Chicago Trip Recap (November 05, 2013)


I’m back from my trip to the Windy City! And there are a few things worth mentioning. First off, this was a business trip, even though I did travel with a friend. Lately, my good buddy has been entertaining the thought of investing in rental property, and since Bay Area merchandise is sooooo expensive, he figured it would be a good idea to tag along and see what exactly it is I’m doing out of state.

So, we landed on Friday night and went on a property tour on Saturday. He got to meet the local grounds team and some other out of state investors.

Here are some of the properties we saw:




Total Teardown: Full Gut Job

As I’ve mentioned in numerous posts, I love these Chicago properties because of the extensive rehab the seller performs on them. This is no lipstick on a pig, but a full blown redevelopment. When the sellers obtain properties that are in dire straits condition, they don’t waste their time trying to restore it… rather, they rebuild it from the ground up. Once completed, you get new everything: copper piping, furnaces, water heaters, windows, countertops, sinks, toilets, laminate/tile floors, etc.




Distressed Property:

Other properties that are in bad condition.




Finished Product:

Some of the above pictures are downright scary to look out. Have no fear, once construction is complete (3-4 months), the newly re-developed property looks like this.





Very impressive, right? It’s no wonder I want another one of these properties… More details to follow in a separate post. Most likely, I will purchase another 2-flat unit in Chicago. This will be Rental Property #5. Also, my buddy was really impressed with everything: the operations, rehab, return on investment, etc. I’m pretty sure he’ll be picking up a property soon, as well.


Even though this was a business trip, we did make time to walk around Chicago and check out some of the sights.



chicago-18 chicago-19

This was my friend’s first trip out to Chicago… and it would be incomplete if we didn’t do the following…

Lou Malnati’s vs. Giordano’s

I was in Chicago, so I had to have some deep dish pizza!

You hear a lot about two places, in particular — Lou Malnati’s and Giordano’s. So, we decided to try both. I’ve had Giordano’s a few times before, but this was my first time trying Lou’s… and I gotta say, Lou takes the “cake” in my book! Whereas Giordano’s is more heavy on the cheese (and heavier, in general), I felt like Lou’s was the more balanced pie of the two. It’s got just the right blend of cheese, toppings, bread, sauce. Man, it’s some good stuff! Next time I’m back in Chicago, I’m heading back for sure.

Lou’s: (LHS)
Giordano’s: (RHS)



We also stopped by Milwaukee, for no rhyme or reason. Just wanted to see something different, and it’s not too far away from Chicago. Here are some pics.






Back in the Bay Area:

It feels good to be back in the warm Bay Area. It was freezing cold in Wisconsin and it rained quite a bit in Chicago on Saturday. As I picked up my luggage, I noticed something I hadn’t seen before at the airport terminal:

Yup, this is how I knew I was back in the Bay!


Print Friendly, PDF & Email
Sharing is Caring:
0 0 vote
Article Rating
Notify of
Newest Most Voted
Inline Feedbacks
View all comments
6 years ago

Looks like a great trip! I was just out in Chicago in the beginning of October and stood exactly where you stood in a couple of those pictures. Without a doubt my favorite city (that I’ve ever been to).

Good to hear you found another possible project to get involved with. Perhaps since you are running into issues with the banks due to the number of loans you have it might be worth having your buddy join in a few projects. Might create an opportunity for you, and him, to accelerate your purchasing even more.

6 years ago

What neighborhood(s) in Chicago are you looking at investing in? I live here and have been pondering investing in residential real estate recently, but have yet to really start the process. I have friends that have purchased properties on the south and west sides for Section 8, but most properties in the northside do not seem economical.

Also good call on Lou Malnati’s. Without question the best deep dish.