Cheap flights to Oregon from Chicago

Round trips from Chicago from $461. Cheapest dates, deal ratings and where to book.

• Portland: $461, 2026-10-16 to 2026-10-20
• Medford: $545, 2026-10-22 to 2026-10-26

Nearby

• Washington
• Idaho
• Nevada
• California
• Utah
• Montana
• Wyoming
• Arizona