Some point to Obama's focus on gun violence and gun control laws when discussing the wave of murders in the city, but add that he is missing one of the core factors behind Chicago's descent into lawlessness and death.
"If the main topic with the president is only going to be gun control, we are pushing ourselves backward," one community organizer bluntly told CNN last month.
"What we need to do is address the root of the problem, the economic violence on a lot of these kids who don't have jobs or an education ..." she said.
Chicago's steep economic decline is certainly a factor. The city is overtaxed. Its inefficient, overweight government is drowning in political patronage, corruption and bureaucracy. But the larger social problem cries out for no-holds-barred law enforcement, putting criminals behind bars, taking control of the streets and making its neighborhoods safe again.
The role model for that kind of change was seen in the 1990s under New York City Mayor Rudy Giuliani, a tough, confident, no-nonsense former criminal prosecutor who cleaned up the streets, put the bad guys in jail and made Manhattan livable again.
When Giuliani became mayor in January 1994, the city was losing on average about 1,700 private-sector jobs a week. The homicide rate had soared to more than 2,000 a year, and more than a million New Yorkers were on welfare.
"The city was, in the oft-used word of the day, ungovernable. Unsalvageable. The economy was a wreck. Nothing the city did seemed to work. Social indicators were uniformly bleak. In 1993, for the first time, a majority of births in the city were delivered to unmarried mothers," wrote Michael Tomasky in New York magazine.
By the end of Giuliani's first year in office, the crime rate had plunged by 12 percent; it dropped by 16 percent in 1995 and 16 percent again in 1996.
Annual homicides, which had skyrocketed to 2,262 in 1992, fell well below 1,000 for the first time in decades in 1996.
Giuliani put more cops on the street, cut budgets and taxes, slashed welfare rolls, improved the schools, and showed he could not be pushed around by the unions.
There's little, if any, difference between the problems that confronted Giuliani and those that now face Rahm Emanuel in Chicago. But there's a big difference between the way they approached them.
Giuliani was a reformer who came into office to shake City Hall by its liberal lapels and end years of dysfunctional Democratic policies that fundamentally changed the way New York was run.
Rahm, a lifelong pol, is no reformer. His party has run and owned Chicago's City Hall for as long as anyone can remember (since 1931), and it remains a one-party, Democratic-encrusted fiefdom to this day, resistant to needed political and operational changes.
The result is a crime-ridden city that is rapidly decaying inside and out, economically, socially and politically. And it is likely to get worse in the years to come.
It's too bad we can't send Rudy Giuliani to Chicago, like the paladins of old, to clean up the town, put its economy back on track, and go after the bad guys with both guns blazing. If he were asked, I think he'd take the job in a New York minute.