Hi--I've dealt with 2 family owned jewelers over the years, as well as with Jewelers Row.
Sandberg Jewelers is run by 2 sisters who took over from their parents; they're located in the Village Crossing mall (Central/Touhy in Skokie); kitty corner west of Barnes and Noble. Prior to that they were at Six Corners since the 1900's. Sandberg has repaired my heirloom diamond ring, and my husband has purchased many stunning estate (previously owned) pieces from them. My husband now has a vintage pocket watch collection mostly purchased there.
Schierer & Popp Jewelers (3912 N. Cicero, Chicago) specializes in watch repair, and does other jewelry repair as well. Donna the owner shows me her constantly changing stash of costume and fine jewelry several times a year. I bought a beautiful 1950's diamond & platinum eternity band from them last Christmas at less than 1/2 of retail. Previously owned is previously loved--good karma. Both jewelers do appraisals.
I've browsed through Jewelers Row, and we bought my estate diamond ring from one of the platinum specialists, name no longer remembered. It's a good place to check out what's available and to compare the price points. Most people are very helpful. Happy shopping! Anna