Flights from Winnipeg to Chicago from $ 676*
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1 Passenger, Economy
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today
today
Featured daily fares for flights from Winnipeg (YWG) to Chicago (ORD)
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Try alternate month or interact with individual days below in order to find offers.
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 | 08/13/26 - 08/16/26 | from $ 676 Viewed: 4 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 08/13/26 - 08/16/26 | from $ 745 Viewed: 4 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 08/20/26 - 08/23/26 | from $ 745 Viewed: 50 minutes ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 08/20/26 - 08/23/26 | from $ 823 Viewed: 50 minutes ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 06/15/26 - 06/18/26 | from $ 880 Viewed: 1 hour ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 08/13/26 - 08/16/26 | from $ 887 Viewed: 4 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | Roundtrip | Economy | 06/15/26 - 06/18/26 | from $ 958 Viewed: 1 hour 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.
