House Hack Chicago

Created by Henry Lazerow investor/agent with Fulton Grace Realty over $60 million of Chicago 2 to 4 unit properties sold and counting!

I built this site to help Chicago house hackers. Here, I share real life deal diaries and practical tips for this market.

Even if you're not a client, feel free to email me with questions about house hacking or running rentals in Chicago. I'm always happy to help.

My background

Hi, I am Henry Lazerow. My first entry into the industry was as an acquisitions analyst with a small syndicator after college. My entrepreneurial drive led me to invest on my own, so I bought a four unit property in Rogers Park as a house hack and later turned it into a BRRR. This deal showed me the demand for an investor-friendly agent, I decided to focus full-time on brokering two to four unit properties and here we are today! Unlike most agents, I focus exclusively on two to four unit properties and select investment condos. This focus has helped me stand out and become an expert in the small-investment niche.

Areas we cover

I work in the neighborhoods I believe in, including the entire North Side, parts of the Southwest Side, and Bronzeville. I look for areas experiencing growth with low supply, where I expect rental rates to increase faster than inflation and where my clients can find tenants with good credit who take care of their units. This creates sustainable, long-term investments. By focusing on specific areas rather than the whole city, I know the ARV and max rental rates by block and have expert knowledge of these neighborhoods.

I have a list of trusted, repeat contractors and handymen in these areas whom I recommend to clients.

Property Marketing

I have a unique strategy. I typically list properties on Thursdays, market them heavily, and do not allow first showings until a group showing time over the weekend. My team helps me run these open houses smoothly and we work every lead aggressively. This group environment builds competition, resulting in record-high offers and allowing us to pick the strongest offer, while also having back up offers. Using this strategy, I have set two Chicago area multi unit records: one in Lincoln Park for a 3 unit and another recently for a legal two-flat with an in-law unit in Avondale. I discuss the whole sales process with all tenants in advance and, most importantly, keep them happy throughout the sale.

I advise my clients on listing prep work. This often includes unique considerations for multifamily properties, such as structuring leases to appeal to owner-occupant buyers and making strategic updates to maximize rents if we decide to increase the rent roll before listing.

Property Analysis

I review each deal analysis with my clients and provide vacancy rates and expected operating costs for each area. I use a discounted cashflow spreadsheet that I custom built, but the most important part is entering accurate variables. I understand these variables well from owning my own properties and overseeing my clients’ investments.

I also provide a list of updates to consider after you buy. In-unit laundry is one of my favorite improvements because it can turn a basic rental into a desirable, higher-priced unit that attracts better-quality tenants. Understanding your plans for the building is very important when conducting an accurate analysis.

What Our Clients Say

I met Henry through a real estate meet up event. He knows the area I was looking at very well, down to block by block level. He also is very investor friendly, detailed-oriented and amazingly responsive to all my needs and questions. There is no time that I couldn't reach or ask him for advice on all the deals we were looking at. And I do constantly ask lots of questions.
Henry has helped me to close 4-unit building in Logan Square with my strict criteria after few months looking non stop on the market.

If you are an investor focusing on small multifamily, Henry is your go-to-guy as he really understands what investors are looking for.

Ton Trieu

Henry helped me with a purchase that was a 1031 exchange and a loan assumption from a single condo to a 3-flat multifamily. The process itself was hairy due to the different requirements, but Henry saw us through to a good ending and acquisition. As an investor and landlord himself, he has a lot of experience and contacts that have proven invaluable in my management of my new multifamily.

Charles Liu

If you are in the market for an investment property in the Chicagoland area, Henry is your broker. He helped me close on a 3 flat in the West Town area. I would highly recommend him if you are looking for a broker who is very responsive, data driven, a team player and a strong negotiator.

I was very impressed with Henry during our first encounter because he knew about "good" and "bad" areas down to the block in my target area. Additionally he built a spreadsheet that was easy to comprehend which covers internal rate of return, cash flow, appreciation and exit strategy. Because of his industry knowledge and business acumen, I felt I was in good hands.

When we identified a property to put an offer on, he demonstrated that he was a strong negotiator by getting me a better price than I was willing to pay for. The property was listed at 549k and the numbers would have made sense at 530k, however he got me a final price of 522.5k.

Again, I would highly recommend Henry when purchasing an investment property in the Chicagoland area and I cannot wait to work on the next property with him!

Summary:
-Very responsive: email, text, I know I get can get the support or answers I need.
-Data driven: IRR, cash flow, appreciation, exit strategy
-Team player: works well with my lender, attorney, seller's agent.
-Strong Negotiator: 549K property to 522.5K

Brian Nguyen

Henry Lazerow has proven time and time again to be an incredible asset to the real estate community in Chicago. I reached out to Henry after reading through his many informative posts on the BiggerPockets forums. Despite his busy schedule as an investor-friendly real estate agent, Henry is readily willing to take time out of his day to mentor others through his personal experience, references, and knowledge base. As a result, he helped me close on my first duplex and continues to be an excellent resource throughout my renovation process. As a local investor, I can’t thank him enough for being someone I can count on. Regardless of whether you are a new or seasoned investor, anyone would be lucky to have Henry on their team. I would not hesitate to recommend Henry as an agent who is creative, knows the market, and is numbers-driven. Henry will not steer you wrong.

Kris Toribio

Henry was representing me for my first real estate purchase. He has a thorough knowledge on different neighborhoods in Chicago and is very fast in getting back with updates! I love how transparent he was with the whole process. Being out of state investor looking for property and going through the closing was already challenging and Henry acted as my delegator and took care of tasks like inspections. I thoroughly enjoyed working with him and would totally recommend him to anyone who is looking for properties in Chicago area!

Ayush Vijaywargi

Henry did a great job getting us an investment property. He was aggressive and put the property under contract very quickly. We recently used him for a second time.

Andrew Marx - Athens Investments founder