Rosehill Cemetery

The entrance gate to Chicago’s largest cemetery is worth the trip alone. Designed by WW Boyington (the architect who created the old Water Tower on Michigan Ave), the entry looks like a cross between high Gothic and low Disney. Through the gates you’ll see the graves of plenty of Chicago bigwigs, from Chicago mayors and a US vice president to meat man Oscar Mayer. You’ll also find some of the weirdest grave monuments in the city, including a postal train and a huge carved boulder from a Civil War battlefield in Georgia. More than one ghost story started here; keep an eye out for vapors as night falls.