Chicago - IL vs Orlando - FL: 2026 Housing Comparison

What this means for buyers

Orlando - FL is roughly 8% more expensive than Chicago - IL in typical home value. Homes sit on market longer in Orlando - FL (41 days vs 14), suggesting more buyer leverage there.

Chicago vs Orlando: what the numbers say

At today's 7.40% average 30-year rate with 20% down, the typical home would cost about $1,970 a month in principal and interest in Chicago and $2,123 in Orlando, a gap of $153 a month.

Typical rent runs $2,163 in Chicago and $1,929 in Orlando, so the mortgage payment alone is 0.9 times rent in Chicago and 1.1 times rent in Orlando, before taxes and insurance.

Home prices are 13.7 years of rent in Chicago and 16.6 in Orlando; the lower ratio in Chicago means buying there is cheaper relative to renting.

Over the last 23 months typical values moved +8.3% in Chicago and -5.6% in Orlando; over just the last three months the change was +1.5% in Chicago and -0.3% in Orlando.

Homes sell for 100.5% of list price in Chicago and 97.3% in Orlando, after 14 and 41 days on the market, with price cuts on 28% and 28% of listings. All three signs point the same way: buyers have more room to negotiate in Orlando.

The number of homes for sale is up 1% on a year ago in Chicago and down 3% on a year ago in Orlando.

Payments assume a 30-year fixed loan at the Freddie Mac weekly average rate (2026-10-15), 20% down, principal and interest only. Home values, rents and market figures are Zillow Research metro data.