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Key Takeaways
- The best big cities for retirees in the U.S. are Miami, Florida; Chicago, Illinois; Pittsburgh and Philadelphia in Pennsylvania; Nashville, Tennessee; and Houston, Texas.
- Retiring in a big city provides options for free or low-cost entertainment, large airports to save money on travel, and plentiful healthcare access.
- Big cities are often highly walkable and have robust public transit systems, allowing retirees to save money on transportation and reduce the need to drive while aging in place.
- Housing costs are often higher in large cities, especially in desirable neighborhoods.
- Retirees must carefully weigh the access and financial perks of big-city living against the higher costs of living and housing prices.
Retirees looking for the best place to spend their retirement have many options, from small towns to suburbs to heading abroad. Big cities, those that have a population over 250,000, come with specific financial and lifestyle benefits. But for some retirees, those benefits may not be enough to outweigh the crowding, cost of living, and busy pace of life.
6 Best Big Cities for Retirees
According to Investopedia’s research and rankings, the six best big cities for retirees in the United States are:
- Pittsburgh, Pennsylvania
- Philadelphia, Pennsylvania
- Chicago, Illinois
- Houston, Texas
- Nashville, Tennessee
- Miami, Florida
Financial Benefits of Retiring in a Big City
Retiring in a big city can come with a variety of lifestyle benefits, many of which create financial advantages as well.
Low-Price or Free Entertainment Options
Big cities have plentiful arts and entertainment options, often with more free options than can be found in smaller towns or suburbs. In Philadelphia, for example, the Curtis Institute of Music offers more than 100 free performances a year, many of them by the professional musicians in the faculty or students who are about to graduate and begin their professional careers.
Retirees in big cities can enjoy world-class cultural entertainment while still being budget-conscious.
Walkability and Public Transit
Big cities generally are more walkable than towns or suburbs, as well as having more public transit options. In some cities, retirees may not need to own a car at all. Many cities also offer free or reduced fares for residents over a certain age. In Miami, for example, Medicare recipients and those with disabilities are eligible for discounted fares.
This lack of dependence on car travel lowers retirees’ monthly transportation costs, along with increasing their independence and making it easier to age in place.
Travel Access
Big cities aren’t the only places with airports nearby. However, they are more likely to have airline hubs or large, international airports. This means retirees who regularly travel have more flight options to choose from and can pick the best option for their budget, rather than the only flight available from a small airport.
Big cities are also more likely to be large hubs for train travel, with major Amtrak stations and plenty of travel times each day. Of the cities on this list, only Nashville doesn’t have its own Amtrak station downtown.
Healthcare Access
Big cities often have easy access to multiple hospitals and healthcare facilities. Nashville, for example, has more than 10 hospitals within its city limits, making it easier for retirees to access both primary and specialist care without long wait times or the need to budget for travel.
By contrast, rural counties are more likely to face shortages of primary care professionals, and residents must often travel to hospitals in other areas to receive acute or specialty care. Transportation challenges, which can impact retirees who are aging in place, can also make healthcare services more expensive and difficult to access in rural areas.
Financial Drawbacks of Retiring in a Big City
Big-city living can also have drawbacks for retirees living on a fixed budget, particularly when it comes to everyday expenses like utilities and housing. However, higher costs for some expenses may be offset by other factors, such as Florida’s lack of state income tax or Philadelphia’s comprehensive public transit options.
Cost of Living
Daily living costs in big cities are often high. Miami’s average cost of living, for example, is 20% higher than the national average, while Chicago’s is 17% higher and Philadelphia’s is 7% higher. (Pittsburgh, Nashville, and Houston all have a cost of living that is lower than the national average, though not by much, at 2% lower in Pittsburgh and Nashville, and 6% lower in Houston.)
Housing Prices
Downtown in big cities is often the best place to take advantage of the lifestyle benefits of city living. But depending on the city, the cost of housing can be steep. Philadelphia, Pittsburgh, Houston, and Chicago all have average home values slightly under the U.S. average of $357,445. But the averages are significantly higher in Nashville ($426,126) and Miami ($569,760).
Retirees may also find that the most desirable neighborhoods to live in are the most expensive, regardless of the city’s overall average. In Philadelphia, the popular Fitler Square neighborhood has an average home value of $650,000.
The Bottom Line
Moving to a big city can provide retirees with affordable options for culture and entertainment and easy access to airport or train travel. The walkability and public transit options in big cities can help retirees stay independent without relying on a car to get around, and big cities tend to have plenty of healthcare access, including to specialty and acute care. Some of the best large U.S. cities for retirees are Pittsburgh, Philadelphia, Chicago, Houston, Nashville, and Miami.
However, many big cities also have high costs of living and expensive housing, especially in desirable neighborhoods. Retirees who choose to live in large cities must budget carefully and decide whether the amenities and busy lifestyle outweigh concerns about affordability.

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