The South Side gets a reputation as being one undifferentiated slum, but, as mentioned elsewhere, you have good neighborhoods and bad ones. I’ll try to share the wisdom I’ve gained as a longtime south side resident. But if you don’t believe me, you can check for yourself using the CPD’s crime-mapping tools (http://gis.chicagopolice.org/).
The South Loop (Near South Side) has changed very dramatically in the last decade. It’s as safe as Lincoln Park, I’d say. To the south, Douglas isn’t bad to about 31st Street, but clumsy urban renewal projects from the '60s left very little retail along the streets, which means there’s no street life, which means that you’re a little more likely to be a victim on the street than elsewhere. South of 31st, things get sketchier.
Bridgeport is perfectly fine. McKinley Park and Canaryville (part of the New City community area) look worse than they really are. Armour Square (what’s left of it - most of the neighborhood was demolished to build the Dan Ryan and the US Cellular Field parking lot) and Chinatown are pretty safe.
Grand Boulevard is rough, though the stretch along King Drive is very pretty. Oakland is too depopulated to be good or bad. Back of the Yards (the rest of New City) was never a good area.
Hyde Park, where I live, is very nice. The University of Chicago circled the wagons about 40-50 years ago and saved the neighborhood from a spiral of decay through its own private police force, incentives to get faculty and staff to live in the area, and aggressive (and controversial, and not always smart) urban renewal. I have no problem walking alone through Hyde Park at night. South Kenwood is the same; north Kenwood isn’t great but it’s getting there.
(Incidentally, I had a friend who absolutely refused to visit me in Hyde Park because she thought it was too “ghetto.” I checked the CPD database, and it turned out that her supposedly safer street in Ukrainian Village had double the crime of almost anywhere in Hyde Park.)
Woodlawn has come back from the brink, but it has a ways to go. The areas not patrolled by the U of C Police are not good. Washington Park is bad; I’m hoping that the Olympics will inspire/shame the city into doing something about that. Englewood is the worst place on south side, IMO, but you’re unlikely to be a victim of crime merely driving down 55th/Garfield.
South Shore looks nicer than it really is, which is shame, because it looks really nice; the neighborhood changed from almost entirely white to entirely black between 1960 and 1970 without the strife and disinvestment that accompanied that process in many other neighborhoods at the time. I have no problem walking around the area near Jackson Park during the day, but I’d be more circumspect at night.
Grand Crossing? Forget about it.
Chatham is hit or miss. Parts are quite nice, but the western half goes downhill pretty quickly. Here the city gets more middle-class and a bit suburban, and so the crime rate tapers off a bit. Calumet Heights is a little nicer still. South Chicago (the neighborhood) is worse, much worse, but the stretch along the lake is nice.
Roseland and West Pullman are very rough, but Pullman itself is like a little oasis of safety. It’s a little gritty, though, but there’s some talk that the (now vacant) Pullman headquarters building might someday serve as Obama’s presidential library, which might cause the rest of the neighborhood to have some grit sandblasted off.
Mt. Greenwood is okay, from my understanding, and Beverly is very safe. Washington Heights is a smidge better than Roseland, but not by much.
I’ve never been to Hegewisch (it’s on my list), but my understanding is that it’s pretty safe. East Side is less so, but it could be worse.
In conclusion: worse than the North Side, not as bad as the West Side, but it really depends on the neighborhood. Don’t fear Hyde Park or Bridgeport, stay the hell away from Grand Crossing and Englewood.
P.S. Everywhere I’ve gone, I feel pretty safe in my car, especially during the day; carjackings are pretty rare here.
