago O Hare International (ORD). It's 706 miles (1,137 km), about 2h 34m in the air. Operated by United Airlines.
United Airlines
Route data last updated: May 29, 2026
Airlines with non-stop flights
UA
United Airlines
Alternative Routes
Other ways to fly from Winnipeg to Chicago with one stop · direct emits 131 kg CO₂ per passenger
Looking for the return flight?
ORD → YWG: Flights from Chicago to WinnipegOther direct flights from Winnipeg
Direct flights from Chicago (ORD)
Frequently Asked Questions
How long is the direct flight from Winnipeg to Chicago?
A nonstop flight from Winnipeg (YWG) to Chicago (ORD) takes approximately 2 hours and 34 minutes. The distance is 706 miles (1,137 km).
Which airlines fly nonstop from Winnipeg to Chicago?
Just United Airlines.
Is there a nonstop flight from Winnipeg to Chicago?
Yes. 1 airline: United Airlines.
How far is Winnipeg from Chicago?
The flight distance from Winnipeg to Chicago is 706 miles (1,137 km), measured as the great-circle (shortest air) distance. That's roughly the same distance as the length of Italy.
What type of aircraft flies from Winnipeg to Chicago?
At 2h 34m, this route typically uses narrow-body or mid-range jets — Boeing 737 MAX or Airbus A320neo. Varies by airline.
Do I need a visa to travel from Canada to USA?
Depends on your passport. Check with the USA embassy or an official visa portal before booking — requirements change.
What is the carbon footprint of a flight from Winnipeg to Chicago?
Roughly 131 kg CO2 per passenger one-way. That's about the same as driving 655 km.
Is the return flight from Chicago to Winnipeg also nonstop?
Yes — nonstop flights run both ways. Flight time may differ slightly due to wind patterns.
When is the cheapest time to fly from Winnipeg to Chicago?
Midweek flights (Tue/Wed) outside holiday peaks are usually cheapest. 3-6 weeks ahead is a good window for this route. Use "Check Prices" above to compare.
How early should I arrive at Winnipeg International for this flight?
3 hours before departure for international flights. You need time for check-in, security, and immigration.