Chicago's Greater Grand Crossing Area

13 Replies

Does anyone have experience with Chicago's Greater Grand Crossing Area? I'm curious if it would be a good location for a new investor. 

Thanks in advance for any insight!

Updated 12 months ago

FYI - this is in regards to buying rental property.

@Michael Boyle If this is your first flip, I would stay away from the city. The area itself is a C neighborhood and you won't have a problem selling it if the rehab was done correctly. However, the city of Chicago requires a ton of permits and it becomes very expensive. The permits also take forever to get approved and you will need an expediter.  Properties in the neighborhood typically require a gut rehab as they are extremely old homes. Which is something I wouldn't do if this were going to be my first rehab.

Thanks Daniel.

This is actually regarding potential rental property. Does that change things?

Let's assume rehab isn't an issue. I'm more worried about the ability to get and keep renters.

@Michael Boyle It's a strong cash flow area. You should hire a very good property management in place if you end up buying a property in the south side. 

That's good input. Sounds like it has potential.

Thanks again Daniel!

this area is being gentrified. It depends on the block as there is some moderate crime in the area. Some blocks are quiet and in great shape overall. Some aren’t. 

There could be a good deal in the area but as Daniel said flipping in chicago can be a real pain. You have to constantly get approved While rehabbing. For example if you’re approved to rehab the electrical the city must come back and make sure everything is up to code. Then you could move onto plumbing but only until they say it’s ok. Otherwise you will get fined.

Also check if there are any violations on those houses. Many old houses in Chicago have violations with the city. Check the water bill as well.....Flipping in Chicago in general should not be taken lightly at all. Maybe have a partner who has experience go into your first couple so that you have the experience. 

Thanks Elbert.

Actually this was in regards to buying rental property not flipping houses.  

Still good input though-thanks again. 

I have a property in GC. Overall its a mixed bag but their are some positives. Such as...

People who know and live in the area claim it has much improved in the last 10 years.

90/40 runs right through it so its offers easy access to and from the city for residents who commute by car.

The train runs along 90/94 so it has good train service to and from the city and to connecting lines.

All major roads from 63rd to 79th have good bus service and also feed the train lines. So residents/renters have good options for public transport. 

To the south is Chatham, a decent area with great housing stock, nice neighborhoods and good commerce with malls and shops offering both employment and social amenities. 

To the west is Englewood which has been much touted by the City and the press as an area for positive redevelopment. 

A big consideration would be what type of rental property are you considering ?   2 Flat, 4 Flat, a big Multi ?    That would make a big difference as to the type of strategy you need to adopt.

And as other have mentioned if you are not from the area or familiar with the area you need solid local management that can check both of those boxes.   

I have a property in GC and while it has had its challenges so far I have no big regrets. But I have a great local team and  very specific guidelines and criteria with regards to the type of properties that interest me. 


That's a lot of great information about the area Ronan. Have you been in that area long? Sounds like you really know it well. Regarding transportation and access it sounds like a good investment location. I'm in the west suburbs so it's not too far from reach for me.

As for me I was interested in buying a multi-unit. Seems like good way to spread rental risk among units. Of course possibly more headaches as well...

As far as property management goes, originally I was for it, but then I read some horror stories. I'm a little nervous about signing a contract and getting tied to a company for a long period of time. 

@Michael Boyle well that’s the thing does the properties your looking at work better good as a rental? Does it work good as a flip? Not every property cash flows and not every property is a good flip. You have to run numbers to see if it does or not. 

Hi Elbert! For me a rental makes the most sense right now as I'm looking for steady cash flow. 

But regarding the building's best I'm looking at I'm still waiting to tour the property. I won't really know what I'm dealing with until I get on site. There are a couple of units I know that need to be rehabbed but I don't know the cost yet. From a numbers standpoint it definitely appears that it could be cash flowing before those units are rehabbed. If that is the case my idea was to hold it while updating the remaining units. After that I can make a judgement. My personal preference right now is to hold. And as you and others have said - flipping in that ares could be tough especially when a rehab is needed.


Seems like every unit I visit has some problem with the tenant. I have noticed that several of the owners don't seem to enforce the lease very firmly. Could that be part of the reason for their failure? Maybe they don't screen well enough? Are they too lax with the tenants?

@Ronan M. Would you consider GC a war zone? Any areas you would stay away from (north, south, east, west)?

No I would not. Its not Beverly Hills but its not a war zone either.

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