Flights from Winnipeg to Chicago from $ 549*
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1 Passenger, Economy
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today
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Featured daily fares for flights from Winnipeg (YWG) to Chicago (ORD)
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More United deals on Winnipeg (YWG) to Chicago (ORD) flights
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 01/08/26 - 01/23/26 | from $Â 549 Viewed: 9 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 01/08/26 - 01/23/26 | from $Â 566 Viewed: 9 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 01/08/26 - 01/23/26 | from $Â 671 Viewed: 9 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 12/23/25 - 12/30/25 | from $Â 692 Viewed: 11 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 12/23/25 - 12/30/25 | from $Â 748 Viewed: 11 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 01/08/26 - 01/23/26 | from $Â 766 Viewed: 9 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 12/23/25 - 12/30/25 | from $Â 868 Viewed: 11 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 01/08/26 - 01/23/26 | from $Â 888 Viewed: 9 hours ago |
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.
