Rainbo in Chicago is awesome, we are lucky to have it. Definitely get either John or Jodi for fitting, in my experience they are good with appointments. Running behind sometimes maybe, but certainly taking care of customers with appointments first. They also have lots of used skates on consignment, if you are lucky to fit into them.
How long are you staying in Chicago? I'm slightly worried they may not have what you need in stock and multiple trips are normal. I wear stock Jackson and visited them a few times for adjustments alone. A friend of mine has narrow heels and certainly made it much harder.