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Flights from Winnipeg to Chicago (YWG to CHI)

Discover alternate routes & cheap one way flights from Winnipeg to Chicago (YWG to CHI) within a departure date range.

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CAD 214
8:35pm - 4:11pm
Tue May 16th
19h 36m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue May 16th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 8h 55m
Wed May 17th 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 2h 9m
Wed May 17th 2023 Spirit Airlines · NK 1704 Depart at 2:04pm from Orlando (MCO) Fly for 3h 7m Arrive at 4:11pm in Chicago (ORD)
CAD 214
8:35pm - 7:23pm
Tue May 2nd
22h 48m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue May 2nd 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 8h 55m
Wed May 3rd 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 5h 23m
Wed May 3rd 2023 Spirit Airlines · NK 322 Depart at 5:18pm from Orlando (MCO) Fly for 3h 5m Arrive at 7:23pm in Chicago (ORD)
CAD 215
8:35pm - 10:59pm
Tue May 9th
26h 24m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Tue May 9th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 8h 55m
Wed May 10th 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 9h 10m
Wed May 10th 2023 Frontier Airlines · F9 1020 Depart at 9:05pm from Orlando (MCO) Fly for 2h 54m Arrive at 10:59pm in Chicago (MDW)
CAD 215
8:35pm - 12:59am
Tue May 2nd
28h 24m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Tue May 2nd 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 8h 55m
Wed May 3rd 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 11h 10m
Wed May 3rd 2023 Frontier Airlines · F9 1024 Depart at 11:05pm from Orlando (MCO) Fly for 2h 54m Arrive at 12:59am in Chicago (MDW)
CAD 215
8:35pm - 12:59am
Tue May 9th
28h 24m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Tue May 9th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 8h 55m
Wed May 10th 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 11h 10m
Wed May 10th 2023 Frontier Airlines · F9 1024 Depart at 11:05pm from Orlando (MCO) Fly for 2h 54m Arrive at 12:59am in Chicago (MDW)
CAD 218
8:35pm - 7:17pm
Tue May 9th
22h 42m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue May 9th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 8h 55m
Wed May 10th 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 5h 15m
Wed May 10th 2023 Spirit Airlines · NK 322 Depart at 5:10pm from Orlando (MCO) Fly for 3h 7m Arrive at 7:17pm in Chicago (ORD)
CAD 223
9:05am - 2:19pm
Sun Apr 30th
53h 14m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Sun Apr 30th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 20h 25m
Mon May 1st 2023 Lynx Air · Y9 605 Depart at 9:00am from Toronto (YYZ) Fly for 2h 55m Arrive at 11:55am in Orlando (MCO)
Layover in Orlando for 24h 30m
Tue May 2nd 2023 Frontier Airlines · F9 1022 Depart at 12:25pm from Orlando (MCO) Fly for 2h 54m Arrive at 2:19pm in Chicago (MDW)
CAD 226
8:35pm - 9:33pm
Tue Apr 25th
24h 58m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue Apr 25th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 9h 5m
Wed Apr 26th 2023 Lynx Air · Y9 605 Depart at 9:10am from Toronto (YYZ) Fly for 3h 3m Arrive at 12:13pm in Orlando (MCO)
Layover in Orlando for 7h 15m
Wed Apr 26th 2023 Spirit Airlines · NK 2056 Depart at 7:28pm from Orlando (MCO) Fly for 3h 5m Arrive at 9:33pm in Chicago (ORD)
CAD 226
8:35pm - 2:08pm
Tue Apr 25th
41h 33m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue Apr 25th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 9h 5m
Wed Apr 26th 2023 Lynx Air · Y9 605 Depart at 9:10am from Toronto (YYZ) Fly for 3h 3m Arrive at 12:13pm in Orlando (MCO)
Layover in Orlando for 23h 50m
Thu Apr 27th 2023 Spirit Airlines · NK 1704 Depart at 12:03pm from Orlando (MCO) Fly for 3h 5m Arrive at 2:08pm in Chicago (ORD)
CAD 227
8:35pm - 7:23pm
Tue Apr 25th
22h 48m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue Apr 25th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 9h 5m
Wed Apr 26th 2023 Lynx Air · Y9 605 Depart at 9:10am from Toronto (YYZ) Fly for 3h 3m Arrive at 12:13pm in Orlando (MCO)
Layover in Orlando for 5h 5m
Wed Apr 26th 2023 Spirit Airlines · NK 322 Depart at 5:18pm from Orlando (MCO) Fly for 3h 5m Arrive at 7:23pm in Chicago (ORD)
CAD 252
7:45am - 2:38pm
Tue May 2nd
6h 53m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Air Canada · AC 372 Depart at 7:45am from Winnipeg (YWG) Fly for 2h 49m Arrive at 11:34am in Montreal (YUL)
Layover in Montreal for 1h 36m
Tue May 2nd 2023 Air Canada · AC 8963 Depart at 1:10pm from Montreal (YUL) Fly for 2h 28m Arrive at 2:38pm in Chicago (ORD)
CAD 255
5:30am - 1:20pm
Sat May 6th
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sat May 6th 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Sat May 6th 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 255
5:30am - 1:20pm
Tue May 16th
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 16th 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Tue May 16th 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 255
5:30am - 1:20pm
Tue May 2nd
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Tue May 2nd 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 259
5:30am - 1:20pm
Sat May 13th
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sat May 13th 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Sat May 13th 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 259
5:30am - 1:20pm
Tue May 9th
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Tue May 9th 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 259
5:30am - 1:20pm
Thu May 11th
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 11th 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Thu May 11th 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 259
5:30am - 1:20pm
Wed May 10th
7h 50m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 10th 2023 United Airlines · UA 8444 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 3h 36m
Wed May 10th 2023 United Airlines · UA 8694 Depart at 12:30pm from Toronto (YYZ) Fly for 1h 50m Arrive at 1:20pm in Chicago (ORD)
CAD 260
4:30pm - 10:17pm
Tue May 16th
5h 47m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 16th 2023 Air Canada · AC 268 Depart at 4:30pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 7:54pm in Toronto (YYZ)
Layover in Toronto for 1h 21m
Tue May 16th 2023 Air Canada · AC 4961 Depart at 9:15pm from Toronto (YYZ) Fly for 2h 2m Arrive at 10:17pm in Chicago (ORD)
CAD 271
9:05am - 4:02pm
Tue May 16th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 16th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Tue May 16th 2023 United Airlines · UA 5512 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 271
9:05am - 4:02pm
Tue May 16th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 16th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Tue May 16th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 271
3:40pm - 1:29am
Thu Apr 27th
9h 49m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Thu Apr 27th 2023 WestJet · WS 1346 Depart at 3:40pm from Winnipeg (YWG) Fly for 3h 56m Arrive at 8:36pm in Orlando (MCO)
Layover in Orlando for 2h 59m
Thu Apr 27th 2023 Frontier Airlines · F9 1024 Depart at 11:35pm from Orlando (MCO) Fly for 2h 54m Arrive at 1:29am in Chicago (MDW)
CAD 271
8:35pm - 7:20am
Tue May 16th
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 16th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Wed May 17th 2023 United Airlines · UA 8491 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 271
8:35pm - 7:20am
Sun May 14th
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sun May 14th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Mon May 15th 2023 United Airlines · UA 8491 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 271
8:35pm - 7:20am
Mon May 15th
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Mon May 15th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Tue May 16th 2023 United Airlines · UA 8491 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 276
9:05am - 4:02pm
Tue May 9th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Tue May 9th 2023 United Airlines · UA 5512 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 276
9:05am - 4:02pm
Wed May 10th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 10th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Wed May 10th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 276
8:35pm - 7:20am
Tue May 9th
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Wed May 10th 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 276
8:35pm - 7:20am
Fri May 12th
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri May 12th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Sat May 13th 2023 United Airlines · UA 8491 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 277
9:00am - 7:05pm
Thu Apr 27th
10h 5m
Winnipeg (YWG) → Chicago (RFD)
1 Stop
Thu Apr 27th 2023 Swoop · WO 772 Depart at 9:00am from Winnipeg (YWG) Fly for 3h 45m Arrive at 1:45pm in Orlando (SFB)
Layover in Orlando for 3h 33m
Thu Apr 27th 2023 Allegiant Air · G4 2962 Depart at 5:18pm from Orlando (SFB) Fly for 2h 47m Arrive at 7:05pm in Chicago (RFD)
CAD 278
12:37pm - 6:19pm
Mon May 8th
5h 42m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Mon May 8th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 44m
Mon May 8th 2023 Delta Air Lines · DL 3623 Depart at 4:45pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 6:19pm in Chicago (MDW)
CAD 278
12:45pm - 6:35pm
Wed May 3rd
5h 50m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Wed May 3rd 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 48m
Wed May 3rd 2023 Delta Air Lines · DL 3918 Depart at 4:57pm from Minneapolis (MSP) Fly for 1h 38m Arrive at 6:35pm in Chicago (MDW)
CAD 278
6:55am - 1:35pm
Sun May 14th
6h 40m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Sun May 14th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 3h 42m
Sun May 14th 2023 Delta Air Lines · DL 3635 Depart at 12:00pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 1:35pm in Chicago (MDW)
CAD 278
12:45pm - 7:44pm
Fri May 5th
6h 59m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri May 5th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 3h 56m
Fri May 5th 2023 Delta Air Lines · DL 1523 Depart at 6:05pm from Minneapolis (MSP) Fly for 1h 39m Arrive at 7:44pm in Chicago (ORD)
CAD 278
12:45pm - 7:44pm
Wed May 3rd
6h 59m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 3h 56m
Wed May 3rd 2023 Delta Air Lines · DL 1523 Depart at 6:05pm from Minneapolis (MSP) Fly for 1h 39m Arrive at 7:44pm in Chicago (ORD)
CAD 278
12:45pm - 11:48pm
Tue May 2nd
11h 3m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Tue May 2nd 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 4h 1m
Tue May 2nd 2023 Delta Air Lines · DL 1293 Depart at 6:10pm from Minneapolis (MSP) Fly for 2h 38m Arrive at 9:48pm in Atlanta (ATL)
Layover in Atlanta for 1h 7m
Tue May 2nd 2023 Delta Air Lines · DL 2377 Depart at 10:55pm from Atlanta (ATL) Fly for 1h 53m Arrive at 11:48pm in Chicago (MDW)
CAD 279
1:45pm - 10:17pm
Wed May 10th
8h 32m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 10th 2023 Lynx Air · Y9 523 Depart at 1:45pm from Winnipeg (YWG) Fly for 2h 29m Arrive at 5:14pm in Toronto (YYZ)
Layover in Toronto for 4h 1m
Wed May 10th 2023 Air Canada · AC 4961 Depart at 9:15pm from Toronto (YYZ) Fly for 2h 2m Arrive at 10:17pm in Chicago (ORD)
CAD 280
12:37pm - 4:50pm
Wed May 17th
4h 13m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 17th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 14m
Wed May 17th 2023 Delta Air Lines · DL 1506 Depart at 3:15pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 4:50pm in Chicago (ORD)
CAD 280
12:37pm - 6:19pm
Tue May 9th
5h 42m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Tue May 9th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 44m
Tue May 9th 2023 Delta Air Lines · DL 3623 Depart at 4:45pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 6:19pm in Chicago (MDW)
CAD 280
12:45pm - 6:35pm
Thu May 4th
5h 50m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Thu May 4th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 48m
Thu May 4th 2023 Delta Air Lines · DL 3918 Depart at 4:57pm from Minneapolis (MSP) Fly for 1h 38m Arrive at 6:35pm in Chicago (MDW)
CAD 280
6:55am - 12:52pm
Tue May 9th
5h 57m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Tue May 9th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 0h 40m
Tue May 9th 2023 Delta Air Lines · DL 2619 Depart at 8:58am from Minneapolis (MSP) Fly for 1h 42m Arrive at 11:40am in Detroit (DTW)
Layover in Detroit for 0h 55m
Tue May 9th 2023 Delta Air Lines · DL 3666 Depart at 12:35pm from Detroit (DTW) Fly for 1h 17m Arrive at 12:52pm in Chicago (MDW)
CAD 280
9:05am - 4:02pm
Tue May 9th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Tue May 9th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 280
8:35pm - 7:20am
Thu May 11th
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 11th 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Fri May 12th 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 281
6:55am - 1:35pm
Tue May 16th
6h 40m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Tue May 16th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 3h 42m
Tue May 16th 2023 Delta Air Lines · DL 3635 Depart at 12:00pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 1:35pm in Chicago (MDW)
CAD 282
12:45pm - 4:54pm
Tue May 2nd
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Tue May 2nd 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 282
12:37pm - 6:19pm
Wed May 10th
5h 42m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Wed May 10th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 44m
Wed May 10th 2023 Delta Air Lines · DL 3623 Depart at 4:45pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 6:19pm in Chicago (MDW)
CAD 282
12:45pm - 6:35pm
Tue May 2nd
5h 50m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Tue May 2nd 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 48m
Tue May 2nd 2023 Delta Air Lines · DL 3918 Depart at 4:57pm from Minneapolis (MSP) Fly for 1h 38m Arrive at 6:35pm in Chicago (MDW)
CAD 282
12:45pm - 6:35pm
Sun May 7th
5h 50m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Sun May 7th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 48m
Sun May 7th 2023 Delta Air Lines · DL 3918 Depart at 4:57pm from Minneapolis (MSP) Fly for 1h 38m Arrive at 6:35pm in Chicago (MDW)
CAD 282
6:55am - 1:41pm
Tue May 2nd
6h 46m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Tue May 2nd 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 25m Arrive at 8:20am in Minneapolis (MSP)
Layover in Minneapolis for 3h 42m
Tue May 2nd 2023 Delta Air Lines · DL 3919 Depart at 12:02pm from Minneapolis (MSP) Fly for 1h 39m Arrive at 1:41pm in Chicago (MDW)
CAD 282
12:45pm - 7:44pm
Mon May 1st
6h 59m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Mon May 1st 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 3h 56m
Mon May 1st 2023 Delta Air Lines · DL 1523 Depart at 6:05pm from Minneapolis (MSP) Fly for 1h 39m Arrive at 7:44pm in Chicago (ORD)
CAD 284
12:37pm - 4:50pm
Thu May 11th
4h 13m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 11th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 14m
Thu May 11th 2023 Delta Air Lines · DL 1506 Depart at 3:15pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 4:50pm in Chicago (ORD)
CAD 284
12:37pm - 4:50pm
Sun May 14th
4h 13m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sun May 14th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 14m
Sun May 14th 2023 Delta Air Lines · DL 1506 Depart at 3:15pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 4:50pm in Chicago (ORD)
CAD 285
12:37pm - 4:50pm
Tue May 9th
4h 13m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 14m
Tue May 9th 2023 Delta Air Lines · DL 1506 Depart at 3:15pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 4:50pm in Chicago (ORD)
CAD 285
6:55am - 1:11pm
Tue May 9th
6h 16m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Tue May 9th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 0h 40m
Tue May 9th 2023 Delta Air Lines · DL 2619 Depart at 8:58am from Minneapolis (MSP) Fly for 1h 42m Arrive at 11:40am in Detroit (DTW)
Layover in Detroit for 1h 10m
Tue May 9th 2023 Delta Air Lines · DL 1019 Depart at 12:50pm from Detroit (DTW) Fly for 1h 21m Arrive at 1:11pm in Chicago (ORD)
CAD 287
12:37pm - 4:50pm
Wed May 10th
4h 13m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 10th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 14m
Wed May 10th 2023 Delta Air Lines · DL 1506 Depart at 3:15pm from Minneapolis (MSP) Fly for 1h 35m Arrive at 4:50pm in Chicago (ORD)
CAD 291
6:20am - 5:07pm
Sat May 6th
10h 47m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sat May 6th 2023 Air Canada · AC 8331 Depart at 6:20am from Winnipeg (YWG) Fly for 2h 5m Arrive at 7:25am in Calgary (YYC)
Layover in Calgary for 5h 17m
Sat May 6th 2023 Air Canada · AC 4026 Depart at 12:42pm from Calgary (YYC) Fly for 3h 25m Arrive at 5:07pm in Chicago (ORD)
CAD 294
5:30am - 2:50pm
Wed May 3rd
9h 20m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Air Canada · AC 256 Depart at 5:30am from Winnipeg (YWG) Fly for 2h 24m Arrive at 8:54am in Toronto (YYZ)
Layover in Toronto for 5h 6m
Wed May 3rd 2023 Air Canada · AC 8909 Depart at 2:00pm from Toronto (YYZ) Fly for 1h 50m Arrive at 2:50pm in Chicago (ORD)
CAD 294
8:25pm - 7:20am
Tue May 2nd
10h 55m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Air Canada · AC 270 Depart at 8:25pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 11:49pm in Toronto (YYZ)
Layover in Toronto for 6h 41m
Wed May 3rd 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 294
8:25pm - 7:20am
Wed May 3rd
10h 55m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Air Canada · AC 270 Depart at 8:25pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 11:49pm in Toronto (YYZ)
Layover in Toronto for 6h 41m
Thu May 4th 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 294
8:25pm - 7:20am
Fri May 5th
10h 55m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri May 5th 2023 Air Canada · AC 270 Depart at 8:25pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 11:49pm in Toronto (YYZ)
Layover in Toronto for 6h 41m
Sat May 6th 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 294
8:25pm - 7:20am
Sat May 6th
10h 55m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sat May 6th 2023 Air Canada · AC 270 Depart at 8:25pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 11:49pm in Toronto (YYZ)
Layover in Toronto for 6h 41m
Sun May 7th 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 294
8:25pm - 8:50am
Wed May 3rd
12h 25m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Air Canada · AC 270 Depart at 8:25pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 11:49pm in Toronto (YYZ)
Layover in Toronto for 8h 11m
Thu May 4th 2023 Air Canada · AC 8903 Depart at 8:00am from Toronto (YYZ) Fly for 1h 50m Arrive at 8:50am in Chicago (ORD)
CAD 299
1:40pm - 10:17pm
Tue May 9th
8h 37m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 Lynx Air · Y9 515 Depart at 1:40pm from Winnipeg (YWG) Fly for 2h 29m Arrive at 5:09pm in Toronto (YYZ)
Layover in Toronto for 4h 6m
Tue May 9th 2023 United Airlines · UA 3640 Depart at 9:15pm from Toronto (YYZ) Fly for 2h 2m Arrive at 10:17pm in Chicago (ORD)
CAD 299
1:40pm - 10:17pm
Tue May 9th
8h 37m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 9th 2023 Lynx Air · Y9 515 Depart at 1:40pm from Winnipeg (YWG) Fly for 2h 29m Arrive at 5:09pm in Toronto (YYZ)
Layover in Toronto for 4h 6m
Tue May 9th 2023 Air Canada · AC 4961 Depart at 9:15pm from Toronto (YYZ) Fly for 2h 2m Arrive at 10:17pm in Chicago (ORD)
CAD 299
8:25pm - 7:20am
Sun May 7th
10h 55m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sun May 7th 2023 Air Canada · AC 270 Depart at 8:25pm from Winnipeg (YWG) Fly for 2h 24m Arrive at 11:49pm in Toronto (YYZ)
Layover in Toronto for 6h 41m
Mon May 8th 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 308
12:45pm - 12:59am
Tue Apr 25th
12h 14m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Tue Apr 25th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 6m
Tue Apr 25th 2023 Delta Air Lines · DL 1565 Depart at 4:15pm from Minneapolis (MSP) Fly for 3h 19m Arrive at 8:34pm in Orlando (MCO)
Layover in Orlando for 2h 31m
Tue Apr 25th 2023 Frontier Airlines · F9 1024 Depart at 11:05pm from Orlando (MCO) Fly for 2h 54m Arrive at 12:59am in Chicago (MDW)
CAD 311
12:45pm - 12:59am
Wed Apr 26th
12h 14m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Wed Apr 26th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 6m
Wed Apr 26th 2023 Delta Air Lines · DL 1565 Depart at 4:15pm from Minneapolis (MSP) Fly for 3h 19m Arrive at 8:34pm in Orlando (MCO)
Layover in Orlando for 2h 31m
Wed Apr 26th 2023 Frontier Airlines · F9 1024 Depart at 11:05pm from Orlando (MCO) Fly for 2h 54m Arrive at 12:59am in Chicago (MDW)
CAD 319
9:00am - 7:05pm
Sun Apr 30th
10h 5m
Winnipeg (YWG) → Chicago (RFD)
1 Stop
Sun Apr 30th 2023 Swoop · WO 772 Depart at 9:00am from Winnipeg (YWG) Fly for 3h 45m Arrive at 1:45pm in Orlando (SFB)
Layover in Orlando for 3h 33m
Sun Apr 30th 2023 Allegiant Air · G4 2822 Depart at 5:18pm from Orlando (SFB) Fly for 2h 47m Arrive at 7:05pm in Chicago (RFD)
CAD 323
6:00am - 4:25pm
Sat May 6th
10h 25m
Winnipeg (YWG) → Chicago (ORD)
2 Stops
Sat May 6th 2023 Delta Air Lines · DL 7151 Depart at 6:00am from Winnipeg (YWG) Fly for 2h 21m Arrive at 9:21am in Toronto (YYZ)
Layover in Toronto for 2h 39m
Sat May 6th 2023 Delta Air Lines · DL 4849 Depart at 12:00pm from Toronto (YYZ) Fly for 1h 15m Arrive at 1:15pm in Detroit (DTW)
Layover in Detroit for 2h 45m
Sat May 6th 2023 Delta Air Lines · DL 1568 Depart at 4:00pm from Detroit (DTW) Fly for 1h 25m Arrive at 4:25pm in Chicago (ORD)
CAD 327
9:05am - 4:02pm
Mon May 15th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Mon May 15th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Mon May 15th 2023 United Airlines · UA 5512 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 327
9:05am - 4:02pm
Wed May 17th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 17th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Wed May 17th 2023 United Airlines · UA 5512 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 327
9:05am - 4:02pm
Wed May 17th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 17th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Wed May 17th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 327
8:35pm - 7:20am
Tue May 2nd
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Wed May 3rd 2023 United Airlines · UA 8491 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 330
9:05am - 4:02pm
Mon May 15th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Mon May 15th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Mon May 15th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 330
8:35pm - 7:20am
Tue May 2nd
10h 45m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Flair Airlines · F8 640 Depart at 8:35pm from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:05am in Toronto (YYZ)
Layover in Toronto for 6h 25m
Wed May 3rd 2023 Air Canada · AC 8901 Depart at 6:30am from Toronto (YYZ) Fly for 1h 50m Arrive at 7:20am in Chicago (ORD)
CAD 338
12:37pm - 6:19pm
Sun May 14th
5h 42m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Sun May 14th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 44m
Sun May 14th 2023 Delta Air Lines · DL 3623 Depart at 4:45pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 6:19pm in Chicago (MDW)
CAD 338
12:37pm - 6:19pm
Thu May 11th
5h 42m
Winnipeg (YWG) → Chicago (MDW)
1 Stop
Thu May 11th 2023 Delta Air Lines · DL 2257 Depart at 12:37pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:01pm in Minneapolis (MSP)
Layover in Minneapolis for 2h 44m
Thu May 11th 2023 Delta Air Lines · DL 3623 Depart at 4:45pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 6:19pm in Chicago (MDW)
CAD 338
6:55am - 12:52pm
Fri May 12th
5h 57m
Winnipeg (YWG) → Chicago (MDW)
2 Stops
Fri May 12th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 0h 40m
Fri May 12th 2023 Delta Air Lines · DL 2619 Depart at 8:58am from Minneapolis (MSP) Fly for 1h 42m Arrive at 11:40am in Detroit (DTW)
Layover in Detroit for 0h 55m
Fri May 12th 2023 Delta Air Lines · DL 3666 Depart at 12:35pm from Detroit (DTW) Fly for 1h 17m Arrive at 12:52pm in Chicago (MDW)
CAD 338
9:05am - 4:02pm
Wed May 3rd
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Wed May 3rd 2023 United Airlines · UA 5493 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 338
9:05am - 4:02pm
Tue May 2nd
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Tue May 2nd 2023 United Airlines · UA 5493 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 339
9:05am - 6:32pm
Sat May 6th
9h 27m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sat May 6th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 4h 55m
Sat May 6th 2023 United Airlines · UA 5515 Depart at 5:30pm from Toronto (YYZ) Fly for 2h 2m Arrive at 6:32pm in Chicago (ORD)
CAD 340
6:55am - 11:28am
Tue May 16th
4h 33m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 16th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 1h 42m
Tue May 16th 2023 Delta Air Lines · DL 1501 Depart at 10:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 11:28am in Chicago (ORD)
CAD 341
9:05am - 4:02pm
Wed May 3rd
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Wed May 3rd 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 341
9:05am - 4:02pm
Tue May 2nd
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue May 2nd 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Tue May 2nd 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 344
6:55am - 11:28am
Sun May 14th
4h 33m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sun May 14th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 1h 42m
Sun May 14th 2023 Delta Air Lines · DL 1501 Depart at 10:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 11:28am in Chicago (ORD)
CAD 348
9:05am - 6:32pm
Sat May 6th
9h 27m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sat May 6th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 4h 55m
Sat May 6th 2023 Air Canada · AC 4990 Depart at 5:30pm from Toronto (YYZ) Fly for 2h 2m Arrive at 6:32pm in Chicago (ORD)
CAD 349
6:55am - 11:28am
Thu May 11th
4h 33m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 11th 2023 Delta Air Lines · DL 1283 Depart at 6:55am from Winnipeg (YWG) Fly for 1h 23m Arrive at 8:18am in Minneapolis (MSP)
Layover in Minneapolis for 1h 42m
Thu May 11th 2023 Delta Air Lines · DL 1501 Depart at 10:00am from Minneapolis (MSP) Fly for 1h 28m Arrive at 11:28am in Chicago (ORD)
CAD 360
9:05am - 4:02pm
Thu May 4th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 4th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Thu May 4th 2023 United Airlines · UA 5493 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 363
9:05am - 4:02pm
Thu May 4th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 4th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Thu May 4th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 366
9:05am - 4:02pm
Fri May 12th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri May 12th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Fri May 12th 2023 United Airlines · UA 5512 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 370
9:05am - 4:02pm
Fri May 12th
6h 57m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri May 12th 2023 Flair Airlines · F8 642 Depart at 9:05am from Winnipeg (YWG) Fly for 2h 30m Arrive at 12:35pm in Toronto (YYZ)
Layover in Toronto for 2h 25m
Fri May 12th 2023 Air Canada · AC 5137 Depart at 3:00pm from Toronto (YYZ) Fly for 2h 2m Arrive at 4:02pm in Chicago (ORD)
CAD 386
12:45pm - 4:54pm
Wed May 3rd
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed May 3rd 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Wed May 3rd 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 387
12:45pm - 4:54pm
Thu May 4th
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Thu May 4th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Thu May 4th 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 408
12:45pm - 4:54pm
Mon May 1st
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Mon May 1st 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Mon May 1st 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 419
12:45pm - 4:54pm
Sun May 7th
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sun May 7th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Sun May 7th 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 498
12:45pm - 4:54pm
Fri Apr 28th
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri Apr 28th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Fri Apr 28th 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 531
12:45pm - 4:54pm
Wed Apr 26th
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Wed Apr 26th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Wed Apr 26th 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 531
12:45pm - 4:54pm
Tue Apr 25th
4h 9m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Tue Apr 25th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 11m
Tue Apr 25th 2023 Delta Air Lines · DL 1506 Depart at 3:20pm from Minneapolis (MSP) Fly for 1h 34m Arrive at 4:54pm in Chicago (ORD)
CAD 831
12:45pm - 4:49pm
Fri May 5th
4h 4m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Fri May 5th 2023 WestJet · WS 6338 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 10m
Fri May 5th 2023 United Airlines · UA 572 Depart at 3:19pm from Minneapolis (MSP) Fly for 1h 30m Arrive at 4:49pm in Chicago (ORD)
CAD 909
12:45pm - 4:49pm
Sun May 7th
4h 4m
Winnipeg (YWG) → Chicago (ORD)
1 Stop
Sun May 7th 2023 Delta Air Lines · DL 2257 Depart at 12:45pm from Winnipeg (YWG) Fly for 1h 24m Arrive at 2:09pm in Minneapolis (MSP)
Layover in Minneapolis for 1h 10m
Sun May 7th 2023 United Airlines · UA 572 Depart at 3:19pm from Minneapolis (MSP) Fly for 1h 30m Arrive at 4:49pm in Chicago (ORD)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Andy Travels

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Flights from Winnipeg to Chicago (YWG to CHI)

Sarah Belizaire

John Ford

Andy Travels

Travel With Bender

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