Community Adventures

Roaring Underworld: Chicago

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World

Chicago: Set in the Roaring Twenties (roughly 1920-1933), the world draws from real history: the 18th Amendment banned alcohol nationwide starting January 17, 1920, turning booze into a black-market goldmine. Will you play as a gangster? starting and growing your own criminal empire? speakeasies, bootlegging operations, and violent turf wars nothing is off limits. Will you join the police? fight for justice and the law, bring sanity and reason back to the Windy City by any means necessary. the choice is yours fluid allegiances, betrayals, and hybrid paths. Nothing’s off limits: bribery, assassinations, heists, or even starting a full-scale gang war. The world is dynamic, with events based on player actions, like rival gangs rising if you neglect territories or federal agents intervening if corruption spikes. Rise through ranks, build task forces, and aim to clean up Chicago—or flip to the dark side for power, money and glory.

Story

Players opting for the underworld start as low-level enforcers or bootleggers, climbing ranks through cunning and force. Inspired by real figures like Al Capone (who rose from Brooklyn roots to control Chicago’s bootlegging by the mid-1920s),your empire could involve: Bootlegging and Distribution, Speakeasies and Vice, Turf Wars and Alliances:Dark Paths: No limits means options like human trafficking ties, political assassinations, or even sparking events like the St. Valentine’s Day Massacre for narrative depth. On the law side, players begin as beat cops or detectives, working to dismantle empires amid widespread corruption (pre-Prohibition, more cops than politicians were tied to crime). Raids and Investigations, Corruption Mechanics: Tempt players with bribes; accept them to fund gear but risk exposure. Form “Untouchables”-style squads of honest cops, inspired by federal agents like Eliot Ness, Political Maneuvering:Edgy Options: include brutal interrogations, planting evidence, or vigilante justice against untouchable mobsters. Base the world on a stylized Chicago map, divided into gang territories (e.g., South Side for Capone’s Outfit, North Side for Irish gangs). Use procedural generation for hidden spots. Iconic areas: • The Loop (Downtown): Bustling hub for speakeasies like the Drake HotelSouth Side (Outfit Territory): Industrial zones for stills and warehouses. • North Side: Rival gang st • Dynamic Events: AI spawns pop-up raids, drive-bys, or speakeasy parties

With AI Game Master installed, launch this adventure by clicking here. If AI Game Master is not installed, you will be taken to the app store to download it.

Disclaimer: The monsters contained within this compendium are the result of generative AI processes, created without specific intent or design towards any existing intellectual property. Any resemblance to characters, creatures, or entities from Dungeons & Dragons (D&D), Pathfinder, Warhammer, and other RPGs (such as Star Wars RPG, Cyberpunk 2020, Shadowrun, Call of Cthulhu, World of Darkness), tabletop games, video games, literature, or any other media is entirely coincidental and unintended. This compendium is not affiliated with, endorsed, sponsored, or specifically approved by any company or publisher. Our aim is to explore the creative possibilities of AI and to provide unique and imaginative monsters for entertainment and inspiration.