I’ve had all my alterations done by Paul Chang Custom Tailors in the Loop on the corner of LaSalle and Lake inside the Accenture building. I’ve been going to see Paul for the past 4-5 years.
One of the things I always stress to people who want to visit a tailor is to learn how to communicate exactly what you want. Bring photos, if you must. Open up and talk with them about how you like things — but listen to their feedback (if they don’t offer it, ask). Tailors aren’t mindreaders. They’re skilled at executing, but you have to provide the instructions. So, keep that in mind.
(This reminds me I need to do a FAQ section as this keeps coming up!)