Chicago, IL
Equity Comp in Chicago
Discover, McDonald's, Caterpillar RSU programs; pre-IPO planning for Chicago tech (Tempus, GTCR portfolio).
Why Equity Comp planning is different in Chicago
Chicago is midwestern financial and commerce hub anchored by the futures markets and fortune 500 headquarters. The combination of Financial services, futures markets, manufacturing, tech, healthcare. Major insurance and consulting presence. shapes how residents approach equity comp — including which tax levers apply, how state rules layer onto federal treatment, and where the highest-yield planning opportunities sit.
Chicago at a glance
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Population
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Median household
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Home ownership
$0K
Median home
Notable neighborhoods
Lincoln Park · Lakeview · Gold Coast · River North · Streeterville · Wicker Park · Bucktown · Hyde Park · Lincoln Square · Evanston · Wilmette · Winnetka · Highland Park · Naperville
Local landmarks
Willis Tower · CME Group · Chicago Board of Trade · Magnificent Mile · Wrigley Field · Navy Pier
Local challenges this content addresses
- Illinois flat 4.95% income tax + Cook County property tax
- Manufacturing-business succession planning
- Illinois estate tax exemption only $4M (vs federal $13.99M)
What equity comp planning covers
- RSU sell-at-vest vs. hold modeling with concentration-risk analysis
- ISO/AMT exposure calculations and exercise-timing strategy
- ESPP qualifying-disposition vs. ordinary-income tax-impact analysis
- 83(b) election decision support for early-stage employees
- 10b5-1 plan structure and trading-window guidance
Decision-stage resources
Model the numbers for your situation:
Chicago starter kit
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