It's a growth sector! By which we mean, outfits that help you discover the food of our city (and maybe meet other people in the process). Two came across our desk recently: Dishcrawl specializes in, well, dish crawls, that is, they set up an itinerary where you get to try out different restaurants in a neighborhood; they set it all up for a flat cost which gets you a welcome from the staff and a taste of the menu at each stop. It's a good-sized crowd— they say anywhere from 20 to 100 people— so that makes for a good number of chances to meet somebody and enough people that you can tailor your experience to your own degree of schmoozability with restaurant staff and chefs, we guess. Go here to learn more about upcoming events, which happen in a pretty long list of cities by now; there's a Wicker Park one on November 7 and a Loop one on November 13 coming up.
Sidetour, which started in New York and recently expanded to Chicago, offers a bit more unique experiences, not all about food but all of them small-group gatherings hosted by someone interesting— a chef, an author, a chocolatier— who cooks a dinner, or takes you on a tour, or shows you how to mix classic cocktails, or something. They have a dozen upcoming events, all interesting and unusual, which you can check out here.