- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Plan, book, fly with confidence
WestJet flights from Winnipeg to Chicago (YWG→ORD)
Prices were available within the past 7 days and start at CA $258 for one-way flights and CA $447 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon., Mar. 10 - Mon., Mar. 17
YWG
Winnipeg
ORD
Chicago
CA $447 Roundtrip, found 4 days ago
CA $447
Roundtrip
found 4 days ago
Thu., Apr. 10 - Sun., Apr. 13
YWG
Winnipeg
ORD
Chicago
CA $490 Roundtrip, found 3 days ago
CA $490
Roundtrip
found 3 days ago
Wed., Mar. 12 - Mon., Mar. 17
YWG
Winnipeg
ORD
Chicago
CA $501 Roundtrip, found 4 days ago
CA $501
Roundtrip
found 4 days ago
Sat., May 24 - Tue., May 27
YWG
Winnipeg
ORD
Chicago
CA $524 Roundtrip, found 1 day ago
CA $524
Roundtrip
found 1 day ago
Origin airport | Winnipeg James Armstrong Richardson Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | Air Canada, Delta, United, WestJet |
Roundtrip price | CA $447 |
Distance | 1130 km |
- Trending WestJet Flights
- Trending Routes
- Other Airlines
- Main Airports for WestJet Flights
- Flights from Other Cities
- Expedia's Latest Trends
Most Popular WestJet Routes from Winnipeg
Most Popular WestJet Routes from Chicago
- Calgary to Toronto (YYC - YYZ)
- Abbotsford to Calgary (YXX - YYC)
- Vancouver to Toronto (YVR - YYZ)
- Toronto to Newark Liberty Intl. Airport (YYZ - EWR)
- Toronto to Las Vegas (YYZ - LAS)
- Toronto to Fort Lauderdale (YYZ - FLL)
- Vancouver to Las Vegas (YVR - LAS)
- Toronto to Orlando (YYZ - MCO)
- Toronto to Los Angeles (YYZ - LAX)
- Toronto to Las Vegas (YYZ - LAS)
Popular Domestic Routes in O'Hare Intl.
- Abbotsford to Calgary (YXX - YYC)
- Vancouver to Toronto (YVR - YYZ)
- Vancouver to Los Angeles (YVR - LAX)
- Toronto to Orlando (YYZ - MCO)
- Toronto to Calgary (YYZ - YYC)
- Toronto to Vancouver (YYZ - YVR)
- Toronto to Vancouver (YYZ - YVR)
- Vancouver to Toronto (YVR - YYZ)
- Edmonton to Abbotsford (YEG - YXX)
- Toronto to Los Angeles (YYZ - LAX)
Main Airports for WestJet Flights
Flights
Flights from Winnipeg to Flin FlonFlights from Calgary to ChurchillFlights from Toronto to ThompsonFlights from Vancouver to ChurchillFlights from Calgary to BrandonFlights from Thompson to WinnipegFlights from Winnipeg to ChurchillFlights from Brandon to CalgaryFlights from Brandon to SaskatoonFlights from Calgary to ThompsonFlights from Winnipeg to BrandonFlights from Montreal to ChurchillFlights from Winnipeg to DauphinFlights from Brandon to VancouverFlights from Brandon to EdmontonFlights from Brandon to WinnipegFlights from Toronto to ChurchillFlights from Toronto to BrandonCalm Air International Winnipeg (YWG) to Thompson (YTH) flightsFlights from Edmonton to ChurchillFlights from Winnipeg to ThompsonFlights from Thompson to ChurchillFlights from Ottawa to ChurchillFlights from Toronto to ChampaignFlights from Churchill to WinnipegFlights from Winnipeg to The PasFlights from Vancouver to BrandonFlights from The Pas to WinnipegFlights from Edmonton to BrandonFlights from Brandon to Toronto
*Available to Expedia members.