Chicagoan Libertarianism is a kind of libertarian, economically moderately right to far-right, and culturally neutral but sometimes left-leaning political ideology.
It is used quite often to refer to 
Neoliberalism, although only a few economists of this school have referred to themselves as neoliberals.
It is quite a simple ideology, it's 
Libertarianism based on the thought of the Chicago School of Economics, which is a Neoclassical school of economics associated with the University of Chicago, mostly known for the Libertarian economist of second generation, and Nobel prize winner, Milton Friedman.
Within the precise ideas on economic believes, it is associated with the rejection of 
Keynesianism in favor of 
Monetarism (Which states that it's desirable to have a Monetary policy controlled by the government as long as it expands money supply consistent with GDP growth) until the mid-1970s when it turned to new classical macroeconomics strongly based on the concept of rational expectations. Specifically, 
Neo-Keynesian economics was developed as a response to new classical economics and Friedman's critiques to Keynesianism, electing to incorporate the idea of rational expectations without giving up the traditional Keynesian focus on imperfect competition and sticky wages.
Chicago economists have also left intellectual influence in other fields, notably in pioneering public choice theory and law and economics, which have led to revolutionary changes in the study of political sciences. The school also has some research done that has left some impact in fields as diverse as social economics and economic history. Thus, there is not a clear delineation of the Chicago school of economics, a term that is more commonly used in the popular media to refer to Friedmanite economics rather than being used in actual academic circles.
History
Personality and Behaviour
Chicago Libertarians behave as an average kind of moderate Libertarian economist.
How to Draw
ChicagoLib's design is a combination of the Chicagoan and Gadsden flags
- Draw a ball,
- Draw the flag of Chicago (2 horizontal light-blue (#C9F1FF) lines, with 2 red (#FF0000) stars between them',
- Draw a black (#141414) Gadsden snake,
- (Optional) Below the snake draw some variation of the words "Don't tread on me",
- Draw the eyes, and you're done!
Relationships
Friends
Hayekism - My more radical nephew who wants to end the FED.
Paleolibertarianism - A bit more traditional sibling.
Anarcho-Capitalism - A very extremist cousin.
Libertarianism - My father who's got almost the same beliefs as me.
Classical Liberalism - My moderate Grandpa.
Neoliberalism - My best known son.
Frienemies
Hoppeanism - While we somewhat agree economically they want to transgress the NAP against different kinds of people and give Libertarianism a bad name.
Austrolibertarianism - Completely rejecting empiricism as a way to measure the economy wasn't the right move, you should be more flexible like Hayekism.
Paleoconservatism - He used to be a cool guy back in the day, but now he's a protectionist that doesn't value free trade, also too way too statist.
Pinochetism - I've already said it but I'll say it again; I never advised Pinochet, I never endorsed Pinochet (however, there was a miracle in Chile's economy!).
Enemies
Social Democracy - They have corrupted the western societies with their inefficient bureaucracy and their welfare states.
Keynesianism - Way too Statist, and he doesn't even know the basics of economics.
National Socialism: - They want to treat people differently before law, and killed several millions of people.
Marxism–Leninism - Socialist and Authoritarian. No. Just no.
Further Information
Wikipedia
Literature