Chicago, IL vs Oakland, CA: Housing Market Comparison (2026)

Side-by-side Alpha Scores, affordability, momentum, supply, jobs, and rental yield · scores computed September 2026

Chicago, IL vs Oakland, CA side by side

Metric● Chicago, IL● Oakland, CA
Alpha Score4617
Price Momentum8321
Inventory Health——
Affordability343
Economic Strength2139
Rental Yield442
Median Sale Price$399K$932K
Price-to-Income4.47.3
Payment-to-Income26.8%44.0%
Months of Supply32
Gross Rental Yield4.4%3.0%
Overvaluation Index5050

Highlighted = the stronger read for that metric (supply, valuation, and payment burden are better when lower). Income/rent inputs lag annually.

How Chicago, IL and Oakland, CA compare, dimension by dimension

  • Affordability: Chicago, IL leads — Chicago, IL 34/100 vs Oakland, CA 3/100.
  • Price Momentum: Chicago, IL leads — Chicago, IL 83/100 vs Oakland, CA 21/100.
  • Economic Strength: Oakland, CA leads — Chicago, IL 21/100 vs Oakland, CA 39/100.
  • Rental Yield: Chicago, IL leads — Chicago, IL 44/100 vs Oakland, CA 2/100.

Frequently asked questions

Which has a higher Alpha Score, Chicago, IL or Oakland, CA?

Chicago, IL scores higher — 46 vs 17 out of 100. The Alpha Score is a 0-100 composite of price momentum, inventory health, affordability, economic strength, and rental yield.

Is Chicago, IL or Oakland, CA more affordable?

Chicago, IL is more affordable on our affordability dimension. Price-to-income is 4.4 in Chicago, IL and 7.3 in Oakland, CA.

Which housing market has stronger momentum, Chicago, IL or Oakland, CA?

Chicago, IL has stronger price momentum — 83/100 vs 21/100.

What is the median home price in Chicago, IL vs Oakland, CA?

The median sale price is $399K in Chicago, IL and $932K in Oakland, CA.

Want to swap in other cities, change the metrics, or chart the trend over time? Customize this comparison → in the interactive Compare tool. Or read the Chicago, IL market brief and the Oakland, CA brief.