The Underappreciated Midwest Retirement Cities With Great Quality-of-Life Scores

By Leo Sun – Feb 27, 2026 at 3:47PM ESTKey PointsSt. Paul and Minneapolis pair high quality-of-life scores with a low cost of living.Chicago is surprising affordable for a major U.S. city.Milwaukee is even more affordable than those three Midwest cities.According to The Motley Fool's Best Places to Retire Index, Florida, California, and Texas are the three best states to retire in. Florida and Texas have lower taxes and a lower cost of living than many other states, while California ranks highest in quality of life. As a result, many retirees might overlook the entire Midwest region. But according to our index, several Midwestern cities have above-average quality-of-life scores and a below-average cost of living. Let's review four of those cities: Saint Paul, Minneapolis, Chicago, and Milwaukee. Image source: Getty Images. Saint Paul and Minneapolis, Minnesota Saint Paul and Minneapolis, the "Twin Cities" of Minnesota, have the two highest quality-of-life scores (out of 100) of 67 and 57, respectively. Minneapolis is the bigger sibling, with a population of nearly 430,000, while Saint Paul is the smaller twin, with about 310,000 residents. Minneapolis, with its younger population, is more modern, artsy, and business-oriented than St. Paul, which is quieter, more historic, and geared toward families and retirees. The locals often say Minneapolis feels like a small city, while St. Paul feels like a big town. A light rail connects both cities to the Minneapolis-St.

Paul International Airport and each other. Minneapolis is more walkable and bikeable than many other comparable cities, and it offers a wide range of retail establishments, dining options, and cultural amenities. St. Paul offers an extensive park and trail network, plenty of community programs for seniors, and a lower cost of living (79) than Minneapolis (74). Both cities have the same, relatively safe crime score (74). Saint Paul and Minneapolis share the same problems: harsh winters and high city taxes. Saint Paul's focus on preserving its historical appeal tends to hamper its economic growth, while Minneapolis struggles with pockets of crime in certain areas. Moreover, the recent conflicts between ICE and residents could be driving away lots of potential retirees. Chicago, Illinois Chicago, the most populous Midwestern city with 2.7 million residents, might not be considered an ideal place to retire. However, it still has the third-highest quality-of-life score (57) among Midwestern cities with a relatively affordable cost of living (74). Chicagoans can access a wealth of cultural attractions, including the Field Museum and Art Institute of Chicago; world-class healthcare facilities at Northwestern Memorial Hospital and the University of Chicago Medical Center; and plenty of dining, shopping, and retail establishments. Chicago's crime score (76) also technically makes it safer than St. Paul and Minneapolis, even though a few of its higher-crime areas affect its national reputation. Some other drawbacks include high parking fees, high gas and sales taxes, and cold winters. Milwaukee, Wisconsin Milwaukee ranks fourth on the quality-of-life scale with a score of 54. It offers its residents easy access to the Great Lakes' scenic areas and beaches, historic breweries, and unique attractions such as the Harley-Davidson Museum. It also has plenty of walkable historical districts. With its cost-of-living score of 87, Milwaukee is more affordable than St. Paul (79), Minneapolis (74), and Chicago (74). However, many of Milwaukee's houses are older and require more investment in repairs than houses in other Midwestern cities. And like the residents of those other three cities, Milwaukeeans need to cope with long, frigid winters. Should you take a closer look at the Midwest cities? That weather makes the Midwest much less appealing than sunny Florida or California. Still, retirees looking for a good balance of lower living costs and higher living standards should take a closer look at St. Paul, Minneapolis, Chicago, and Milwaukee. They might not be as appealing as Fort Lauderdale or San Diego, but their advantages could outweigh their drawbacks.Read NextFeb 27, 2026 •By Kailey Hagen, CFPHere's How Much the Average Tax Refund Could Be Worth by RetirementFeb 27, 2026 •By Reuben Gregg BrewerDreaming of a Car-Lite Retirement?

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