Condo vs Apartment in Chicago: Property Tax Eats the Returns
Updated 20 May 2026
Chicago has the lowest entry price of any tier-1 US city, with median condos around $360K. That headline number hides the second-highest effective property tax in the country (roughly 2.1%) and a triennial reassessment cycle that can produce surprise step-ups. Here is how the buy-vs-rent maths actually play out, and which neighbourhoods make ownership work despite the tax burden.
Chicago snapshot (May 2026)
- Median condo sale price: around $360K (CAR market data, Q1 2026)
- Median rent (1BR): around $2,200 (Apartment List, April 2026)
- Effective property tax: roughly 2.1% in Chicago city limits (Tax Foundation)
- Median HOA: $400 to $700/mo mid-rise, $700 to $1,400/mo high-rise
- Typical break-even: 6 to 9 years (longer than national average due to tax drag)
Monthly comparison: $360K Chicago condo vs $2,200 rental
| Cost line | Buy | Rent |
|---|---|---|
| Mortgage P&I (30-yr, 7.0%, 20% down) | $1,916 | - |
| HOA fees (median Chicago mid-rise) | $550 | - |
| Property tax (~2.1% of $360K) | $630 | - |
| HO-6 insurance | $50 | - |
| Rent (median Chicago 1BR) | - | $2,200 |
| Renter's insurance | - | $18 |
| Total monthly outflow | $3,146 | $2,218 |
Sources: Cook County Assessor, Tax Foundation 2025 effective-rate rankings, CAR market data, Freddie Mac PMMS rate average. SALT cap of $10,000 limits federal tax deduction value for high-end buyers.
The Cook County reassessment cycle (the thing realtors do not lead with)
Cook County reassesses property values on a triennial cycle: city of Chicago in 2024, north suburbs in 2025, south suburbs in 2026. A reassessment can move your assessed value 15% to 40% in a single cycle, which flows directly into a property-tax increase the following year. Two consequences for buyers:
- Budget for a ~15% property-tax cushion year 1 to year 3 of ownership.
- The Property Tax Appeal Board (PTAB) and Cook County Board of Review accept appeals every cycle. Roughly 40% of filed appeals win some reduction; an attorney typically takes 33% of year-one savings as fee.
- Senior, homestead, and longtime-occupant exemptions stack. New buyers do not get longtime-occupant; first-year tax bills often run 10% to 20% higher than the previous owner paid.
Source: Cook County Assessor (cookcountyassessor.com), Illinois PTAB rules.
Other city comparisons
Related: 10-year calculator · HOA impact · Mortgage interest deduction