When purchasing a condo, one has to take into considering how much they will be paying in homeowners association fees (or HOA dues), and the amount can range anywhere from a couple hundred bucks to well over $10,000 per month. The city's priciest condos cost millions of dollars, but the owners of these pads will continue paying thousands of dollars per month in HOA dues. Take for instance the big boss penthouse in the Trump Tower — asking $32 million plus an additional $13,244 per month in dues. Just a few months in association dues is higher than the salary of many recent college grads. However, one thing the list does reveal is that one can expect to have a steep HOA dues when living in vintage buildings along Lake Shore Drive, particularly co-ops.

Homeowners association fees generally cover things like exterior maintenance, building insurance, garbage pickup and so forth, however not all homeowners associations are created equal. Broker Christopher Mundy of @properties tells us:

HOAs vary from building to building and cover such items as services rendered, including heat, water, trash, scavenger-trash, on-site maintenance (building engineer), doorman, pool, fitness centers, major mechanical systems (elevator, boilers, ac compressors) on larger buildings, and most importantly a reserve allocation. The reserve fund for any building is an emergency fund used for any unforeseen issues that may arise; the objective of this fund is to protect the owners and provide a cushion versus special assessments against the owners. Older buildings (particularly those along Lake Shore Drive) have higher assessments due to ongoing maintenance. Co-op assessments are traditionally higher and usually include the property tax; for this reason the building attracts a unique buyer with the financial ability to pay a mortgage, on top of a $1000 plus HOA. When purchasing a unit in a housing cooperative, one is essentially buying shares of a building, not necessarily the ownership of a particular unit (although they're listed that way). And HOA dues can be quite high in co-ops due to this. According to Redfin agent Brian Cargerman,

When you buy into a co-op, your HOA dues include property taxes. Generally, this will raise your HOA dues over those of a traditional condo of a comparable size and quality. Additionally, in Chicago co-op buildings tend to be older, which means more maintenance – and higher dues to pay for it. So there you have it. Let's take a look at the map now, shall we?