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Apartment Hunting in Chicago

How to avoid pitfalls and snag your Windy City hideout


We're lucky here in the Second City. We're situated within a dense and enormous cultural hub, full of music and nightlife and art, and yet we don't face the exorbitant costs of living that plague most major cities. New York used to be packed to the brim with starving artists and musicians, but now Manhattan only accomodates the wealthy (or the offspring of the wealthy). Former sites of cultural revolution have been paved over with boutiques and five-star restaurants. Chicago's not without its yuppies, but at least you don't have to have a yuppie-sized income to live here. 
I just went through the motions of moving between Chicago neighborhoods. I'm leaving my stagnant university bubble and launching upwards into the real world. The process of locating and securing an apartment wasn't without its bumps, though. There are many channels through which you can search for your perfect apartment, but some are more useful than others. After going through the apartment hunting process twice, I know pretty well what sucks about searching and what works. Hopefully what I've learned will apply to those going through the same hoops. 
There are a good number of apartment listing directories available for free online. Some landlords and rental companies may still be putting out ads in the paper, but in general your most accurate and up-to-date information will come by you digitally. Craigslist is a huge resource that's constantly buzzing with new listings, but there's little quality control and few options for advanced searching. However, you're more likely to find landlords listing empty apartments themselves on Craigslist. An attentive landlord is the best person to get in contact with regarding a unit. They'll be more knowledgable about the apartment and building than a real estate agent, and they'll tend not to hassle you with sales pitches and schtick. You want to hear it straight, and you won't always get to from a company whose job it is to secure applications. Companies like Chicago Apartment Finders or Rent Smart Chicago will have decent listings  on their website, but you'll have to go through them to see the apartment and put in an application to live there. This process might be useful if you'd like to talk to an agent about narrowing down your apartment choices, but if you've already got a good handle on finding what you want, it'll generally just slow you down. I went to Chicago Apartment Finders and had a pretty bad experience when the agent assumed I had no idea what I wanted in an apartment and proceeded to lecture me about my options for way too long. I prefer the direct route of meeting a landlord or agent at the building, touring the unit, asking a few questions, and getting out within 20 minutes. Companies who turn a profit for every application they secure will tend to want to take up way too much of your time to keep you talking. 
Another site that's been advertised all over the city is It's a nice compromise between a site like Craigslist and a service like Apartment Finders. They allow landlords to post listings directly instead of going through a single company, but they also feature high-quality photos and an excellent search function. The site's not updated quite as often as Craigslist, but then again, it doesn't allow a constant influx of spam. It might be your best bet if you don't feel like filtering out all the bad listings that Craigslist is polluted with. 
Be wary of buzz words designed to mask or distract from undesirable qualities in an apartment. "Cozy" usually means "suffocating". Make sure you know how much square footage you're looking at before going in to a viewing if you're worried about space. "Sunny" apartments might also be unbearably hot in the summer if there's no air conditioning. "Charming" is a loaded word. Make sure it doesn't mean "dilapitated". There's a fine line between quirk and decay. 
A lot of Chicago landlords and rental companies are doing gut rehabs on old buildings now. The finished products usually include stainless steel appliances and granite countertops--excess amenities that can be used to inflate the price of an otherwise average apartment. Don't let yourself pay hundreds of dollars extra per month just because your counters are made of stone and not Formica. It may look nicer, but there's functionally little difference. New appliances aren't always significantly better than old appliances, either. Good kitchenware will last a long time, so don't restrict your searches to newly remodeled kitchens unless you really have to be the first person to cook in your place. It's more important to find a well-kept apartment than a new one--it's proof that the landlord actually cares about the long-term state of the place. 
As for landlords, you're far better off knowing them personally than setting up camp under the wing of a huge company. I lived with a certain student apartment monopoly for the past two years, and they could not care less when things went wrong with our place. They own so many buildings they start to lose track, and they certainly don't give a damn about their individual tenants. If you can, find an apartment in a building that's owned by just one or two people and establish a relationship with them. Make sure they care about their landlord job and are reliable about repairs and upkeep. If they own multiple buildings, make sure they're well acquainted with the particulars of each one. You don't want to be just another job in a long list--you want to make sure they are invested in your experience as a tenant in their building. 
Most importantly, be thorough and trust your gut. Research your neighborhoods and figure out which ones best suit you--Chicago's a huge place and different parts of it can feel like different cities. Gather up lots of listings. Call lots of agents and landlords and look at lots of apartments. If something feels off about the neighborhood, building, or unit, don't go further with it. You don't want to discover that your intuition was right all along three months down the line. When you do get down to brass tacks, be wary of excessive fees. Get copies of all paperwork. Beware that move-in fees are generally nonrefundable, while security deposits you get back. Never pay anything but an application fee before signing your lease--odds are, you'll be out both a deposit and an apartment. Scammers gonna scam. Be careful out there. 
Have patience with the process--finding a good apartment takes time, but it's worth it to have a habitable environment for the next year of your life. Chicago's a great city, and finding your perfect niche in it is worth the effort.