Cheap flights from Winnipeg to Chicago

Cheapest current fares: $314 in May 2026, 1,137 km direct flight in ~1h 20m.

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Live fares · YWG → ORD

Cheapest month-by-month fares

Lowest available fare per calendar month from Winnipeg (YWG) to Chicago (ORD). Refreshed daily.

Winnipeg (YWG) → Chicago (ORD)

  1. May 2026 $314

Frequently asked questions

  • What is the cheapest month to fly from Winnipeg to Chicago?

    Based on current 6-month forward fare data, May 2026 is the cheapest month to fly from Winnipeg (YWG) to Chicago (ORD), with fares starting from $314.

  • What is the lowest current fare from YWG to ORD?

    The lowest currently-listed fare from Winnipeg (YWG) to Chicago (ORD) is $314 on 2026-05-30.

  • How long is the flight from Winnipeg to Chicago?

    Direct flights from YWG to ORD cover approximately 1,137 km (706 miles), with an estimated flight time of 1h 20m. Operating airlines: UA.

Related guides for this route

Sibling pages — full route detail, airport overviews, visa context, per-airline routes.

Full route page: YWG → ORD Cheapest month to fly to Chicago All flights from Winnipeg All flights to Chicago Flights to USA Visa-free with Canada passport UA routes