Chicago is… my kind of town · Countdown to October

Before Chicago

The trip of a lifetime deserves a little homework. This page is just getting started — a growing stash of reads, facts, and history we'll keep piling on as the countdown to Chicago ticks along. New drops between now and October, so bookmark it and check back often.

These three readings are highly recommended before we land — together they give us the overview we need going into the trip, tracing a throughline from Kansas City's own Country Club District to Chicago's South Side to Chicago's rise as a national capital of architecture and ambition. Check back as we add more! Each one changes what you'll notice on the ground.

Play · Book Edition · 1959 01

A Raisin in the Sun

A Black family on Chicago's South Side decides what to do with a life-insurance payout — and runs headlong into a housing market built to keep them out of the neighborhood they choose. It became the first play by a Black woman produced on Broadway.

Why it's here

The story isn't invented. Hansberry's own father bought a home in a white South Side neighborhood in 1937 in defiance of a racially restrictive covenant, and fought the resulting lawsuit — Hansberry v. Lee — all the way to the U.S. Supreme Court, winning in 1940. It's the most human way into Chicago's housing history before you spend three days looking at its skyline.

History · Kansas City 02

J.C. Nichols and the Shaping of Kansas City

The definitive history of J.C. Nichols, who built the Country Club District and the Country Club Plaza using what he called "planning for permanence": strict lot sizes, mandatory homeowners associations, and deed-recorded racial covenants that barred Black and Jewish families from ownership. The model was praised nationally and copied in cities from Dallas to Beverly Hills — and Nichols' own leadership at the Urban Land Institute and the National Association of Real Estate Boards helped push similar covenant practices into federal housing policy, laying groundwork for the redlining maps of the 1930s.

Why it's here

Redlining can feel like something that happened to other cities, somewhere else. This is home turf — and once we're standing in Chicago, we'll see the very same playbook again, just written in a different hand.

Book · 2013 03

The Third Coast: When Chicago Built the American Dream

An immersive cultural history of Chicago in the decades after World War II — when the city sat at the literal crossroads of the country and its architects, broadcasters, writers, and politicians set out to define what modern American life would look like. Mies van der Rohe's glass towers, the birth of television as an art form, and the civic ambition (and hubris) that shaped the built city you'll be walking through.

Why it's here

It's the origin story for a lot of what's on the Explore Chicago tab — the skyline, the Loop, the sense that this city was built to prove something. Good context before three days of benchmarking against it.

Note: An Apple Books edition of the Worley title wasn't found at time of writing — it's an academic press book (University of Missouri Press), most readily available in paperback or through the library links above.