Looking to break into real estate in Chicago

6 Replies

Hey Everyone,

I apologize in advance for the longer post.. I have been a member here for a little over a year now, but this is my first time posting. I am 25 years old, and I have spent the past couple of years reading/listening to everything I can get my hands on regarding real estate investing, and my day job is in finance so I am pretty comfortable with the pro-forma aspect of things. 

I have finally saved up enough money for my first purchase, and I am looking for a fix and flip somewhere in the chicagoland area (I currently live on the west side, so I am most familiar with opportunities in neighborhoods like Logan Square, Wicker Park/Bucktown, Hermosa, Avondale, etc., but I am also considering up and coming neighborhoods on the south side like Woodlawn and Bronzeville). 

I am definitely in the analysis-paralysis stage, as it seems daunting to just jump right into something like this alone (any time I see a potential deal I get caught up thinking, "what am i missing, why hasn't anyone else jumped on this?"), so I am curious--what events/associations are best to join in this area so that I can expand my network and find a potential partner or even a mentor? Should I just start reaching out to agents/wholesalers? any thoughts anyone has would be much appreciated, even if it is just words of encouragement from someone who recently overcame this position!!


I am active in/around Naperville area. There is a couple of opportunities I can share, PM if interested.

I do also heavily working on for short-term rental which is very promising for cash flow. 

@Rob Munnings

If your only looking to purchase in the city I know a few great realtors that have a knack for finding good deals on the Up and Coming SW side neighborhoods like you talked about. And a few that work on the North Side as well. 

Send me a PM if your looking to work with on market leads 

or just send me a text my cell is in signature 

Saw your title and had a little laugh. My first thought was you could use a crow bar to break into real estate.

Best of luck and welcome to BP.

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