I Asked ChatGPT Where Social Security Checks Go the Furthest in Retirement

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Getting the most from your Social Security benefit in retirement is important, especially if you don’t have a lot of savings to rely on. I asked ChatGPT to find the states where your Social Security check will go the furthest — here’s what it said.
The ChatGPT Prompt
Here’s the prompt given to ChatGPT to find out where social security checks go the furthest in retirement.
List five states where social security checks provide the highest standard of living in retirement. Factor in the average benefit payment and the cost of living.
The ChatGPT Response
ChatGPT said there are five U.S. states that tend to offer retirees a relatively high standard of living on Social Security alone, based on comparing average benefits, cost of living and favorable tax/taxation of benefits. The best states are those with a good balance: decent Social Security benefit amounts, plus low costs, plus favorable taxes for retirees.
Key Points ChatGPT Highlighted
- The average (or median) Social Security benefit differs by state; some states have higher average benefits simply due to higher lifetime earnings.
- The cost-of-living index varies a lot from state to state. States with lower cost of housing, utilities, groceries etc. allow a given benefit to stretch further.
- Also, whether the state taxes Social Security benefits or other retirement income matters. Many states do not tax Social Security, which helps.
Five States That Look Especially Good for Living Well on Social Security
Here are five states ChatGPT said tend to score well when you put all of those factors together. Of course, much depends on your lifestyle, health needs, local housing, etcetera, but these are strong contenders.
State | What makes it good for retirees living mainly on Social Security |
Mississippi | Lowest cost of living of any state (housing especially cheap) so your benefit goes far. Also, Social Security benefits are not taxed by the state. |
West Virginia | Very low cost of living; also moving toward eliminating state taxation of Social Security for all retirees. |
Arkansas | Among the cheapest states to live in; plus, Social Security is exempt from state income tax. |
Oklahoma | Low overall living expenses (housing, etcetera) and favorable tax treatment for retirees. |
Alabama | Affordable cost of living, no tax on Social Security benefits, relatively decent average benefit vs. what costs will be. |
A Deeper Dive
After returning this list of the top 5 states, ChatGPT offered to provide more detail, along with a list of the top 10 states. Below is what the artificial intelligence (AI) chatbot said.
“Here’s a more systematic ranking of U.S. states by how far an average Social Security benefit goes, adjusting for cost of living and state taxation of Social Security benefits.” With that, ChatGPT shared the top 10 states based on standard of living on Social Security alone.
“Here are about ten states that tend to come out on top, followed by commentary. Depending on your priorities (taxes, housing, climate, etcetera), some may fit better than others.”
Rank | State | Why It Does Well (Pros) | Some Possible Drawbacks |
1 | Mississippi | Very low cost of living (especially housing) + no state tax on Social Security benefits. Even though average benefit is on the lower end, the low cost and favorable tax treatment make it stretch far. | Lower average incomes sometimes correlate with more limited services; health care access or quality may vary depending on region. |
2 | Alabama | Similar story: modest benefits but low housing, utilities etc.; Social Security not taxed by state. Cost of living index among the lower states. | Some areas may still have relatively higher property or sales taxes; depending on how “rural” vs “urban,” cost differences. |
3 | Oklahoma | Among the cheapest in cost‐of‐living indices. Combined with no tax on SS benefits, this makes it very strong. | Some parts have hotter weather, which can increase utility bills; also, job/amenity access may be less in more rural parts. |
4 | Arkansas | Low cost of living, SS benefits are exempt, moderate taxes overall. | Some rural infrastructure and health care access issues depending on location. |
5 | Missouri | Quite low cost of living (one of the lowest per MERIC) and no SS state taxation. The average benefit is mid‐tier. | In some urban or suburban areas costs creep up; state taxes or other local taxes may reduce benefit somewhat. |
6 | Iowa | Reasonable benefits, low‐to‐moderate cost of living and favorable tax treatment. | Winters are harsh; for those sensitive to heating costs or weather, that could add to expenses. |
7 | Texas | No state income tax at all, so Social Security gets preserved; many areas with moderate cost of living (though there are expensive metros). | Housing in high‐growth parts (e.g. Austin, Dallas) is rising; property taxes may be high; local costs vary widely. |
8 | Florida | Favorable tax status (no state income tax) and many retirees choose Florida in part because other costs (in many places) are relatively moderate. | Some parts (coastal, tourist zones) are expensive; insurance (e.g. hurricane) and healthcare costs in certain areas can be high. |
9 | Tennessee | No state income tax; lower cost of living in many parts. SS benefits untaxed. Good mix. | Sales taxes & local taxes, depending on county/city, may be substantial; some rural areas may have fewer amenities. |
10 | North Carolina | Decent average benefits, relatively moderate cost of living in many areas, no SS state tax, reasonably good infrastructure. | Coastal areas and popular retirement regions are getting more expensive; weather (hurricanes etc.) might be risk for some. |
ChatGPT provided some interesting information about where you may get the most from your social security benefit. Keep in mind that the information generated by ChatGPT may not be accurate, so be sure to do your own independent research using reputable sources before making any decisions. And engaging a financial advisor to help talk you through your options is often a worthwhile investment.