American Airlines flies from Chicago O'Hare Airport (ORD) to Galena 3 times a day. Alternatively, Chicago Transit (CTA) operates a bus from Chicago O'Hare Airport (ORD) to Galena every 10 minutes. Tickets cost $2 - $3 and the journey takes 7 min. Burlington Trailways also services this route once daily.
From Chicago O'Hare airport fly to Dubuque airport then taxi to Galena. 1 h 26 min $364. From O'Hare subway to Chicago Cumberland Ave, IL then bus to Galena. 4 h 22 min $47. From Chicago O'Hare Airport (ORD) drive to Galena. 3 h 3 min $18.