Direct flights from Winnipeg to Chicago

Did you mean Flights from Chicago to Winnipeg?

Winnipeg

Canada

YWG

Winnipeg / James Armstrong Richardson International Airport

Chicago

United States

ORD

Chicago O'Hare International Airport

Route: Nonstop service available
Distance: 707 miles
Marketing airlines: 5 airlines
Aircraft: 2 aircraft types
Dates: Oct 19, 2026 – Oct 15, 2027

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Departure window: 2026-10-23 – 2026-11-21.

No recent fares appear in this limited preview. This does not mean the route is sold out. Use the search controls to check other dates and routes.

Winnipeg to Chicago route overview

Winnipeg / James Armstrong Richardson International Airport (YWG) serves Winnipeg; Chicago O'Hare International Airport (ORD) serves Chicago.

The airports are 707 miles apart by great-circle distance.

Roame's current schedule feed shows nonstop service from YWG to ORD.

Marketing airlines listed in the current schedule, including codeshare sellers, are Air Canada (AC), Avianca (AV), Copa Airlines (CM), Air New Zealand (NZ) and United Airlines (UA). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Oct 19, 2026 – Oct 15, 2027.

Marketing airlines on the Winnipeg to Chicago route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Air Canada (AC)Codeshare only
Avianca (AV)Codeshare only
Copa Airlines (CM)Codeshare only
Air New Zealand (NZ)Codeshare only

Airline alliance affiliations represented: Star Alliance

Aircraft flying from YWG to ORD

Frequently asked questions

Which airports serve the Winnipeg to Chicago route?

Winnipeg / James Armstrong Richardson International Airport (YWG) is the origin airport and Chicago O'Hare International Airport (ORD) is the destination airport.

How far is Chicago from Winnipeg?

YWG and ORD are approximately 707 miles apart by great-circle distance.

Are there direct flights from YWG to ORD?

Yes. Roame's current schedule feed shows nonstop service from YWG to ORD.

Which airlines market flights from YWG to ORD?

Which aircraft fly from YWG to ORD?

Aircraft listed in the current schedule include Embraer 175 (long wing) (E7W) and JET.