Howdy fellow Chicagoan. My first foray into home espresso was a Gaggia Classic and a Baratza Encore. That was more than enough to replace my forays into the coffee shops.
A friend of mine uses a cheap breville and preground coffee and is satisfied, so I think it all depends on how picky you are.
Let me know if you have more specific questions as well. I've been making espresso at home for about 7 years now, so I've been through most of the growing pains.