The Latin School of Chicago is one of the "Big Three" private K-12 schools in Chicago (Latin, Francis Parker, and University of Chicago Lab School) which are usually the last holdout before rich families flee for the greener grass and overfunded public school systems of the North Shore. As such, the pressure to have your kids accepted in one of the schools is immense, as their admission can mean the difference between remaining in the opulent and friendly confines of the Gold Coast or Lincoln Park and leaving the city. Kindergarten students at The Latin School of Chicago and Francis Parker (arch-rival of sorts) are accepted largely based upon their behavior in "Play Parties", social simulations designed to test how well the children will belong in the neurotically upper-crust environment of the school. Then and later on, potential increases to the school's gargantuan endowment are looked well upon, but later on in the years the school's admissions become more focused on merit. The token minority students generally show up around 9th grade, a product of Latin's highly successful "High Jump" program which gives inner-city students a chance at summer school and access to private schools and the promise of higher education.

The environment students enter into in at the Latin School is a very uniquely upper-crust and neurotic one. The school itself feels like an office building with its carpeted floors and white drywall, and the students have a certain corporate air as well. On the other side the school's students are famous for drug-and-sex-fueled debauchery. The school also has a tradition for excellence in soccer and water polo, and a jock culture intermingles with the trust fund culture of the general student body. Parties are frequent and wild, and get-togethers are always in session during the day at local restaurants on Wells Street (to eat in the cafeteria is a mark of shame or poverty, it seems). Thefts of hundreds of dollars or expensive iBooks are frequently reported; of course it is the nanny-raised, perpetually-starved-for-attention anorexic rich students who in the end are at fault. A pervasive attitude of spoiled abandon permeates the largely single-parent-businessman-raised students.

Academically, the Latin School is one of the finest high schools of its kind in the nation. Courses are rigorous and heavy writing abounds. Students are frequently accepted to top colleges in disproportionate amounts, and score very highly on SAT and AP tests in general (the school has its own SAT-like admission test).