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

United Airlines

Non-stop with United Airlines

  • Total flight time: 2 hours and 34 minutes
  • Chicago is a United Airlines hub (Largest hub ).
  • 14 flights per week
  • Embraer 175 (Enhanced Winglets)
  • First class available
YWG
Direct
ORD

The timetable & schedule information was updated at 2026-04-22

Delta Air Lines

Via Minneapolis with Delta Air Lines

  • Total flight time: 3h 39m - 7h 58m.
  • Sky Team Alliance
  • 74 flights per week
YWG
 
Via MSP
 
ORD
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL3660
DL1567
06:40
06:40
06:40
06:40
06:40
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06:40
DL3660
DL4767
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06:40
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DL3871
DL1306
12:46
12:46
12:46
12:46
12:46
12:28
12:46
DL3526
DL1563
15:54
15:54
15:54
15:54
15:54
16:09
15:54
DL4005
DL1563
17:42
17:42
17:42
17:42
17:42
17:42
17:42
SHOW RETURN SCHEDULE
CHECK PRICES FOR YWG - ORD

The timetable & schedule information was updated at 2026-04-22

Staying up-to-date with the airlines

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Flight data on this page was last updated on 2026-06-02