Every year, a significant number of Chicago suburb retirees make the move to Florida 55+ communities — Tampa, Sarasota, The Villages, Naples, Orlando. And every year, a meaningful fraction of them return to Illinois within 3–5 years. Understanding both the genuine advantages and the common disappointments is the foundation of making a good decision.
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Talk to a Specialist →The Financial Case for Florida
Florida has no state income tax — same as the effective result for Illinois retirees drawing retirement income (Illinois exempts retirement income, so both states produce $0 on your Social Security and pension). The meaningful Florida financial advantage is property taxes: Florida's homestead exemption and relatively low millage rates produce effective property tax rates of 0.8–1.2% on homesteaded properties, compared to Illinois's 2.0–2.8%. On a $380K home, Florida saves $4,000–6,000/year in property taxes vs. Illinois collar county rates.
The offset that has changed since 2022: Florida homeowners insurance. Premium increases of 30–100% in many Florida markets following Hurricane Ian, combined with carrier exits from the state, have produced insurance costs of $5,000–$12,000/year for many Florida homes that cost $1,500–$2,500 to insure in Illinois. Run current insurance quotes for the specific Florida market and zip code you are targeting. The property tax savings may be partially or fully consumed by the insurance premium.
What the Chicago Suburb Transplant Actually Finds in Florida
Florida 55+ communities — particularly The Villages, Sarasota's Palmer Ranch, and Tampa's Sun City Center — are in many ways more developed and amenity-rich than Chicago-area equivalents. The social infrastructure, the activity calendars, the recreation facilities are large-scale operations compared to the Chicago market's smaller communities. Chicago suburb buyers who made the transition and stayed overwhelmingly say the community social life was better than expected.
What surprises Illinois transplants: the heat. June–September in Florida involves temperatures and humidity that many Illinois retirees find genuinely oppressive — not just inconvenient. The winter is the product; the summer is the cost. Spend a July week in your target Florida market, not just a February one, before committing.
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Why Chicago Retirees Come Back
The pattern is consistent across the Nova55Living network: the Chicago suburb retirees who return within 5 years almost always cite the same factors in the same order. First: grandchildren and family proximity — the realization that missing the first years of grandchildren's lives, paying for flights and hotels to visit family, and not being available for family events was a larger sacrifice than anticipated. Second: social isolation in a new place — meeting people and building genuine friendships in a retirement community is possible but takes 2–3 years, and many returnees found the process harder than expected. Third: medical continuity — re-establishing relationships with cardiologists, oncologists, and specialists who know your history is genuinely difficult.
The Chicago suburb retirees who stay in Florida almost always report: their social network moved ahead of them (Illinois friends who made the move earlier), their family is geographically dispersed anyway (so Florida is no more distant than Illinois was), and they had genuinely committed to the climate preference rather than the tax savings as the primary motivation.
The Practical Advice
Rent for a year before buying. This is the single most commonly cited advice from Chicago retirees who made a successful permanent Florida move. Rent in your target community for a full 12 months — through a Florida summer, through snowbird season, through the off-season — before committing to a purchase. The communities that look like paradise in February look different in August. And renting gives you 12 months to build the social foundation that makes the permanent move sustainable.
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Talk to an AgentRelated: Illinois Retirement Income Tax Guide · IL vs. Arizona Tax Comparison · Chicago Metro 55+ Communities