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Akeem Watson
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  • Chicago
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House hacking in Chicago neighborhoods

Akeem Watson
  • Investor
  • Chicago
Posted Apr 13 2024, 21:55

Hello everyone,

I am moving to Chicago soon and looking for great investments to house hack. Would it be a good investment to buy in southshore, woodland or Chicago lawn?


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John Warren
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#1 House Hacking Contributor
  • Real Estate Broker
  • 1658 N. Milwaukee Ave Ste B PMP 18969 Chicago, IL 60647
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John Warren
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  • 1658 N. Milwaukee Ave Ste B PMP 18969 Chicago, IL 60647
Replied Apr 14 2024, 04:20

@Akeem Watson you can make money anywhere in Chicago as long as you know the areas and are comfortable with them. The south side tends to be a place where the people who make money are very rooted in the communities they invest in. Operations is where you make your money. The building inventory is pretty spectacular in those areas, so there are always amazing buildings you can buy and renovate. 

Do you know the neighborhoods? If you are comfortable with them, then yes, you will do great. 

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Mark Ainley
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  • Property Manager
  • Roselle, IL (Chicago Suburb)
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Mark Ainley
Property Manager
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  • Roselle, IL (Chicago Suburb)
Replied Apr 14 2024, 05:55

@Akeem Watson is shared this post with a few brokers in our office who might have inventory coming up that you can check out first.  

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Akeem Watson
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  • Chicago
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Akeem Watson
  • Investor
  • Chicago
Replied Apr 14 2024, 06:11

Thank you for the responses. I have been touring to get familiar with all the neighborhoods. @Mark Ainley thank you so much, that would be great. My ideal location would be north woodland close to Washington park 

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Paul De Luca
  • Real Estate Agent
  • Chicago, IL
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Paul De Luca
  • Real Estate Agent
  • Chicago, IL
Replied Apr 15 2024, 06:29
Quote from @Akeem Watson:

Hello everyone,

I am moving to Chicago soon and looking for great investments to house hack. Would it be a good investment to buy in southshore, woodland or Chicago lawn?



Depends on what your buying criteria is - budget, ROI, neighborhood class, etc all need to be considered. The quality of each of those neighborhoods is block by block. Niche.com is a great tool for gauging the quality of a neighborhood and South Shore, Woodlawn, and Chicago Lawn are all considered C class. I've sold a few buildings in those areas and you can find decent opportunities.

South Shore in particular has very large 2-4 unit buildings from what I've seen. They often have units with well over 1000 square feet and oftentimes 3-4 beds/2 baths per unit which is great for getting stronger rents. I analyzed a few house hack deals there recently though and the numbers didn't look promising post move-out. But if you analyze enough deals you can probably find the right fit. 

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Jonathan Klemm
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Jonathan Klemm
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ModeratorReplied Apr 16 2024, 07:44

Hey there @Akeem Watson!  Welcome to Chicago my friend!

Where are you moving from?

I think house hacking neighborhoods will depend on your price point and level of comfort in different neighborhoods.  I love that southeast corridor of south shore, woodlawn, washington park, bronzeville, etc. is amazing!

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Kevin Garvey
  • Realtor
  • Chicago, IL
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Kevin Garvey
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Replied Apr 16 2024, 13:02
Quote from @Akeem Watson:

Hello everyone,

I am moving to Chicago soon and looking for great investments to house hack. Would it be a good investment to buy in southshore, woodland or Chicago lawn?


Welcome to Chicago! 

Chicago Lawn is a much different area than Woodlawn or south shore - there are a lot more single family and small 2-4 unit properties, and the area is less dense generally. 

Woodlawn is seeing some price increases lately due to new investment and the Obama library. Jackson and Washington parks are always a huge selling point, as well as the proximity to university of Chicago. 

South Shore , as someone mentioned, has a lot of very large apartments in the 2-4 unit buildings in the area. 

I’ve been working all over the southside for years and it comes down to knowing the block and the surrounding blocks. It’s good to get involved with the neighbors and neighboring institutions as well. 

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Jack Matthias
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Jack Matthias
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Replied Apr 17 2024, 12:45

If and when you have questions about financing in the Chicagoland area I would be happy assist. Knowing what to expect for closing costs in Chicago is a big one.

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Crystal Smith
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Crystal Smith
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ModeratorReplied Apr 18 2024, 03:10
Quote from @Akeem Watson:

Hello everyone,

I am moving to Chicago soon and looking for great investments to house hack. Would it be a good investment to buy in southshore, woodland or Chicago lawn?



The southshore, woodland and Chicago lawn are great areas for investment and house hacking. Following is my opinion but I recommend you get the feel of the neighborhoods.  Of all the areas I like Woodlawn the best.  (Just because I like it the best does not mean there are not opportunities in the other communities.) For Woodlawn- The closer you can get to the University of Chicago the better.  If you're able to purchase a multifamily close to the school it opens up the possibilities of using the units for traditional long-term rent, renting to students or AirBnB. 

The South Shore is continuing to morph.  It's a block-by-block play that in my opinion & requires a visit so you can determine where you feel comfortable and also to ensure that you situate yourself where shopping (grocery shopping) is closely available. 

Chicago Lawn is also a block-by-block play. Some blocks are great while others may not be as great.  What do I mean by great. A great block to me only has one bad property on it, while the remainder is pristine.  Now if you can afford to purchase all the bad properties on a block then it doesn't matter.  By the way- It's possible.  We did that a couple of times.


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Replied Apr 18 2024, 16:01

For example, investing on the south shore may offer affordable property prices, but it may also come with high crime rates and a less stable environment. Wooded areas can be attractive to those who value nature and a quiet environment, but the cost can be higher. Chicago's lawn offers a variety of options, including residential areas with good amenities.

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Jacopo Iasiello#2 Market Trends & Data Contributor
  • Investor
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Jacopo Iasiello#2 Market Trends & Data Contributor
  • Investor
  • Miami Beach, FL
Replied Apr 19 2024, 05:08

Hi Akeem, depends on various factors, including your investment goals, budget, risk tolerance, and preferences these are some basic questions to answer.