[4][5] Chesbrough's father was originally a farmer in Massachusetts, but he pursued other means of business, which mostly failed.

Chesbrough moved to Pennsylvania in 1830 to become a surveyor for the Allegheny Portage Railroad under the command of Colonel Stephen Harriman Long.

After he returned to his profession, Chesbrough became the engineer for the water systems of Boston, and helped to build the Cochituate Aqueduct.

The legislature of Illinois created the Board of Sewerage Commissioners on February 14, 1855, leading to the appointment of Assistant health officers to aid the cleanup, and by August the Council resolved to build a sewage system.

Chesbrough was appointed engineer of the Board of Sewerage Commissioners because of his work on Boston’s water distribution system.

In the late 1860s, the Illinois and Michigan Canal was dredged and deepened to expand its ability to handle the city's sewage and move it away from the lake, but continued population growth quickly outstripped the canal's waste management capacity.