House Hacking Chicago Multi-Unit Properties in 2025

[Andrew Burrell]

Hi everyone,

My name is Andrew and I am currently located in Boston, MA. My girlfriend and I are looking to move to Chicago some time in 2025 (likely the fall) for her job, and we are looking to buy a small multifamily property (2-4 units). We will live in one of the units and rent out the other(s).

I became extremely interested in real estate investing in 2023, and with the help of my dad I actually purchased an out of state single-family investment property in Northwest Arkansas that is set to close in a couple weeks. I have already secured renters and am very excited to get started.

Regarding the Chicago market, I have come to understand that there is an abundance of multi-family properties, but it is important to note the property taxes outside the city limits can be very high. It is also obviously important to make sure the property is located in a good neighborhood.

I am still over a year away from buying a property in Chicago, but I wanted to post here to get to know some people in the market and hear any advice/thoughts any people on here may have. While I do currently have one investment property, this will be my first house hack, so I am very excited to learn any tips and tricks to look out for in this particular market.

Looking forward to hearing from you guys!

Andrew

[Jake Fugman]

@Andrew Burrell congrats on the first purchase!  House hacking is an awesome way to leverage a low down payment to build your multifamily portfolio.  

I would recommend first establishing what your financing options are based on your cash on hand and cashflow expectations.... 5% down? Conventional? FHA? etc. Then speak with several investor friendly brokers in the area to gather feedback on what the cashflow #s look like with those options. Ex: Can I break even post move out with 5% down in X areas with X budget? There is a "Find an agent" tool on BP that will connect you to agents that act as solid resources to get started.

I also recommend the "Straight up Chicago Investor" podcast that @Tom Shallcross and @Mark Ainley host.