Looking for Strategies: Chicago 3–4 Unit House Hack With Today’s Rates

Looking for Strategies: Chicago 3–4 Unit House Hack With Today’s Rates

Member since 2025 · 14 posts · 8 votes

My goal is to purchase a 3–4 unit property in a B-class neighborhood in Chicago and house hack. Ideally, I’d like to focus on areas such as Logan Square, Bucktown, or Avondale. The challenge I’m facing is that with current interest rates and only 5% down, it’s been very difficult to find a property in the $800K–$900K range that even breaks even, let alone generates positive cash flow.

I’m concerned that by going with a higher purchase price, I’ll be locking myself into a deal that won’t cash flow for years. For those with experience in Chicago’s multifamily market, what strategies or alternative approaches would you suggest? Should I be broadening my search to other B-class neighborhoods like Pilsen, Ukrainian Village, or Irving Park that might offer better numbers while still providing strong long-term potential?

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

@Rochelle Fernando you are correct that the delta isn't what it was three to five years ago. Most house hacks are more of a break-even situation when you find a "good" one, and you are mostly looking at the longer-term benefits of real estate like appreciation, depreciation and debt pay down. The main thing to remember is that real estate has always been a get wealthily slowly game. I think anyone who might move out of the area in a few years should not be looking as much at house hacking. If someone is from the Chicago area and has roots, it often times makes sense to buy a good building in an area you like versus renting. 

The neighborhoods you referenced are all great spots. The rents have been absolutely on fire the past few years. We own in Avondale and manage in Logan Square, and the rental increases have been fantastic. That NW side is such a good, long-term area to own in. 

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  • Tj FlorosPro Member
    Real Estate Agent · Chicago · Member since 2025 · 95 posts · 74 votes
    1y

    Hi Rochelle,

    I think you can definitely find deals that break even on the MLS and some do cash flow, post house hack! Just need to underwrite the deals correctly. When I'm working with clients my goal is always to get them into a 2-4 unit where they can live below market rent while house hacking, and once they move out the building should cash flow. Now with the rates as high as they are now these deals don't come around very often, but when they do they move fast which means you have to move fast. If a good deal goes on the MLS on Wednesday night by Friday/Saturday it's probably going under contract, some even faster within 24 hours. Every week I run the numbers on deals that are new on the MLS for that week and send the best ones to my clients. I just toured a cash flowing turn key3 flat in Logan Square a couple of days ago with a client. Although it was not a perfect for them even at 5% it would cash flow a couple hundred bucks a month post house hack.

    I think you have the right mindset to find properties where the numbers are better even if that means you're not getting the top choice of the neighborhood you want to live in. House hacking can be as short as 12 months or as long as you want, so if don't get your top choice neighborhood you can out and onto the next property in 12 months. But  I think if you focus on the numbers more then neighborhoods you'll find a deal the pencils rather than limiting yourself to just a couple of neighborhoods. 

    The winter market is coming and you have the chance to get a good price on property that gets listed in the middle of the winter and not at the peak of the spring market. 

    If you need any help of guidance, I'm happy to connect.  

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

    @Rochelle Fernando you are correct that the delta isn't what it was three to five years ago. Most house hacks are more of a break-even situation when you find a "good" one, and you are mostly looking at the longer-term benefits of real estate like appreciation, depreciation and debt pay down. The main thing to remember is that real estate has always been a get wealthily slowly game. I think anyone who might move out of the area in a few years should not be looking as much at house hacking. If someone is from the Chicago area and has roots, it often times makes sense to buy a good building in an area you like versus renting. 

    The neighborhoods you referenced are all great spots. The rents have been absolutely on fire the past few years. We own in Avondale and manage in Logan Square, and the rental increases have been fantastic. That NW side is such a good, long-term area to own in. 

  • Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
    1y

    @Rochelle Fernando

    I agree with @John Warren. Go in with the expectation that in this current environment it's going to be difficult to break even, let alone positive cash flow. It's not impossible, but you need to (1) make improvements to the property & raise rents (2) take a longer time horizon (3) buy in "up & coming areas" on the fringes of more attractive neighborhoods. 

    It's way more challenging to get the numbers to work at higher price points. I've sold several house hacks in the past few months but they were all below $650k and did generate positive cash flow once fully rented under the assumptions the buyer will make cosmetic improvements and eventually rent out the units at market rates. And these were all in C class neighborhoods.

    Don't look for a home run deal in this market otherwise you will likely pass up decent opportunities. If you can reduce your housing expense by thousands of dollars over the course of a year, that's still a massive win.

    One strategy you can use to improve the numbers is to negotiate a large seller credit and then apply that credit to a rate buy down.

  • Eudith VacioPro Member
    Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
    1y

    Hey @Rochelle Fernando 👋🏽

    Great post and I've seen some of your previous posts on here, and I totally hear you on how tough the numbers are right now.

    One thing I’ve found works really well for 3-4-unit house hacks in high-rate times is to target properties that need a little TLC. If you can buy below market value, then put in modest improvements (paint, flooring, fixtures, maybe some minor updates on kitchens or baths), you can often increase rents enough to improve cash flow meaningfully. Use your owner-occupant financing to your advantage (lower rates/higher leverage) since you’re living in one unit. As of today, RATES ARE DROPPING! 

    If you buy smart, do a bit of work, you can convert “just breaking even” into positive cash flow sooner. Once rents stabilize and debt pay-down kicks in, your overall returns and risk profile improve.

    Happy to walk through some deal scenarios with you if you want to test this strategy!

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

    Rochelle - in this market, you must get creative. In a house hack, your objective is to lower your housing expense. If you save $1k per month by house hacking, it's worth it . That's $12k of after tax money per year. 

    If you're looking to maximize the return on your property, you need to find ways to boost cash flows. A few ideas: (1) short term rentals, (2) medium term rentals, (3) rent by the room. Some of my most successful clients that have strong cash flow, implement these strategies. 

    I would echo @Paul De Luca's comments about making improvements to the property as well. 

  • Victor SoBusiness Member
    Real Estate Agent · Chicago, IL · Member since 2017 · 325 posts · 193 votes
    1y

    @Rochelle Fernando like @Aaron Zimmerman mentioned, you have to get creative. I employ a combination of short-term, mid-term, and rent by room strategies to make my numbers work well. 

    Victor So Real Estate LLC517 Reviews
  • Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    1y

    I have lots of clients in similar situations. They focus on 3/4 units and then boost the rents heavily after buying. Do this by repainting cabinets, stone counter tops, fresh paint and adding in unit laundry. You do need some cash for the rehab but its not as costly as doing a full remodel. We have been hitting a good bit over $2000 now for 2/1s along the blue line neighborhoods like Avondale, Portage Park, etc. once you factor in those higher rents you can cashflow. The other option is just live in a unit a few years and wait as the rents go up and your mortgage stays the same, this also makes them cashflow higher and higher over long term. If plan to hold long term, view it as a long term play. 

    Also check out Albany Park, there are some cheapish 4 units and the rents here get very high once do some basic updates. 4s can actually get over 1% rule once factor in the ARV rents. Albany Park is my favorite area right now, I just offered on a place there for myself.

    Pretty much all over the north side you will get class A tenants even if in an area like Rogers Park, East Humboldt Park, Ukrainian Village, etc. so you don't need be in the fanciest part to get those great tenants where you can increase the rents annually. 

  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    1y

    Hi @Rochelle Fernando - Love your plan and vision!

    The way I always viewed it (because I had a similar vision) was if I could live in an awesome neighborhood and pay less for my portion of the mortgage than I would for rent it was a win!  I settled for 2 units in Logan Square and Bucktown.

    If you buy in those Chicago neighborhoods, you'll be good in the term as long as you aren't hurting for the cash flow.

    Purchase price will greatly depend on the condition of the property....are you looking at renovated properties or properties that need work?

    @John Warren nailed it!  It's more of a break even game short term...

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