Best Area in Chicago to Purchase Rental Property

16 Replies

Hi All

I purchased my first multi unit 9 years ago and looking to dive back in and purchase more property. My rental property is on the southside of Chicago and looking to possibly purchase on the North or West side of Chicago. What areas do you suggest??

@Tanisha Blakemore  the obvious choice for me would be the Lincoln Park/ Lakeview areas, if your budget can afford that. These two areas can provide the best renters but you may pay for what you get. The Edgewater/Rodgers park area on the north side of the city is a good area, and provides some opportunity. On the west end, Logan square could be a good area to find a deal as well. Are you looking to get another MFH?? 

@Josh Mitchell those areas are definitely on my radar. I actually would love to move to that area myself, that's definitely an option. 

I am weighing my options,  trying to see what's more beneficial. 

Option 1:Purchase a 3 to 4 unit in that area and reside in one unit and rent the others. Which will include additional rent from the unit that I live in now on the south side.

Option 2: purchase a single family home to rent in another area. Along with my fiance purchasing a property for us to reside in (he will have the perks of being 1st time home buyer) and renting the my 2 unit on the south side,  1 of those units producing cash flow.


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@Tanisha Blakemore in the city, again depending on where you are wanting to be, I think the MFH would be the way to go. (Option 1) Live in and rent out you could do an FHA loan as well if you plan to be there for a little while. Could get the loan for 3.5% down.

Southside has potential because prices are still low. Depends if you're looking to flip or buy and hold. As far as tenants, you have to do in depth screening. Overall there is opportunities there.

@Tanisha Blakemore  I agree with  @Josh Mitchell   Much more cash flow potential as long as you're willing to live in a MFH with tenants. But you could always crunch the numbers and see what say.
Lincoln Park has always been really nice. 
Logan Square definitely has some opportunities. 

I was just in Ukranian Village and fell in love with that area. 
How is Ravenswood & Albany Park? Those areas seem really nice, quite, and more affordable compared to Lincoln Park & Lake View. 

Don't rule out the suburbs as well.
Comparable clientele as south side but less headache and cheaper prices. Keep in mind it's all cook county so the rental aspect/pricing is the same.

I would say looking in the South Surburbs that would be a great place to start, prices are fairly resonable, great working class neighborhoods and neighborhoods are family oriented. Another decent area is the woodlawn/hyde park area this area can be tricky but with a really in- depth search you can find some great deals.

Thanks all!! Honestly I have considered all areas. I was in Wicker park today and I LOVE the area. Any of the areas up north are really nice. Wicker, Bucktown, Ravenswood, Lakeview, etc. The more time I spend up there the more I'm considering purchasing there for my next property.  I don't have a problem with residing in same bldg as tenants.  That has been my current situation for the past 9 years. I'm now ready to get more bang for my buck including enjoying the area as well, though purchase price maybe more. I have rubbed off on my fiancée so he'll be looking to purchase as well.

Which is another question I have?? Better for us to purchase one together or 1 each separately?? He's gets the 1st home buyer perks. 

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Hi Tanisha:

Not sure if you have decided which Chicago neighborhood suits your fancy, but there are a number of really great deals on 2, 3 and 4-flats in Woodlawn and west South Shore, particularly if you and your fiancee are planning to live in one and rent the others.  I work with a lot of clients who use that strategy to leverage owner occupant financing while defraying the cost of their mortgage. I just posted a 2-flat for rehab on BP that would fit that model...but others abound.  Please let me know if you'd like to discuss further.

I am looking heavily in the Chicago area now. How are you all offsetting the high tax rates in some areas; i.e., Beverly, Hyde park, etc...? How does it affect the ROI on the buy and hold rentals?

Thank you?

@Felicia Bell

Always been interested in the South Shore. Much of it looks like the North Shore, but at bargain basement prices... I do think it has a couple years to go, but not a bad play if you can hold on or know the area well.

For my money, Roger's Park is the best game in town. I feel like properties there are always undervalued, compared the great access and community it offers. Disclaimer, I did grow up in Evanston, and have always wanted to get into the Roger's Park market. My friends who own multi family units there do pretty good. 

Have you checked into the average time to Eviction in Cook County and in Chicago? That was enough to keep me out of Cook County altogether. I suggest you ask the Sheriff how long that process is right now. 

Also reach out to a local eviction attorney to find out how long it takes to get the Writ of Eviction authorized by the judge once you file. Then compare to other locales.