Become a Mob Boss.
Take Over 1920s Chicago.

No. ChicagoShadows is free to play, and the game is decided on the streets — strategy, timing, and the alliances you build. You can't buy your way past a smarter boss.

It doesn't, much. ChicagoShadows is built by one person and costs nothing to play. If the city's given you a good night, you can buy the dev a coffee — it keeps the servers on and buys you nothing in the game. No perks, no edge, no head start.

As little or as much as you like. Because the world runs on a real clock, you can check in for five minutes to give orders and let your crew work — or sink into a long session plotting a war. Energy and income tick on their own; you don't have to babysit it.

Nothing. It runs in your browser. Make an account and you're in the city in seconds — or take a look around a live city first, no signup needed.

It keeps going. There's no timer wiping the board — your territory, treasury, and reputation persist, and the world moves on while you're away. It's one continuous, living Chicago, not a round that wipes every week. A city ends only when one boss wins it (see below).

A city runs continuously until one mafia boss comes out on top — on a territory city by holding 60% of its businesses for 7 unbroken in-game days, on a money city by banking $1,000,000 first. Then the city closes as a chapter of Chicago history with a crowned victor. There's no clock counting down to a reset; a city ends only when someone earns the win. And you're never waiting on it: new cities are opening all the time, so there's always a fresh Chicago to walk into and a near-conclusion one to fight for the crown in.

No — and that's the point. Different cities run on different in-game clocks. Some move fast, where days pass in hours and an empire rises and falls in a weekend; others run slow and deliberate, a long campaign you grind out over weeks. It's up to you what kind of experience you want — pick a city whose pace matches how you like to play, or run a crew in more than one at once.

It is. The original round-based game still runs at turns.chicagoshadows.com — fixed seasons, a clean slate every round. This site is the continuous version: no rounds, and a city runs until someone wins it. The two run separately, so you’ll need an account here.

No. The city's always mid-game — but it's built for new arrivals. You start with your own turf and crew, the map is full of unclaimed and weakly-held rackets to take, and reputation is earned by playing smart, not by who showed up first. Veterans have history; you have fresh ambition and nothing to lose.