What is the median home price in Chicago?

The median home price in Chicago, IL is currently in the $325k – $385k range (data as of 2026-04). For fix-and-flip investors, distressed acquisition typically runs 65–80% of median, depending on submarket and condition.

What is a good cap rate in Chicago?

Stabilized rental cap rates in Chicago, IL typically fall in the 5.5% – 8.0% range as of 2026-04. Higher cap rates are common in older / B-tier submarkets, lower in A-tier neighborhoods with strong appreciation.

What is the average days on market in Chicago?

Days on market in Chicago, IL currently runs 42 – 60 days (data as of 2026-04). Faster DOM favors Fix & Flip exits; slower DOM (60+ days) usually pushes operators toward BRRRR or rental hold.

What is the average rent in Chicago?

Median rent in Chicago, IL is $1,800 – $2,250 / mo as of 2026-04. The most relevant rental benchmark for BRRRR is the 1% rule (monthly rent ≥ 1% of all-in cost) — verify against submarket-specific rent comps before underwriting.

Market · IL · 2026 data

Fix and Flip in Chicago, IL

Deep two-flat / three-flat stock; multi-unit-conversion friendly.

Chicago market thesis

Chicago has one of the deepest two-flat and three-flat inventories of any US metro. Multi-Unit Conversion and Multi-Unit BRRRR are the dominant strategies. The trade-off: high property tax burden (Cook County), older stock complexity, and a regulatory environment slower than Sunbelt peers.

Key metrics

$325k – $385k

Median home price

DealIntel · 2026-04

$1,800 – $2,250 / mo

Median rent

DealIntel · 2026-04

42 – 60 days

Days on market (median)

DealIntel · 2026-04

5.5% – 8.0%

Stabilized cap rate range

DealIntel · 2026-04

$60 – $115

Typical rehab cost / sqft

DealIntel · 2026-04

+10% to +18%

5-year appreciation

DealIntel · 2026-04

-0.3% / yr

Population growth (annual)

BLS · 2026-04

Top investor neighborhoods in Chicago

Logan SquarePremium two-flat flip
AvondaleMid-rehab BRRRR
Humboldt ParkSub-$350k two-flat entry
PilsenGentrification path
BridgeportStable B-tier BRRRR

Best strategies for Chicago

Of DealIntel's six underwritten strategies, the following rank best-fit-first for Chicago, IL. Every property in the platform is scored against all six paths in parallel; these are the ones that consistently produce the highest risk-adjusted return in this market.

Tailwinds — what's working in Chicago

United, Boeing, Citadel + healthcare + financial services
Deep two-flat / three-flat inventory unique to Chicago
Recent ADU pilot expansion (city-wide rollout in progress)

Kill flags — common ways Chicago deals fail

Cook County property tax burden (2-3% effective rate)
Older two-flat stock with knob-and-tube, asbestos, lead
Lake-effect winter + freeze-thaw cycle on masonry
Slow Chicago permit timelines (8-16 weeks)

DealIntel's 25-point kill list catches these and 20+ others on every property — see the platform overview for how the kill list runs before strategy evaluation begins.

ADU and multi-unit regulation in Chicago

Chicago ADU ordinance (2021) permitted in pilot zones; city-wide rollout phased through 2025-2026. Multi-flat zoning is the default in much of pre-1942 inventory — verify zoning district.

For state-by-state ADU and middle-housing regulatory background, see the ADU strategy guide and the multi-unit conversion guide.

Underwrite a deal in this market

Run a free ARV, MAO, or BRRRR calculation on a Chicago property using the calculators below. For full kill-list + six-strategy evaluation + Investment Memorandum PDF, see pricing — pay-per-deal from $149.

ARV calculatorConfidence-weighted comp method MAO (70% rule) calculatorMaximum allowable offer math BRRRR calculatorFull Buy-Rehab-Rent-Refi-Repeat model Cap rate calculatorNOI / value with asset-class ranges

Nearby markets and related guides

Written by

Matt Abadi

Founder, DealIntel

Matt Abadi is the founder of DealIntel. He leads the development of the platform's six-strategy underwriting engine, 25-point Kill List, and Monte-Carlo financial model — the institutional analysis stack DealIntel applies to every fix and flip deal. DealIntel was founded in 2025 with the central thesis that knowing when not to invest is the most valuable number on the page.

Last reviewed: 2026-04