Chicago Investors — Anyone Here Running Co-Living Successfully?

Chicago, Illinois
Innovative Strategies
9moFollow

Chicago Investors — Anyone Here Running Co-Living Successfully?

Miles Mac
Member since 2025 · 4 posts · 2 votes

Hey everyone, I’m Miles. I co-own and self-manage two multifamily buildings on the northwest side. Both are stabilized long-term holds. My business partner and I are now exploring ways to maximize cash flow in our next investment. 

The model that interests me most is co-living / renting by the room. I’ve seen it executed well in other markets and I’m curious how it translates to Chicago’s unique legal, zoning, and neighborhood landscape.

Is anyone here successfully running co-living in Chicago?

I'd love to get a high level understanding of what is leading to success with this model. Would also love to connect with anyone currently operating or interested in this space. 

Appreciate any insight or connection.

Cheers, 
Miles

1Reply
158 views

Most Popular Reply

Victor SoBusiness Member
Real Estate Agent · Chicago, IL · Member since 2017 · 325 posts · 193 votes
9mo
Quote from @Miles Mac:

Hey everyone, I’m Miles. I co-own and self-manage two multifamily buildings on the northwest side. Both are stabilized long-term holds. My business partner and I are now exploring ways to maximize cash flow in our next investment. 

The model that interests me most is co-living / renting by the room. I’ve seen it executed well in other markets and I’m curious how it translates to Chicago’s unique legal, zoning, and neighborhood landscape.

Is anyone here successfully running co-living in Chicago?

I'd love to get a high level understanding of what is leading to success with this model. Would also love to connect with anyone currently operating or interested in this space. 

Appreciate any insight or connection.

Cheers, 
Miles

Thanks for the mention @Aaron Zimmerman! @Miles Mac I own and manage 11 units (+ a couple non-conforming basement units) and  most of what I do is rent by room/ co-living stuff. I’m happy to answer any questions you may have! Feel free to reach out anytime! 

Victor So Real Estate LLC517 Reviews
WebsiteView Page
2Reply
See this reply in the discussion

9 Replies

Jump to latestLatest
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    9mo

    @Victor So does co living/rent by the room in Chicago. I'd recommend reaching out to him!

    [email protected]
    Brick House CPAs53 Reviews
    WebsiteView Page
    1Reply
  • Miles Mac
    OP
    Member since 2025 · 4 posts · 2 votes
    9mo

    Thanks Aaron!

    0Reply
  • Victor SoBusiness Member
    Real Estate Agent · Chicago, IL · Member since 2017 · 325 posts · 193 votes
    9mo
    Quote from @Miles Mac:

    Hey everyone, I’m Miles. I co-own and self-manage two multifamily buildings on the northwest side. Both are stabilized long-term holds. My business partner and I are now exploring ways to maximize cash flow in our next investment. 

    The model that interests me most is co-living / renting by the room. I’ve seen it executed well in other markets and I’m curious how it translates to Chicago’s unique legal, zoning, and neighborhood landscape.

    Is anyone here successfully running co-living in Chicago?

    I'd love to get a high level understanding of what is leading to success with this model. Would also love to connect with anyone currently operating or interested in this space. 

    Appreciate any insight or connection.

    Cheers, 
    Miles

    Thanks for the mention @Aaron Zimmerman! @Miles Mac I own and manage 11 units (+ a couple non-conforming basement units) and  most of what I do is rent by room/ co-living stuff. I’m happy to answer any questions you may have! Feel free to reach out anytime! 

    Victor So Real Estate LLC517 Reviews
    WebsiteView Page
    2Reply
    • Miles Mac
      OP
      Member since 2025 · 4 posts · 2 votes
      9mo
      Quote from @Victor So:
      Quote from @Miles Mac:

      Hey everyone, I’m Miles. I co-own and self-manage two multifamily buildings on the northwest side. Both are stabilized long-term holds. My business partner and I are now exploring ways to maximize cash flow in our next investment. 

      The model that interests me most is co-living / renting by the room. I’ve seen it executed well in other markets and I’m curious how it translates to Chicago’s unique legal, zoning, and neighborhood landscape.

      Is anyone here successfully running co-living in Chicago?

      I'd love to get a high level understanding of what is leading to success with this model. Would also love to connect with anyone currently operating or interested in this space. 

      Appreciate any insight or connection.

      Cheers, 
      Miles

      Thanks for the mention @Aaron Zimmerman! @Miles Mac I own and manage 11 units (+ a couple non-conforming basement units) and  most of what I do is rent by room/ co-living stuff. I’m happy to answer any questions you may have! Feel free to reach out anytime! 


       Hi Victor. Thanks for the response. Would love to dive in deeper here. Going to shoot you a text to connect! 

      0Reply
  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    9mo

    What's up @Miles Mac!  You've got a great resource with Victor.  I've got a couple other connections who mess with it.  Another website for listings and likely other good knowledge is bungalow - they were the original rent by the room platform.

    If you haven't been out to any of the local Chicago meetups definitely make some time.  You can for sure network in person with some investors who are renting by the room. https://www.biggerpockets.com/forums/521-real-estate-events-...

    Ultimately, it's a lot more work with a much greater potential for issues.  Personally, the only reason I'd recommend it is if you were going to go all in and make that your sole strategy - Systems and process will be VERY key...or just keep buying long-term holds.

    [email protected]
    Quality Builders4.966 Reviews
    WebsiteView Page
    2Reply
    • Miles Mac
      OP
      Member since 2025 · 4 posts · 2 votes
      9mo
      Quote from @Jonathan Klemm:

      What's up @Miles Mac!  You've got a great resource with Victor.  I've got a couple other connections who mess with it.  Another website for listings and likely other good knowledge is bungalow - they were the original rent by the room platform.

      If you haven't been out to any of the local Chicago meetups definitely make some time.  You can for sure network in person with some investors who are renting by the room. https://www.biggerpockets.com/forums/521-real-estate-events-...

      Ultimately, it's a lot more work with a much greater potential for issues.  Personally, the only reason I'd recommend it is if you were going to go all in and make that your sole strategy - Systems and process will be VERY key...or just keep buying long-term holds.


      What's up Jonathan! You probably don't recognize me but I've been to your Cashflow Breakfast Club a couple times. I've made some great connections there and definitely need to start coming back.

      When you say much greater potential for issues what comes to mind? Legal? Mainly  Operational? Exit Risk? 

      Chicago CashFlow Breakfast Club
      1Reply
  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    9mo

    I have had two clients do it, as @Jonathan Klemm mentioned it can be more issues. One did it themselves and said was profitable over LTR but way too time consuming managing so they switched it back to LTR. The other subleases to a company that does co living which pays slightly over market lease rate and been there a few years now. They provide all the furnishings and handle all the operational management so easier then doing it yourself. The company is called June Homes.

    2Reply
  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    9mo

    My fault @Miles Mac - We've had a couple of people pass through the Chicago Cashflow Breakfast Club since you...either way you've got a good looking picture so I should recognize you lol

    Risks mainly lie in the time commitment required to manage &lease, and in the actual management of the people within the property.  VERY CLEAR EXPECTATIONS and Rigours vetting requirments have to be in place.

    I'm not worried about the legal or exit risk - it's really just the people and the time.

    [email protected]
    Quality Builders4.966 Reviews
    WebsiteView Page
    0Reply
  • Robert J. Rhodes
    Investor · Houston · Member since 2022 · 56 posts · 27 votes
    6mo

    I have to echo @Jonathan Klemm here. It’s very systems and process driven.

    I’ve been operating a shared housing property for several years, and what I’ve found is that the difference between something that performs well and something that becomes management heavy usually comes down to a few underlying variables.

    The property itself, the location within the city, and how the day-to-day operations are structured tend to matter more than the high-level concept.

    The model can work well, but it’s much more sensitive to those inputs than most people expect going in.

    Curious how others here have seen that play out in Chicago specifically.

    Robert J. Rhodes

    1Reply
Join the conversationCreate a free account to reply, vote on answers and follow this thread.
Log InJoin for Free