Hello - Looking to Acquire and Operate Co-Living House Hack near Chicago, IL

Hello - Looking to Acquire and Operate Co-Living House Hack near Chicago, IL

Investor · Chicagoland, IL · Member since 2025 · 3 posts · 3 votes

Hi!

I am currently based in Oakland, CA but am planning a move to the near north and west suburbs of Chicago, IL in 6–12 months. I am working to acquire and operate a co-living house hack modeled after those run by Miller McSwain, Sam Wegert, and Grant Shipman. Even more specifically, I want to acquire a property with two separate buildings (e.g. SFH + SFH or SFH + ADU / coach house), live in one with my family of four, and operate the other as a co-living house. My wife and I are getting involved in real estate after a decade or more of pursuing financial independence using non-real-estate strategies, primarily investing in index funds. I'm a recovering academic, and leaving that field has finally opened up some bandwidth to explore real estate. House hacking seems like a powerful way to offset housing costs, and co-living seems like a viable strategy for improving cash flow.

I'm joining BiggerPockets to connect with people who are a few steps ahead of me, learn what I can, and contribute to the community. On that note:

- I'd love to connect with anyone who is operating a residential-scale co-living property (bonus if it's in the Midwest and double bonus if it's in Chicagoland!) or otherwise connected to the co-living world.

- Based on what I've seen so far, the kind of property I'm looking for is rare, which is one reason I'm not expecting to close until the end of this year or early next year. If you happen to know of something that might fit, please don't hesitate to reach out!

- I'd appreciate a discussion about whether combining house hacking, co-living, and an ADU in this way could work in the Chicago suburbs, and if so, how you see it working.

Looking forward to connecting,

Josh

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    Real Estate Broker · 3412 S. Harlem Avenue Riverside, IL 60546 · Member since 2015 · 6k+ posts · 5k+ votes
    1y

    @Joshua Rule welcome to the forums! Where in the western suburbs are you looking to purchase? There are definitely coach houses in some of the urban core suburbs like Oak Park, Forest Park, etc. Are you hoping to live in the coach house and operate the main house as a coach house? 

    Your strategy is possible for sure. I would say these properties are few and far between, but not exactly rare. I have sold a handful of them, and even recently sold an older 2 flat in Oak Park that had a 5-bedroom coach house. They exist for sure!

    See this reply in the discussion

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    • Aaron ZimmermanBusiness Member
      Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
      1y

      Welcome@Joshua Rule! I hope you have good luck with finding your property! 

    • Real Estate Broker · 3412 S. Harlem Avenue Riverside, IL 60546 · Member since 2015 · 6k+ posts · 5k+ votes
      1y

      @Joshua Rule welcome to the forums! Where in the western suburbs are you looking to purchase? There are definitely coach houses in some of the urban core suburbs like Oak Park, Forest Park, etc. Are you hoping to live in the coach house and operate the main house as a coach house? 

      Your strategy is possible for sure. I would say these properties are few and far between, but not exactly rare. I have sold a handful of them, and even recently sold an older 2 flat in Oak Park that had a 5-bedroom coach house. They exist for sure!

    • Investor · Chicagoland, IL · Member since 2025 · 3 posts · 3 votes
      1y

      Thanks, @John Warren! Yes, on the west side we're looking in Oak Park and Forest Park. The plan would be, as you suggest, to live in the coach house and operate the main house as a co-living space. 

      We've seen a couple of these properties that look like they might work well, but are definitely still on the hunt. Thanks for your encouragement!

    • Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
      1y

      Hey—love the intentionality behind your plan and the clarity of your vision. Co-living as a model is still underutilized in Chicagoland, especially in the near north and west suburbs, but the demand for affordable, flexible housing definitely exists—particularly near job centers, transit lines, and medical or university anchors.

      You're absolutely right that finding a setup with two separate structures (SFH + coach house/ADU or legal nonconforming layout) is tough—but not impossible. I've helped a few people explore similar strategies here and would be happy to share what I've seen work in places like Berwyn, Cicero, Oak Park, and certain pockets of Evanston and Forest Park. Zoning and occupancy regs vary a lot by suburb, so navigating local nuance becomes key—especially if you’re trying to avoid running into issues with shared housing regulations.

      Really excited for you and your family—it sounds like this next chapter could be both financially powerful and values-aligned. If you ever want to connect offline or compare notes, I’d be glad to chat. Always happy to help fellow FI-minded folks map out creative living and investing strategies!

      Looking forward to seeing your journey unfold.

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