Flights Winnipeg to Chicago YWG to ORD

Flights from Winnipeg (YWG) to Chicago (ORD): 2 airlines operate 16 flight numbers on this route, about 5 flights a week, distance 1138 km / 707 miles. No departures are scheduled in the next 30 days; the latest flight was OO5639 on Fri, Nov 13, 2026.

Airlines and flight numbers count operating flights from a year ago to a year ahead; code-share numbers are not counted. On time means landed less than 15 minutes late.

YWG Winnipeg Winnipeg International Airport ORD Chicago Chicago O'Hare International Airport
Route map YWG to ORD Great-circle route from Winnipeg International Airport, Canada to Chicago O'Hare International Airport, United States, 1138 km. Map data: Natural Earth. YWG ORD Map data: Natural Earth

Winnipeg to Chicago Flights

16 flight numbers from YWG to ORD, with the date each last flew. Local times: YWG CDT, ORD CST.

Flight Airline Last seen Departure Arrival
OO5639 SkyWest Airlines Nov 13, 2026 15:15 16:50
UA5639 United Airlines Nov 11, 2026 15:15 16:50
OO6005 SkyWest Airlines Oct 24, 2026 07:00 09:35
UA6005 United Airlines Oct 24, 2026 07:00 09:35
OO5144 SkyWest Airlines Oct 13, 2026 11:10 13:10
OO5466 SkyWest Airlines Sep 23, 2026 14:00 16:35
OO5809 SkyWest Airlines Sep 23, 2026 07:00 09:35
UA5466 United Airlines Sep 22, 2026 14:00 16:35
UA5809 United Airlines Sep 19, 2026 07:00 09:35
OO5209 SkyWest Airlines Sep 10, 2026 11:00 13:06
OO5511 SkyWest Airlines Aug 10, 2026 12:56 15:30
OO5491 SkyWest Airlines Aug 10, 2026 07:00 09:34
UA5491 United Airlines Aug 6, 2026 07:00 09:34
UA5511 United Airlines Jul 30, 2026 12:56 15:30
UA5250 United Airlines Jun 24, 2026 12:56 15:30
UA5747 United Airlines Jun 24, 2026 07:00 09:34

Upcoming flights

Local times at the departure airport.

No upcoming flights for this route.

Recent flights

Local times at the departure airport.
Flight From To Date Scheduled Time Departure Status Details
OO5639 Winnipeg YWG Chicago ORD Nov 13 15:15 15:19 Landed Track >
OO5639 Winnipeg YWG Chicago ORD Nov 12 15:15 15:25 Landed Track >
UA5639 Winnipeg YWG Chicago ORD Nov 11 15:15 Scheduled Track >
OO5639 Winnipeg YWG Chicago ORD Nov 11 15:15 15:30 Landed Track >
OO5639 Winnipeg YWG Chicago ORD Nov 10 15:15 17:23 Delayed Track >
OO5639 Winnipeg YWG Chicago ORD Nov 09 15:15 15:29 Landed Track >
OO5639 Winnipeg YWG Chicago ORD Nov 08 15:15 15:17 Landed Track >
OO5639 Winnipeg YWG Chicago ORD Nov 07 15:15 15:25 Landed Track >
UA5639 Winnipeg YWG Chicago ORD Nov 07 15:15 Scheduled Track >
UA5639 Winnipeg YWG Chicago ORD Nov 06 15:15 Scheduled Track >
OO5639 Winnipeg YWG Chicago ORD Nov 06 15:15 15:15 Landed Track >
OO5639 Winnipeg YWG Chicago ORD Nov 05 15:15 15:19 Landed Track >
UA5639 Winnipeg YWG Chicago ORD Nov 05 15:15 Scheduled Track >
OO5639 Winnipeg YWG Chicago ORD Nov 04 15:15 15:32 Landed Track >
UA5639 Winnipeg YWG Chicago ORD Nov 04 15:15 Scheduled Track >

Airlines flying YWG to ORD

YWG to ORD FAQ

How long is the flight from Winnipeg to Chicago?
About 55 min: that is the median flight time of the last 9 flights that landed; the timetable allows 1 h 35 min.
Which airlines fly from Winnipeg to Chicago?
United Airlines and SkyWest Airlines have flights from Winnipeg (YWG) to Chicago (ORD) between a year ago and a year ahead. An airline listed may not fly the route every day.
How many flights a week go from Winnipeg to Chicago?
About 5 flights a week, counted over the two weeks before and after today. Only operating flights are counted, not code-share numbers.
Are flights from Winnipeg to Chicago on time?
9 of the last 9 flights that landed arrived less than 15 minutes after their scheduled time.
How far is Winnipeg from Chicago?
1138 km (707 miles) in a straight line between Winnipeg International Airport and Chicago O'Hare International Airport.

Chicago (ORD) to Winnipeg (YWG) flights >