There were dirt roads in all directions. But rain would turn these roads into mud, making transportation very difficult.
Plank roads were an early solution. Built as toll roads, there there was a row of heavy stringers on each side of a 16-foot roadway and across them were laid (but not spiked) heavy planks of pine and hemlock, oak or walnut.
Built at a cost of about $2000 per mile, they were very profitable at first. There were toll gates at intervals of 5 or 6 miles. On the first stretch of the Southwestern Plank Road, the tolls were 12 1/2 cents (one "bit") for a man on horseback, two bits for a single team, and three bits for a 4- horse vehicle.
In September, 1848 the Southwestern Plank Road was completed from Chicago to Doty's Tavern at what is now the intersection of Ogden Ave with Joliet Ave. in Lyons, In 1850 it was extended to Brush Hill and Fullersburg (now Hinsdale), and in 1851 to Naperville. From there, a plank road was built to Oswego and Little Rock; and another to Warrenville, St. Charles, and Sycamore.
That was the first of a network of plank roads that radiated outward like the spokes of a wheel. Chicago was the hub. In 1849, the Northwestern Plank Road was constructed on Milwaukee Ave. to Oak Ridge at what is now Irving Park Blvd.; thence to Dutchman's Point (now Niles); and finally to Wheeling. The Western Plank Road was built westerly from Oak Ridge to Bloomingdale in DuPage County and thence to Elgin.
In 1851 the Southern Plank Road was constructed along the lines of State St. and Vincennes Ave. as far as Kyle's Tavern at about 83rd St. where it was halted by the approach of the Illinois Central RR. In 1854 the Blue Island Plank Road was completed on Western Ave. to its junction with Blue Island Ave., then the southwest corner of Chicago. There was also a 5-mile plank road parallel to the lake shore from North Ave. and Clark St. to Green Bay Road.
The planks soon warped, decayed, and frequently floated away or were "borrowed" by neighboring settlers. After a few years, with little or no maintenance, most plank roads became so uncomfortable and dangerous that they were abandoned. The decline of those "revolutionary improvements" was almost as rapid as their rise, replaced by gravel and brick roads, railroads, and street cars.
Much of the foregoing information was obtained from "Chicago's Highways -- Old and New", by Milo M. Quaife.