Median rent is 17% lower in Chicago ($1,380/mo vs $1,653/mo). Buying is cheaper in Chicago, where the median home runs $315,200 versus $676,800. Households earn more in Winter Park ($98,076 vs $75,134 a year).
City A
Chicago, IL
City B
Winter Park, FL
How much would you need to earn in Winter Park, FL to maintain your standard of living from Chicago, IL?
A cost-of-living index isn't available for one of these cities yet, so we can't compute an equivalent salary.
Based on BEA Regional Price Parity (cost index) for each city's metro area. A rough estimate of overall purchasing power, not tax or take-home pay.
Metric
Chicago
Illinois
Winter Park
Florida
👥Population
💰Median Household Income
Annual
🏠Median Gross Rent
Per month
🏡Median Home Value
📊Cost of Living Index
US avg = 100
🔑1BR Fair Market Rent
HUD FMR
🔑2BR Fair Market Rent
HUD FMR
🔑3BR Fair Market Rent
HUD FMR
🌬️Air Quality Index
Lower = cleaner
🏛️Top State Income Tax
Top marginal rate
🧾State Sales Tax
Statewide base rate
🎂Median Age
Years
✓ = better value · Sources: US Census ACS, BEA RPP, HUD FMR, EPA AirNow, Tax Foundation
Median rent is modestly lower in Chicago at $1,380/mo compared to $1,653/mo in Winter Park (17% gap). Home buyers face a steeper market in Winter Park: the median home is $676,800 versus $315,200 in Chicago — 53% more expensive.
1BR Fair Market Rent
2BR Fair Market Rent
BLS OEWS 2023 — metro-level data
Florida has no state income tax, while Illinois tops out at 4.95% — giving Winter Park a clear advantage for high earners. Sales tax is 6.25% in Illinois and 6.00% in Florida; Winter Park has the lower rate (local add-ons may apply in both).
Chicago
Income tax: 4.95%
Sales tax: 6.25%
Winter Park
Income tax: None
Sales tax: 6.00%
Air quality data is available for Chicago (avg AQI 21.0) but not yet for Winter Park.
Pick Winter Park if you prioritize higher median household income ($98,076/yr).
Pick Chicago if you prioritize cheaper rent ($1,380/mo median).
Pick Winter Park if you prioritize no state income tax.
Is Chicago cheaper than Winter Park?
Cost of living index data is not yet available for one or both cities.
How much is rent in Chicago vs Winter Park?
Median rent is $1,380/mo in Chicago, IL and $1,653/mo in Winter Park, FL. Chicago, IL has the lower rent by about 17%.
Which has higher salaries — Chicago or Winter Park?
Median household income is $75,134 in Chicago, IL and $98,076 in Winter Park, FL. Winter Park, FL has the higher median income. Note that BLS occupational wages in the table above show wages for specific jobs.
Which city has better air quality?
Air quality data is not yet available for one or both cities.
Which has lower taxes — Chicago or Winter Park?
Florida has no state income tax. Illinois has a top rate of 4.95%.
What salary do I need in Winter Park to match my Chicago income?
RPP data needed for salary equivalence calculation is not yet available.
Data last updated: December 1, 2024 · Sources: US Census ACS, BEA RPP, BLS OEWS, HUD FMR, EPA AirNow, Tax Foundation · Methodology