If you end up in Chicago go to Great Lakes Tattoo. Currently you could get tattooed by Nick Colella, Mario Desa, Mike Dalton, Erik Gillespie, Frank William, or Matt "Beatdown" Ziolko. That's six killer tattooers right there. Not to mention, it's one of the coolest shops I've ever been in. Check out their work on Instagram. If you have to wait a bit to save up for the trip, it will be well worth it. Good luck with your hunt for great tattoos. This forum is a great resource. And if you ever get a chance to cross the border, come visit The Pearl in Toronto.