How I Got a Good Deal on a 2-br in a River North High-Rise

Months Free Mike crushed his search for a 2br apartment for his girlfriend and himself and was rewarded with a good deal on a brand new 2br unit in a River North high-rise. He quickly learned where to find value in the Chicago apartment market and how to effectively use Chicago’s brokerage intermediaries.

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How I found a 1br high-rise apt in Gold Coast

Nancy Negotiator (young professional working downtown) did a killer job finding a 1-br apartment in a Gold Coast high-rise. Most interesting about her process is that she negotiated with her landlord for a full kitchen renovation (cabinets, counter tops, and appliances) prior to her move-in at a low additional rent cost. Here’s how she thought about and executed her search process:

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How I found an apartment in Old Town

I started looking for an apartment in mid-May with a goal of moving in on July 1. In hindsight I should have started in early April because doing so would have allowed me more time to get a feel for the market before the bulk of the July 1 inventory became available.

Why I wish I had started my search earlier than I did

While the bulk of July 1 inventory seemed to post to sites like Craigslist, Zillow, and Domu in mid-May, I wish I had begun my search a month earlier so as to develop a sense of fair market value before I started seeing places I could potentially rent. It takes time to get a feel for what’s a decent deal and what’s not, and you really want to be able to walk in and say yes immediately when a good deal comes along for your desired lease start date.

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Loop – 151 North Michigan Avenue – 37th floor


How likely would you be to recommend your apartment to a friend? (1-10)


Most surprising things about this apartment

During 2016 and 2017 a troop of musicians known as the “bucket boys” banged buckets with sticks on Michigan Ave directly across the street. The bucket boys seemed to know something about acoustics because they chose to play immediately in front of a building with a concave shape that caused the sound of their banging to reverberate up and down Michigan.

The bucket boys showed unbelievable physical stamina in that they played from late morning til night seemingly without rest. They also proved resistant to police – Whenever residents of our building called in a noise complaint, the bucket boys would momentarily relocate once the police arrived but would be back at full strength within 20 minutes.

I’m not sure what happened to them, but they seem to be quieter this year.


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