Here's my .02 cents. I've ranked these by the number of successful experiences with providers who I first contacted through advertisements on that site. Also, the least amount of fakes, scams or well below average sessions. These are also from the perspective of in the U.S. and Chicago. There's many more sites outside of the country that work for various other countries and areas:
Top sites:
1. Eros - https://trans.eros.com/illinois/chicago/sections/chicago_trans_escorts.htm
2. TS4Rent - https://ts4rent.eu/shemale-escorts/chicago/
Tied for 3rd. TS Escorts - https://www.tsescorts.com/illinois/chicago/shemale-escorts
Tied for 3rd. Hot - https://hot.com/us/il/chicago/shemale-escorts/gallery
5. Sumosearch - https://sumosear.ch/images/tags/chicago-il/trans-shemale-escorts
6. Tryst - https://tryst.link/us/escorts/illinois/chicago/categories/trans
More questionable sites:
7. TS Masseur - https://tsmasseur.com/ts-massage/chicago/
8. T-Escorts.com - https://chicago.t-escorts.com/transgender-escorts
9. List Crawler - https://transx.com.listcrawler.eu/brief/escorts/usa/illinois/chicago/1
10. Adult Search - https://adultsearch.com/us/illinois/chicago/tstv-shemale-escorts
11. Skip The Games - https://skipthegames.com/posts/chicago/ts-escorts
Sites best for other countries not U.S.:
12. D.Net - https://distintas.net/usa-illinois-chicago
13. Shemale wiki - https://www.shemalewiki.com/?id=859&cityid=126&lan=en
What are other peoples thou8ghts/experiences?