I’ve spent a good chunk of my eight years in Chicago chillin’ in 60614, but last week I was lured outside of its bounds for two adventures with only these directions in common: Take Lake Shore Drive south.

First up: The Horseshoe Casino in Hammond, Indiana—which, as far as I’m concerned, is the closest thing we have in the Chicago area to Disney World. Between concerts, media outings, grand-opening events, and random nights with friends, I’ve wound up there at least ten times since the $500-million renovation in 2008. I’m not much of a gambler—most of my bets are placed at racetracks and are based on the relative glamour of the jockeys’ outfits—so the allure of Horseshoe is, for me, more about the food (Jack Binion steak sampler, anyone?), the music (the Venue’s acoustics are impeccable), and, most of all, the people-watching. The best place to chat up fellow clientele is in one of the two casino-floor bars, Push and Vintage 51, and while I usually prefer Push for its clubbier vibe, on Tuesday night I found Vintage 51 to be populated with the more talkative drinkers. There, I spoke to Artie and Steve from Crete—the Indiana town, not the Mediterranean island—both happily sipping vodka cocktails and puffing away (smoking is still allowed in Hammond). “I’m what you’d call a regular,” said Artie, who admitted it took him a while to adjust to last year’s renovation. “I used to miss the old boat a lot, but this kind of grows on you.” He gestured toward the plush, Vegaslike surroundings. Speaking of Vegas, Steve added, “We’re much more profitable here than there.” Encouraged, I sat down with three friends at a quarter slot machine, where we took turns pulling the lever. We promptly won $90, then went home while we were ahead.

On Friday I found myself just a few miles—yet worlds away—from Hammond, in Hyde Park, where my friend Jenny, a University of Chicago alum, took me to her favorite college bar, the Woodlawn Tap (1172 E. 55th St.; 773-643-5516), widely known as Jimmy’s after its former owner. “Look at all the hot nerds! They’re everywhere!" a delighted Jenny exclaimed on our initial lap. The bar’s three rooms were comfortably abuzz with the intellectual chatter of sweater-clad U. of C. grad students. We found two barstools and ordered beers from the sweet-smiled, soft-spoken Matt, a full-time lawyer who has bartended weekends at Jimmy’s for 15 years, just because he likes it so much. With everything from Aerosmith to Beyoncé issuing from the bar’s speakers, Jenny and Matt launched into a discussion of favorite bands, and I corralled a group of Ph.D. candidates to ask what I thought was a good icebreaker for a bar full of readers and thinkers: What’s the last book you read? Answers ranged from theology texts to The Savage Mind, but one intense 20-something with dark hair down to his shoulders (“He’s peering at you,” Jenny had noted earlier. “You have a peerer”), was more interested in reading my palms. “You’re essentially very confused,” he reported, staring intently at my—um—hands. “You should go backpacking with me in the Himalayas next summer. I think you’d find it extremely enlightening.”

“I’ll give that some thought,” I told him. For the moment, just being on the other side of town was enlightening enough.