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Gambling

Tax and bookkeeping guidance for gambling winnings, losses, and gaming-adjacent small businesses under IRS and state rules

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Chicago's Amusement Tax in 2026: What Venues, Streamers, and Ticket Sellers Must Collect

Chicago's amusement tax runs on three tracks in 2026 — 9% on live admissions, 10.25% on streaming and paid TV, 3% on registered ticket resales — plus a new 10.25% sports wagering tax and a $0.50 per-user monthly social media levy above 100,000 Chicago consumers. Here are the rates, the limits of the 1,500-seat exemption, the $100,000 remote-seller safe harbor, and the filing deadlines that trigger assessments.

mike

tax-compliancetaxsmall-business

When Your Nonprofit's Bingo Night Owes the IRS: UBIT, the Volunteer and Bingo Exceptions, and W-2G

The IRS treats charity gaming as an unrelated business, so raffle and bingo profits can owe UBIT on Form 990-T even when every dollar funds programs. Two exceptions usually save the event — substantially-all-volunteer labor and traditional bingo (never pull-tabs) — while raffles paying $600-plus at 300 times the wager trigger Form W-2G, with 24 percent withholding above $5,000.

mike

nonprofitgamblingtax-compliance

North Carolina Raised Its Sports Betting Tax to 23%: What Betting-Adjacent Small Businesses Must Track Now

North Carolina's 2026 budget raised the sportsbook tax from 18% to 23% of gross wagering revenue, added a 6% prediction-market tax effective January 1, 2027, and requires operators to report every bettor who wins more than $2,000 a year. Here is what bars, affiliates, vendors, employers, and bettors in the state need to record, reconcile, and calendar.

mike

gamblingtaxtax-compliance
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