Don't let 'em scare you 88. There's only a few small pockets of unsavory neighborhoods south of Madison. Just avoid everything East of the Ryan, most everything between the Ryan and Cicero from North Av. to 95th. South of 95th, stay west of Western. You'll do fine.
Problem is if you want the best pizza in the city you'll need to get to Crestwood. The best BBQ's also south. And of course if you golf, you should check out the Palos courses.
Oh and there's only 2 or 3 places for respectable seafood. Trust me, don't waste your time.
And don't let those "beaches" fool you. They look normal but they're not. Water's cold and the sand's like pea gravel.
But it is festival season and the mid-west really wakes up during the summer. The weather's perfect (or close) for being outside all day.
Oh yeah, buy the heaviest coat you can afford.....now.