I Let ChatGPT Pick Where I Retired — These 7 Places Were Shockingly Good
I’ve used ChatGPT for brainstorming, financial planning and to amuse myself with funny questions to bring humorous responses. So, why not give it a shot at planning where I retire?
It turned out that ChatGPT surprised me with its list of places for me to land for retirement. Read on to see why seven of the places it suggested turned out to be shockingly good locations to enjoy retirement.
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Here’s a bonus tip: If you want to give it a try, keep in mind that ChatGPT may default to listing places that are best for healthcare access for retirees. While that’s a good starting point, it means you’ll probably have to adjust your prompts a bit for more broad recommendations of places to look for retirement locations.
1. Pittsburgh
When ChatGPT listed Pittsburgh on the top of the list for places for me to retire, I was shocked. It’s not a city I’ve heard described as a top retirement destination before.
Still, ChatGPT liked the overall low cost and decent healthcare offered in this Pennsylvania city. In addition, it turns out Pittsburgh has affordable housing, good major hospitals and what ChatGPT described as “manageable pace.”
2. Greenville, South Carolina
When I hear the name of this city, it makes me think of a welcoming and hospitable place to retire. According to ChatGPT, it’s also an eastern retirement destination with low costs of living, decent healthcare, a mild climate and a growing downtown.
Something else that caught my eye about Greenville is the potential tax benefits of retiring here. It offers generally lower taxes than many other popular retirement towns.
3. Fayetteville, Arkansas
This is an inexpensive retirement city with good healthcare. That’s how ChatGPT sold Fayetteville.
For retirees looking for recreational activities, Fayetteville is known for its outdoor access. Here’s another potential selling point: It’s a place with “college-town energy,” according to ChatGPT. Since I grew up in a place much like that, I can appreciate that it brings lots of cultural and dining options.
4. Savannah, Georgia
I previously worked remotely for a company in Georgia. So when I saw Savannah on this list from ChatGPT, I was pleasantly surprised. After all, the people I worked with from Georgia were some of the nicest colleagues I’ve had in my career.
For starters, ChatGPT sold Savannah as a nice place with warm weather “without Florida extremes.” In addition, Savannah generally has pretty moderate costs and offers a walkable historic core.
5. Tucson, Arizona
The first western city recommendation from ChatGPT was Tucson. I wasn’t too surprised that part of the recommendation was based on weather, particularly the dry climate with excellent winter weather. As someone coming from the Midwest, I can appreciate that last part.
The surprising aspect to me was that ChatGPT noted Tucson having a “strong retirement community.” It turns out this city has lots of options to keep me entertained in my retirement years and that includes much more than just outdoor activities (such as cultural, social and dining opportunities).
6. Asheville, North Carolina
Let’s start with a bit of bad news about this retirement spot. Housing continues to grow pricier in the Asheville area. While that’s not enough to automatically delete it from the list of retirement spots, it’s a good thing to keep in mind.
The thing that made this location shockingly good in my mind was that it offers a great variety of benefits for retirees. For instance, there’s the gorgeous natural scenery. For those into the arts, there are plenty of spots to check out. Asheville is also known for the mild summers and winters.
7. Rochester, Minnesota
I’m going to be honest, the thought of retiring to Minnesota doesn’t immediately get me excited. I’m not into winter weather and cold temperatures.
But since ChatGPT listed Rochester as the top spot for retirees because of access to healthcare, I decided to check it out. It’s clear that Rochester is anchored by world-class medical care.
In addition, it was ranked among the best places to retire in 2025 by Forbes. In reviewing that ranking, I was pleasantly surprised to find the city offers an affordable cost of living with great amenities and low crime. Those are some pretty fantastic reasons to add it to the list of potential retirement places.
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