“Poor Chicago,” a friend of mine recently said. Given the number of urban apocalypses here, I couldn’t tell which problem she was referring to. Was it the Cubs never winning? The abominable weather? Meter parking costing more than anywhere else in America — up to $6.50 an hour — with the money flowing to a private company, thanks to the ex-mayor Richard M. Daley’s shortsighted 2008 deal? Or was it the fact that in 2012, of the largest American cities, Chicago had the second-highest murder rate and the ­second-highest combined sales tax, as well as the ninth-highest metro foreclosure rate in the country? That it’s the third-most racially segregated city and is located in the state with the most underfunded public-employee pension debt? Was my friend talking about how a real estate investor bought The Chicago Tribune and drove it into bankruptcy? Or how 15-year-old Hadiya Pendleton, who performed at the festivities for Barack Obama’s inauguration, was shot dead near the president’s Kenwood home?

Actually, “poor” seems kind. And yet even as the catastrophes pile up, Chicago never ceases to boast about itself. The Magnificent Mile! Fabulous architecture! The MacArthur Foundation! According to The Tribune, Chicago is “America’s hottest theater city”; the mayor’s office touts new taxi ordinances as “huge improvements.” The mayor likes brags that could be read as indictments too, announcing the success of sting operations busting a variety of thugs and grifters.

The swagger has bugged me since I moved here from New York 13 years ago. So I was interested to learn in “Chicago by Day and Night: The Pleasure Seeker’s Guide to the Paris of America” — a new annotated Northwestern University Press edition of an 1892 guidebook — that it initially surfaced in the era of wild growth after the Great Fire of 1871. In their 1909 plan, Daniel Burnham and Edward Bennett predicted that by 1950, Chicago would house 13.5 million people.

Today, Chicago has fallen short of such dreams. The city’s population, for example, is currently at 2.7 million, having dropped since a high of 3.6 million in 1950. But the bloviating roars on, as if hot air could prevent Chicago from turning into Detroit.