Chicago, Illinois to Oregon, United States flights

Deals to Portland, Oregon are as low as $193 right now.
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Best Deals from CHI to Oregon

Discover the cheapest current deals from 764 recent searches matching your trip
  • $241
    Portland, Oregon
    2 days in Dec
    Sat
    8
    Mon
    10
  • $263
    Portland, Oregon
    3 days in Feb
    Thu
    7
    Sun
    10
  • $241
    Portland, Oregon
    4 days in Dec
    Thu
    6
    Mon
    10
  • $241
    Portland, Oregon
    5 days in Jan
    Thu
    10
    Tue
    15
  • $241
    Portland, Oregon
    5 days in Jan
    Thu
    17
    Tue
    22
  • $285
    Portland, Oregon
    2 days in May
    Fri
    10
    Sun
    12
  • When to Fly
    Prices range from $249 in February to $448 in October
  • Portland, Oregon
    $193
    This is a great deal at 38% off
  • Medford, Oregon
    $329
    This is a good deal at 23% off
  • Redmond/Bend, Oregon
    $339
    This is a great deal at 27% off
  • Eugene, Oregon
    $357
    This is a good deal at 17% off
  • North Bend, Oregon
    $760
    This is the best available price
  • From:
    Chicago, Illinois (MDW,ORD,RFD)
        
    To:
    Oregon, United States (7 Airports)    
        
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