AB & Ancient,
"Doesn't sound like a safe place to vacation................"
That's entirely untrue!!!!
There is so much to do and see here, not to mention one of the highest per capita taverns/pubs in the nation.
As with any large city there are certain places the you simply do not belong in. A vast majority of the City's South ( and to some degree portions of the West ) Sides are areas that make the news with all of this violence.
Chicago used to be -- and to some extent still is -- a city of neighborhoods with each having a distinct ethnic make up. Now it is more of a mismatch but still alot of fun to see and be in.
Even on the south side there are certain areas that are safe as anywhere on the planet. Some of the more popular places on the South Side are The Cell aka Comisky aka (White)Sox park, Chinatown, Bridgeview -- original home of Chicago's Mayor, the Mayors late father and all kinds of politcal types involved in all kinds of larceny and greed. the former Meigs Field, Soldgiers Field, Museum of Natural History -- Home of Sue the T-rex -- the Planatarium and the Aquarium are located on a the South End of Grant Park in a rather Large campus, situated right on/near Lake Michigan. The Midway area Neighborhood is interesting for a wide variety of resturants and bars -- blue collar workers are the bread and butter of this area.
Combine the above with Downtown Proper, GreekTown, Michigan Ave., Gold Coast/Rush Street areas, Lincoln & Wicker Parks -- Yuppie heavens -- Wrigley Field ( GO CUBS!!!! ) { if you find yourself in Chicago on a Cubs Game day get over to Wrigley Field (take the "EL" train there and either the El or a Cab back, there is NO PARKING for visitors in this area) and instead of going into Wrigley Field do a Pub Crawl -- there are at least a hundred taverns in the area -- and enjoy the game on the various taverns TVs, spend your money on beers not tickets
} and several other Neighborhoods both North and West make for one hell of a good time.
And do not forget about the Pizza joints that are just to numerous to list mention -- yes you can get that flat stuff that most of the rest of the world calls pizza, but why when you get a Deep Dish "Chicago Style" Pizza and have a meal rather than a snack.
Do a little lookup on things to do and you will see a Weekend is not anywhere near enough time to see and enjoy Chicago.
Sorry for the tourisim commercial but Chicago is one Hell of a place to see and Enjoy!!!!