Should I renew my Non-Immigrant Type O-A Retirement Visa in Thailand or apply for a new one in Chicago?

@Bruce ********

, what I would do IS;

Just prior to August 22nd, exit/re-enter the country. That will get you stamped in until the end of august 2019. Then before you leave the country buy a re-entry permit so that when you do come back you will be stamped in until the end of August 2019.

To give you any answer we'd need to know what is the "Enter Before" date on the visa?

Depends on your "enter before" date and how long you expect before your next visit to Thailand... If "enter before" date is in near future still and you can do "border bounce" within (and as close as possible) that "enter before" date, you will be stamped in another whole year. Then you get a re-entry permit before leaving to the US to keep your new admitted to stay 'alive'. If this works for you, you would gain roughly one more year to think about your next step...

You can not renew the visa, but you can apply for the 1 year of Extension of Stay. As you write you plan to return to Thailand at some undetermined date in the future I would say, apply for a new Non Immigrant O-A visa before you make your way back into Thailand.