The quest for an apartment is a perilous journey filled with pitfalls and double-talk, where that "Sunny Lake View 2BR" always turns out to be a windowless closet plopped between perpetually warring Canadian-American gangs. Arm yourself, with Rent Jungle
A just-launched repository of more than 15,000 listings within five miles of the Loop all organized in a sexy, easy-to-navigate map format, RJ is the brainchild of a Midwest duo that took their diverse experiences (one in the tech world, the other in real estate) and spawned the most logical hybrid of their abilities, considering their condo made from Apple IIC's totally froze.
The crazy-simple process starts with you entering the zip or address you're hoping to land and filtering by needs (price, bedrooms, bathrooms), after which, a Gmap pops up w/ listings culled from a variety of sites (Craigslist, Rent.com, etc) and pinpoints locations for each loaded w/ scrollable specs, so when they entice you with claims of a cemetery view, you can verify you won't be stuck overlooking the less desirable ad hoc wooden cross section.
Mo' benefits: their search engine refreshes every four hours, and gives you the option of a list format that links to a Google-powered Street View, unless your potential new property is managed by P.V. Hindenburg, LLC
If you're totally thirsting for more, there's also a hefty range of articles providing advice on various aspects of the apartment world, from roommate consideration to "13 things to consider before signing a lease", though alarmingly, there's no advice for what to do when you wake up with a warm moose head tucked neatly under your bedspread.