Cheap flights from Winnipeg to Chicago

Find cheap Chicago to Winnipeg flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Winnipeg.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Winnipeg to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Winnipeg (YWG) - Chicago (CHI) 2024-09-08 2024-09-10 253 USD 47 hours 8 minutes Connection 2024-05-16T19:34:05
Winnipeg (YWG) - Chicago (CHI) 2024-10-01 2024-10-02 273 USD 43 hours 53 minutes Connection 2024-05-16T03:06:12
Winnipeg (YWG) - Chicago (CHI) 2024-05-27 2024-06-01 290 USD 26 hours 22 minutes Connection 2024-05-15T19:17:19
Winnipeg (YWG) - Chicago (CHI) 2024-05-24 2024-05-27 316 USD 47 hours 48 minutes Connection 2024-05-16T19:50:08
Winnipeg (YWG) - Chicago (CHI) 2024-06-18 2024-06-22 317 USD 17 hours 47 minutes Connection 2024-05-16T21:32:56
Winnipeg (YWG) - Chicago (CHI) 2024-06-18 2024-07-10 324 USD 17 hours 49 minutes Connection 2024-05-15T13:05:53
Winnipeg (YWG) - Chicago (CHI) 2024-06-04 2024-06-11 325 USD 24 hours 19 minutes Connection 2024-05-15T03:12:39
Winnipeg (YWG) - Chicago (CHI) 2024-05-29 2024-06-01 330 USD 17 hours 52 minutes Connection 2024-05-15T12:37:44
Winnipeg (YWG) - Chicago (CHI) 2024-08-19 2024-08-23 338 USD 17 hours 49 minutes Connection 2024-05-17T13:31:02
Winnipeg (YWG) - Chicago (CHI) 2024-05-25 2024-05-26 340 USD 20 hours 0 minutes Connection 2024-05-17T16:25:56
Winnipeg (YWG) - Chicago (CHI) 2024-07-01 2024-07-24 341 USD 17 hours 47 minutes Connection 2024-05-16T01:40:06
Winnipeg (YWG) - Chicago (CHI) 2024-07-01 2024-07-23 343 USD 17 hours 47 minutes Connection 2024-05-17T15:36:15
Winnipeg (YWG) - Chicago (CHI) 2024-07-01 2024-07-20 347 USD 19 hours 44 minutes Connection 2024-05-16T19:10:38
Winnipeg (YWG) - Chicago (CHI) 2024-07-11 2024-07-15 347 USD 12 hours 9 minutes Connection 2024-05-15T19:06:19
Winnipeg (YWG) - Chicago (CHI) 2024-05-27 2024-05-28 353 USD 42 hours 0 minutes Connection 2024-05-17T18:48:56
Winnipeg (YWG) - Chicago (CHI) 2024-05-22 2024-05-27 358 USD 42 hours 33 minutes Connection 2024-05-15T16:14:38
Winnipeg (YWG) - Chicago (CHI) 2024-07-09 2024-07-15 361 USD 20 hours 42 minutes Connection 2024-05-16T08:50:04
Winnipeg (YWG) - Chicago (CHI) 2024-08-14 2024-08-19 361 USD 12 hours 16 minutes Connection 2024-05-15T14:30:51
Winnipeg (YWG) - Chicago (CHI) 2024-07-09 2024-07-20 367 USD 22 hours 39 minutes Connection 2024-05-16T08:57:52
Winnipeg (YWG) - Chicago (CHI) 2024-06-03 2024-06-11 369 USD 17 hours 40 minutes Connection 2024-05-15T04:32:56
Winnipeg (YWG) - Chicago (CHI) 2024-05-31 2024-06-03 370 USD 18 hours 20 minutes Connection 2024-05-17T14:24:43
Winnipeg (YWG) - Chicago (CHI) 2024-06-10 2024-06-12 374 USD 17 hours 55 minutes Connection 2024-05-15T15:24:15
Winnipeg (YWG) - Chicago (CHI) 2024-05-27 2024-05-30 380 USD 22 hours 56 minutes Connection 2024-05-15T01:19:42
Winnipeg (YWG) - Chicago (CHI) 2024-07-17 2024-07-24 383 USD 18 hours 49 minutes Connection 2024-05-17T15:34:59
Winnipeg (YWG) - Chicago (CHI) 2024-08-27 2024-08-30 383 USD 17 hours 49 minutes Connection 2024-05-17T04:58:00
Winnipeg (YWG) - Chicago (CHI) 2024-07-11 2024-07-14 384 USD 25 hours 26 minutes Connection 2024-05-15T19:06:19
Winnipeg (YWG) - Chicago (CHI) 2024-07-23 2024-08-14 385 USD 22 hours 38 minutes Connection 2024-05-17T15:35:53
Winnipeg (YWG) - Chicago (CHI) 2024-06-29 2024-07-03 386 USD 17 hours 49 minutes Connection 2024-05-15T21:56:05
Winnipeg (YWG) - Chicago (CHI) 2024-06-01 2024-06-26 391 USD 17 hours 57 minutes Connection 2024-05-17T12:32:28
Winnipeg (YWG) - Chicago (CHI) 2024-05-27 2024-06-19 391 USD 17 hours 40 minutes Connection 2024-05-18T05:09:05

Winnipeg to Chicago flight status

Flight Origin Destination Departure Arrival Equip
AC3215 Winnipeg (YWG) Chicago (ORD) 7:46 a.m. 9:51 a.m. ERJ 135 / ERJ 140 / ERJ 145
AC3570 Winnipeg (YWG) Chicago (ORD) 9:50 a.m. 12:45 p.m. E145
AC3506 Winnipeg (YWG) Chicago (ORD) 11:15 a.m. 2:06 p.m. ERJ 135 / ERJ 140 / ERJ 145
NZ9850 Winnipeg (YWG) Chicago (ORD) 11:30 p.m. 9:35 a.m. B739
OO5891 Winnipeg (YWG) Chicago (ORD) 5:43 p.m. 6:36 p.m. CRJ2
AY3272 Winnipeg (YWG) Chicago (ORD) 11:25 p.m. 1:05 a.m. 321
OO5953 Winnipeg (YWG) Chicago (ORD) 6:10 p.m. 7:40 p.m. CRJ2
NZ9846 Winnipeg (YWG) Chicago (ORD) 5:31 p.m. 8:16 p.m. 737-900
WQ2550 Winnipeg (YWG) Chicago (ORD) 11 p.m. None B734
NZ9848 Winnipeg (YWG) Chicago (ORD) 1:32 p.m. 3:59 p.m. A320-100/200
EI6456 Winnipeg (YWG) Chicago (ORD) 1:32 p.m. 3:59 p.m.
EI6455 Winnipeg (YWG) Chicago (ORD) 7:18 a.m. 10 a.m. CRJ
CM1508 Winnipeg (YWG) Chicago (ORD) 7:18 a.m. 10 a.m. E70
EV5970 Winnipeg (YWG) Chicago (ORD) 7:51 a.m. 9:59 a.m. ERJ
EI6457 Winnipeg (YWG) Chicago (ORD) 11:49 a.m. 2:10 p.m. CRJ
EI6458 Winnipeg (YWG) Chicago (ORD) 7:05 a.m. 9:40 a.m. ERJ 135 / ERJ 140 / ERJ 145
MI5096 Winnipeg (YWG) Chicago (ORD) noon 2:30 p.m. 320
IB6774 Winnipeg (YWG) Chicago (ORD) 8:10 a.m. 10:23 a.m.
AV2179 Winnipeg (YWG) Chicago (ORD) 5:37 p.m. 8:10 p.m.