The Galena–Chicago trail was a stagecoach route located in northern Illinois that ran from the mid-to-late 1830s until 1854. As indicated by its name, the route linked Chicago, located in the northeast of the state, with Galena which was located in the northwest. The Chicago-Galena trail includes the "Stagecoach Trail" that runs between Galena and Lena, Illinois.
The line traced its beginnings to as early as 1835 as a series of smaller trails, all operated by distinct stagecoach owners. A single trail linking Chicago to Galena was formally established in 1839 by John Frink and Martin Walker, who later established Frink, Walker & Company in 1840. Frink & Walker expanded their pre-existing trail from Chicago to Galena, putting a competing Chicago-Freeport stagecoach line run by J.D. Winters out of business. Frink & Walker ran two daily coaches that carried mail, passengers and small parcels from Chicago to Galena.