Welcome back to Chicago! I'm in my late 20s and often dine in large groups with friends (all with varying paychecks...some students, some professionals and everything in between). While it would be helpful to know some more of your preferences (i.e. cusine, price point, quiet v. convivial, upscale or not, etc), I would recommend Quartino for a group. It's small plates Italian. While its nothing completely earth shattering, its fun for a group and certainly tasty. Those more inclined to label themselves "foodies" won't gag, but the less adventuresome diners won't be turned off either. You can order wine by the carafe. I've been there with both my girlfriends (nibblers) and my boyfriend (a big-ish eater) and both were happy with their experience Its also a fun atmosphere. It's located near a plethora of transportation options - the red line, the #22, #36, #156, the Michigan Ave busses - and there is an outdoor dining area out on State. I hope this helps and if you weren't looking for Italian or this price point, let us know and I'm sure there's tons of more options.
Quartino
626 N. State Street
Chicago, IL
312-698-5000
www.quartinochicago.com