Find Winnipeg to Chicago flights starting at CAD 182.
Book one-way or return flights from Winnipeg to Chicago from as little as CAD 182. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- YWG08:009h 27m1 stopORD17:27Wed, May 8|Winnipeg - Chicago|WestJetCAD 182CAD 33145% OFF45% OFFCAD 331CAD 182
- YWG17:0026h 58m1 stopORD19:58Fri, May 17|Winnipeg - Chicago|WestJetCAD 197CAD 33141% OFF41% OFFCAD 331CAD 197
- YWG08:006h 39m1 stopMDW14:39Wed, May 15|Winnipeg - Chicago|WestJetCAD 197CAD 33140% OFF40% OFFCAD 331CAD 197
- YWG17:0018h 29m1 stopORD11:29Fri, May 10|Winnipeg - Chicago|WestJetCAD 200CAD 200
- YWG08:006h 41m1 stopMDW14:41Wed, May 29|Winnipeg - Chicago|WestJetCAD 202CAD 202
- YWG17:009h1 stopORD02:00Fri, May 31|Winnipeg - Chicago|WestJetCAD 217CAD 217
- YWG08:0014h 3m1 stopORD22:03Mon, May 20|Winnipeg - Chicago|WestJetCAD 220CAD 220
- YWG08:008h 37m1 stopORD16:37Wed, May 22|Winnipeg - Chicago|WestJetCAD 226CAD 226
- YWG08:0010h 34m1 stopORD18:34Thu, Jul 11|Winnipeg - Chicago|WestJetCAD 226CAD 226
- YWG08:308h 35m1 stopORD17:05Fri, May 24|Winnipeg - Chicago|WestJetCAD 228CAD 228
- YWG13:003h 5mDirectCHI14:00Sat, May 11|Winnipeg - Chicago|WestJetFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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- CheapestYWG08:009h 27m1 transferORD17:27Winnipeg James Armstrong Richardson International Airport - O'Hare International AirportWed, May 8WestJetCAD 182
- YWG08:006h 39m1 transferMDW14:39Winnipeg James Armstrong Richardson International Airport - Midway International AirportWed, May 8WestJetCAD 184
- YWG08:006h 39m1 transferMDW14:39Winnipeg James Armstrong Richardson International Airport - Midway International AirportWed, May 8WestJetCAD 184Find More Flights
How do I find the cheapest flights?
How to find a cheap flight from Winnipeg to Chicago
Cheapest direct flight price | CAD 182 |
---|---|
Cheapest return ticket price | CAD 454 |
Cheapest month | February |
Peak season for travel | July |
Flight distance | 1,154.29km |
Popular airline | United Airlines |
Plan Your Trip Around Chicago
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