Straight Up Chicago Investor Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market
Dec 30, 2025
A conversation about why 2026 could be a strong year for Chicago real estate. They emphasize neighborhood-level data over sensational headlines. Discussion covers tight inventory, rising rents, tax and local rule risks in Cook County, and where to prioritize purchases like industrial and Class A single-family. Practical advice: know your numbers, stick to a niche, and act decisively.
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Local Knowledge Beats National Predictions
- Chicago investing is driven by hyper-local, street-by-street knowledge that outsiders on YouTube lack.
- Mark Ainley stresses that backyard expertise in neighborhoods and suburbs gives more reliable signals than broad national predictions.
Buy If You Find A Deal Because Inventory Is Tight
- If a buyer calls, Mark's short answer is buy now because inventory is extremely tight across the area.
- He cites examples like a large suburb with only 39 single-family homes on market to show scarcity is pushing values and rents up.
Prepare For Possible Cook County Tax Hikes
- Cook County sellers should expect assessment changes in 2026 that may raise taxes by about 20% in some western townships.
- Mark flags this as an area-specific risk buyers must account for when underwriting.