I have a friend in Chicago who’s re-entering the biking world after a layoff of several years. I think she’ll probably end up buying a hybrid, maybe a low-to-mid-range road bike. What stores in Chicago will give her an expert fit, but don’t necessarily specialize in high-end bikes?
Village Cycle has a ton of low to mid range bikes, but don’t expect an expert fit. Their advertising hook is that they’ll get you on a new bike and out of the shop in an hour.