Start in England with the Roman town of Chester in Cheshire (blend of Chester+shire). There are many other Chesters as well as Eastchesters and Westchesters which are sometimes spelled as two words. There are also Portchesters. "Chess" appears in Dutchess County, New York, USA. This typically results in irrelevant returns when searching for chess.
Anyone think of a place around the world that has "chess", "ches" or similar in the name, I can think of...
Manchester
Chesterfield
Can someone come up with 25 more to shame me ?