House-Hacking in Chicago

[Matt Byrne]

Hey everyone,

I’m in the process of getting my first real-estate deal planned out, and have decided that a house-hack makes the most sense. I’ve heard time and time again that it’s a great way to get introduced to the business, and it will work well for my current way of life. Part of finding the right deal, from my understanding, is choosing a market, learning as much as possible about that market, and making connections and getting out there to find the properties. My business partner and I have been analyzing different areas in Chicago, and we are not quite sure where we want to invest - the city or the suburbs. Cash-flow is the top priority; appreciation would be nice. There are cases for both locations, so I am wondering if any of you have experience house-hacking in Chicago (or the suburbs) or investing in multi-family units in these areas. Are there areas you have had particular success in? Areas you would avoid (that otherwise would be considered 'fine' or 'safe' neighborhoods by non-investors)? Would you avoid investing in Chicago all together? I would love to hear any insights, and always appreciate your sharing of your knowledge.

[Tom Shallcross]

Hi @Matt Byrne and welcome to the site. Househacking on the North and NW side of the city is extremely popular, you just need to have realistic expectations as it is very competitive. It's a great strategy, but it's not going to be a big cashflow producer for you regardless of where you invest. 

We had @Brie Schmidt on our Podcast (episode 5) and you can reach out to her to talk through the Northside neighborhoods.

@Jake Fugman is anther investor-friendly agent that can talk about different areas of the city as well (Northside and the Pilsen, little village area)

@John Warren can help you in the inner-Western burbs - Berwyn, Cicero...etc