I don’t know. Chicago could imitate the resorts in Jamaica. Have a bus meet the tourists/gamblers at the airport, Drive them to the walled, heavily-guarded resort/hotel/casino. Offer guarded trips from the resort to selected tourist attractions. At the end of their stay, they take the bus back to the airport. Because of the money involved, have CPD escort the bus to avoid incidents. Don’t know how this would help with the taxes though.
Have a bus meet the tourists/gamblers at the airport,
Wedged between Ohare field and Chiraq is the Rosemont Casiino.
Complimentary 24/7 round-trip daily Casino Shuttle service from the CTA Rosemont Blue Line Station. Validated transportation voucher from Rush Rewards required for return trip. https://www.riverscasino.com/desplaines