In 2004, George Bush trounced John Kerry in Indiana by a larger margin than Kerry won Illinois by. Four years later, under very specific circumstances and in a Democratic wave year, Indiana flipped blue for the first time in 44 years.
The last time Illinois went Republican was in 1988. Before that, it voted Republican in the prior 5 elections. What circumstances would it take for a GOP upset win in Illinois, similar to Obama's win in Indiana?
A realignment.
Illinois and Indiana are former bellwethers. Ind. was a former bellwether during the first few decades of the Republicans competing in presidential elections. From 1856 to 1996, Ill. backed all winners except in 1884, 1916, 1976, each Democratic victories in which Ill. carried for losing Republicans. George Bush underperformed in 1988 Ill. and it easily flipped for Bill Clinton who, likewise, flipped out of the White House Bush with Election 1992. The state was moving heavily toward the Democrats that George Will noted in an article he wrote just before that year's election. It's a state, like neighboring Kentucky and its neighbor Tennessee, which eventually found one of two parties more reliable for its politics; therefore it is no longer competitive.
The Republican party's No. 1 problem is … the party.