Airlines with flights from Winnipeg to Chicago
There are two airlines with scheduled flights between YWG and ORD. United is the only airline with non-stop flights from Winnipeg International to Chicago O'Hare and the flight time is 2 hours and 34 minutes. You can also connect with Delta via Minneapolis with a flight time of 3 hours and 39 minutes.
Choose airline
Schedules
Non-stop with United Airlines
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Total flight time: 2 hours and 34 minutes
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Chicago is a United Airlines hub (Largest hub ).
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14 flights per week
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Embraer 175 (Enhanced Winglets)
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First class available
YWG
Direct
ORD
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
UA5747
07:00
07:00
07:00
07:00
07:00
07:00
07:00
UA5250
12:56
12:56
12:56
12:56
12:56
12:56
12:56
The timetable & schedule information was updated at 2026-04-22
Via Minneapolis with Delta Air Lines
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Total flight time: 3h 39m - 7h 58m.
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Sky Team Alliance
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74 flights per week
YWG
Via MSP
ORD
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL3660
DL1567
DL1567
06:40
06:40
06:40
06:40
06:40
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06:40
DL3660
DL4767
DL4767
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----
----
----
----
06:40
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DL3871
DL1306
DL1306
12:46
12:46
12:46
12:46
12:46
12:28
12:46
DL3526
DL1563
DL1563
15:54
15:54
15:54
15:54
15:54
16:09
15:54
DL4005
DL1563
DL1563
17:42
17:42
17:42
17:42
17:42
17:42
17:42
The timetable & schedule information was updated at 2026-04-22

There are two airlines with scheduled flights between YWG and ORD. United is the only airline with non-stop flights from Winnipeg International to Chicago O'Hare and the flight time is 2 hours and 34 minutes. You can also connect with Delta via Minneapolis with a flight time of 3 hours and 39 minutes.