Lawyer Moved to Puerto Rico From Chicago, Pays More in Rent

This as-told-to essay is based on conversations with Michael McCready, 56, a lawyer who moved from Chicago to San Juan, Puerto Rico, in January. The conversation has been edited for length and clarity.

I’ve been a personal injury lawyer in Chicago for 30 years, and on January 1st, my wife and I relocated to Puerto Rico permanently as residents.

What got us to that point was I’m 56, and we started talking about me being out of the active practice of law at 60 and traveling. My wife said we still need a home base. That was the main impetus for looking into moving to Puerto Rico.

We absolutely fell in love with Puerto Rico and we’ve been living here for seven months now. I come back to Chicago periodically to run my office, and I speak around the country, but Puerto Rico is our home and I have nothing but positive things to say about it.

Homes are actually more expensive in San Juan than on the mainland

The areas that the expats like myself live in tend to be pretty pricey. I’m paying more renting a place now in Puerto Rico than I was in downtown Chicago. I was quite surprised at that. But that’s probably a function of where I’m living.

There are essentially two places that most people from mainland end up: One is Condado, and that is where all the restaurants and nightclubs are — in Chicago, it’s the equivalent of River North. It’s where all the young rich people are and where everything is happening.

The other location that a lot of people from the mainland gravitate towards is Dorado. It’s is about a 30- to 40-minute drive from Condado. It is a Ritz-Carlton gated community with beautiful homes starting at $2 million and probably going up to $20 million.

We live in Condado and we’re very happy there.

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We’re renting right now, but most of the properties that I’m interested in buying are probably in the $1,000 per square foot range — but there are new buildings going up that are being listed at $2,000 a square foot.

We are in a three-bedroom, two-bath apartment of maybe 1,900 square feet, and we’re paying $6,500 a month.

In Chicago, we had a three-bedroom, three-bathroom, 2,300 square-foot condo on Michigan and Randolph. We looked out over the Lake Michigan, 35th floor, and we were paying $5,000 a month. So, I was surprised at the price for rentals.

Chicago was a little bit bigger — and certainly a better location. We loved our location in Chicago, but we’re also now three buildings from the beach. So we’re going to pay a premium for that and the area that we’re in. But it’s certainly more expensive.

When I’m sitting around doing work at home and most people are going for a coffee, I just walk outside to the beach for 10 minutes and soak up the sun.

There are a few unexpected quirks to living in Puerto Rico, but it’s not that different here

First, it’s between 70 and 90 degrees all year round. The coldest day on record in San Juan was 64 degrees, and the hottest day on record was 96 degrees. Compare that to Florida. I was in Florida when it was in the 50s and it was freezing. And then Florida can hit 110 degrees. So can Texas and Arizona.

So, it’s similar to Hawaii in that it stays the same temperature year round. If I go on my weather app right now, it’s going to say 77 to 87 degrees for the next 10 days.

It’s really nice. It doesn’t get too hot and it never gets too cold. It’s humid, but not like Florida-humid. So, the weather is fantastic.

There are wonderful restaurants — which was a great surprise coming from Chicago. Any ethnicity that you want, and then very, very high-quality fancy restaurants.

Chicago is a very clean city, and San Juan — and I’m talking specifically the San Juan area — is not the cleanest. There’s graffiti, but that’s typical of a lot of other urban areas.

I just came back from Portugal, and they get graffiti everywhere.

The infrastructure on the island has certainly been neglected — you’ve probably heard about their power struggles.

I was there on New Year’s Eve and the power went out. I was there at Easter and the power went out. And it was out for two or three days.

The power went out almost across the island. My son and I were driving to the eastern part of the island on New Year’s and none of the traffic lights were working and all the restaurants were closed. Nobody had any power.

Where I live, we all have full building generators. So when the power goes out, it literally goes and comes right back on. So there was absolutely no disruption for us. But there was for a lot of people on the island. If you’ve got no air conditioning and you’ve got no electricity for three days, your refrigerator, your food is gone, you’re sweltering.

Groceries tend to be a little bit higher priced. Apparently, there’s some law that says food has to go to the US mainland first before it comes to Puerto Rico. Even if they could get something from the Dominican Republic, it has to go through the mainland in order to get to Puerto Rico. And that transportation cost is going to be reflected in the cost of goods. But there’s a Costco here, and Amazon delivers here.

There’s really not much difference than living on the mainland. We’ve been there for seven months now, and that experience has proven correct.

It’s been a fantastic move for us and we couldn’t be happier.