Winnipeg to Chicago (YWG–ORD) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
YWG–ORD is served by 2 airlines with nonstop service. United Airlines and JSX lead the route. The flight covers 707 miles in approximately 2h 34m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| UA United Airlines Also: AC, AV, CM | 42 | E75L, E7W | 2h06-2h34 | Star Alliance | AC, AV, CM | |
| XE JSX | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Travel Essentials
YWG: CDT · ORD: CDT
When it's 6:00 PM in Winnipeg, it's 6:00 PM in Chicago.
Canadian citizens do not need a visa or ESTA to enter the United States for tourism or business stays up to 6 months. A valid Canadian passport is required for air travel. Land and sea crossings also accept a NEXUS card, enhanced driver's license, or FAST card. At the border, officers determine the length of stay and may ask for proof of ties to Canada and a return plan.
CTA Blue Line runs 24/7 from O'Hare to downtown Chicago (45 min, $5). Taxis use a flat-rate zone system; downtown is around $40–45 plus tip. Ride-shares are typically $30–50.The Airport Transit System (ATS) connects all terminals and parking. Metra commuter rail does not serve O'Hare directly; transfer downtown via Blue Line.
Continental climate with four distinct seasons. Summers are warm and humid (25–32°C) with afternoon thunderstorms. Winters are cold (−10 to −2°C) with heavy snowfall that regularly delays flights December through March.
Spring and fall are mild but unpredictable. Pack layers. Lake Michigan moderates temperatures near the lakefront, but O'Hare sits inland and runs colder.
YWG–ORD Quick Facts
Frequently Asked Questions
Flights from YWG to ORD
Winnipeg / James Armstrong Richardson International Airport (YWG) and Chicago O'Hare International Airport (ORD) are connected by nonstop service from United Airlines and JSX. With 70 weekly departures, this is a heavily served route.
YWG to ORD Flight Duration and Schedule
Nonstop flight time from YWG to ORD is about 2 hours 34 minutes gate to gate. The route covers a distance of 707 miles (1,138 km). There are approximately 70 weekly flights outbound and 43 return, totaling 113 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Minneapolis–Saint Paul, Toronto Pearson and Denver. Two-stop connections are also available via intermediate hubs.