This district spans the lands of Cook and Lake Counties. Its story began with the 28th Congress on March 4, 1843. Its first champion was Stephen A. Douglas, whose Kansas–Nebraska Act sparked a chain of events that gave rise to the Republican Party itself.

The district's borders have shifted with time. Since the great redrawing of the 1990s, it has guarded most of Chicago's North Side. After the 2010 redistricting, its reach expanded west into DuPage County.

In the modern age, Democrat Rahm Emanuel held the seat from January 2003 until January 2, 2009, when he departed to serve as White House Chief of Staff. A special election followed on April 8, 2009, where Mike Quigley claimed victory and became the district's next guardian.

The Fifth is a fortress of Democratic power, bearing a Cook Partisan Voting Index of D+20. Save for four brief years, the district and its predecessors have remained under Democratic control since 1909.

Two of those years came after Dan Rostenkowski fell in the wake of the Congressional Post Office scandal, allowing Republican Michael Patrick Flanagan to seize the seat. The scandal echoed across the nation, helping ignite the Republican Revolution of 1994.

But the victory was short-lived. In 1996, State Representative Rod Blagojevich defeated Flanagan after a single term. Since then, no Republican challenger has claimed even 35% of the vote. In 2003, Blagojevich passed the mantle to Rahm Emanuel, continuing the district's long tradition.