14 Best Midwest Retirement Towns for the Upper Middle Class

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Upper-middle class households hunting for the ideal Midwest retirement spot may want to start their search in Illinois.

The Prairie State dominates a recent GOBankingRates list of the top locales for upper-middle class retirees. Of the 14 destinations that made GBR’s list, seven — including the top four — are found in Illinois.

The study evaluated retirement-friendly communities across the region using a blend of affordability metrics, livability scores and demographic indicators. Data was sourced from multiple outlets, including the U.S. Census, Sperling’s Best Places, AreaVibes, and Zillow. GBR used the Pew Research Center’s definition of upper middle class. The full methodology is included at the end of this story.

Illinois suburbs such as Wheaton, Arlington Heights, and Oak Park stand out for their balance of affordability and high livability. But the list also highlights strong contenders outside Illinois, including Upper Arlington in Ohio, Edina in Minnesota, and Leawood in Kansas — all of which offer high livability scores and robust retiree populations.

Key Findings

• Wheaton — located about 25 miles west of Chicago — ranks No. 1. Wheaton boasts a strong livability score (84) and a comfortable cost-of-living threshold of $121,798, one of the lowest on the list.
• Park Ridge posts the highest livability score among Illinois cities (86), paired with a comfortable cost of living of $131,629.
• Upper Arlington, Ohio, is the highest-ranked, non-Illinois city, boasting the highest livability score overall (90).
• Senior populations vary widely, from 17.3% in Oak Park to 24.6% in both Chesterfield, Missouri, and Glenview, Illinois.
• Livability scores range from strong to modest, with highs in Upper Arlington (90) and lows in Wildwood, Missouri (64) and Mequon, Wisconsin (69).

Read on for a breakdown by city.

1. Wheaton, Illinois

• Annual cost of living comfortably: $121,798
• Population 65+ (%): 17.4%
• Livability score: 84
• Single family average home value: $538,916
• Average monthly mortgage: $3,107

2. Arlington Heights, Illinois

• Annual cost of living comfortably: $121,682
• Population 65+ (%): 19.3%
• Livability score: 80
• Single family average home value: $541,936
• Average monthly mortgage: $3,125

3. Oak Park, Illinois

• Annual cost of living comfortably: $126,837
• Population 65+ (%): 17.3%
• Livability score: 83
• Single family average home value: $571,481
• Average monthly mortgage: $3,295

4. Park Ridge, Illinois

• Annual cost of living comfortably: $131,629
• Population 65+ (%): 20.1%
• Livability score: 86
• Single family average home value: $610,055
• Average monthly mortgage: $3,517

5. Upper Arlington, Ohio

• Annual cost of living comfortably: $138,744
• Population 65+ (%): 18.9%
• Livability score: 90
• Single family average home value: $687,463
• Average monthly mortgage: $3,964

6. Glen Ellyn, Illinois

• Annual cost of living comfortably: $131,560
• Population 65+ (%): 18.6%
• Livability score: 83
• Single family average home value: $605,296
• Average monthly mortgage: $3,490

7. Elmhurst, Illinois

• Annual cost of living comfortably: $135,013
• Population 65+ (%): 18.5%
• Livability score: 85
• Single family average home value: $631,934
• Average monthly mortgage: $3,644

8. Evanston, Illinois

• Annual cost of living comfortably: $139,457
• Population 65+ (%): 17.8%
• Livability score: 84
• Single family average home value: $667,987
• Average monthly mortgage: $3,851

9. Chesterfield, Missouri

• Annual cost of living comfortably: $127,353
• Population 65+ (%): 24.6%
• Livability score: 71
• Single family average home value: $598,836
• Average monthly mortgage: $3,453

10. Wildwood, Missouri

• Annual cost of living comfortably: $126,520
• Population 65+: 19.7%
• Livability score: 64
• Single family average home value: $586,167
• Average monthly mortgage: $3,380

11. Glenview, Illinois

• Annual cost of living comfortably: $151,145
• Population 65+: 24.6%
• Livability score: 78
• Single family average home value: $751,208
• Average monthly mortgage: $4,331

12. Edina, Minnesota

• Annual cost of living comfortably: 152,204
• Population 65+: 22.7
• Livability score: 79
• Single family average home value: $785,567
• Average monthly mortgage: $4,529

13. Mequon, Wisconsin

• Annual cost of living comfortably: $139,293
• Population 65+: 23%
• Livability score: 69
• Single family average home value: $669,603
• Average monthly mortgage: $3,861

14. Leawood, Kansas

• Annual cost of living comfortably: $152,948
• Population 65+: 22.2%
• Livability score: 74
• Single family average home value: $772,459
• Average monthly mortgage: $4,454

Methodology: For this study, GOBankingRates analyzed retirement towns from across the United States to find the best places for the upper middle class. Retirement towns are places with greater than the national average percentage of the population ages 65 and over, currently at 16.8%. Middle class is defined by Pew Research Center as two-thirds to double the median household income ($51,813 to $155,438). To find the upper-middle class, the middle-class income range is broken into thirds, with the upper third being the upper-middle class ($120,896 to $155,438). With the cities identified using data from the U.S. Census American Community Survey, the cost-of-living indexes were sourced from Sperling’s BestPlaces for each location. Using the cost-of-living indexes along with the national average expenditure costs for retirees, as sourced from the Bureau of Labor Statistics Consumer Expenditure Survey for Retired Consumer Units, the average expenditure cost for each location was calculated. The average home value was sourced from Zillow Home Value Index. Assuming a 10% down payment and using the national average 30-year fixed mortgage rate of 6.63%, sourced from the Federal Reserve Economic Data on Aug. 13, the average mortgage cost was calculated for each location. Using the average mortgage and expenditure costs, the total cost of living was calculated. Using the 50/30/20 finance rule that says that needs should not exceed 50% of household income, the total cost of living for necessities was doubled to find the comfortable cost of living. The locations with a comfortable cost of living within the upper-middle class income range were kept. The livability index was sourced from AreaVibes and used to determine the overall quality of life. Using the remaining retirement towns, the percentage of the population age 65 and over was scored and weighted at 0.50, the total cost of living for necessities was scored and weighed at 1.00, and the livability index was scored and weighted at 1.50. All scores were summed and sorted to find the best retirement towns for the upper-middle class. All data was collected on and is up to date as of Aug. 13, 2025.

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