The pope is on the final leg of his Latin American tour. The visit to Cuba comes 14 years after John Paul II's historic visit.
Moments after his plane touched down in Santiago, Cuba's second largest city, Pope Benedict blessed a group of children.
The pontiff is on a mission to renew the faith in Latin America's least Catholic country. Less than 10 percent of Cubans are practicing Catholics.
Cuba's communist government never outlawed religion, but it expelled priests and closed religious schools after Fidel Castro's takeover in 1959.
Unlike Chicago which has made a concerted effort to rid the city of its gangland history, the Chicago Outfit is part of the city's fabric in Havana.
Just 90 miles from the tip of Florida, American mobsters began using Cuba as their headquarters for offshore rackets in the early 1920s running rum, loan-sharking, prostitution and gambling and eventually the mob's initial cocaine trade.
During the late 1920s and 30s, the Hotel Sevilla Biltmore, close to Cuba's presidential palace, was a home away from home for Chicago mob boss Al Capone, whose pictures still adorn the lobby and who to this day has a suite named for him tucked away at the end of a 6th floor labyrinth. It is marked by a plaque citing Capone as an "Italian American famous gangster."
By the 1940s, every major Havana hotel and casino had been claimed by either the Chicago Outfit or New York's mafia families. It was a blueprint for later expansion to Las Vegas.
"Members of organized crime bribed Cuban government to allow them to have free reign in building and running very successfully the gambling enterprise in Cuba," said Arthur Lurigio of Loyola University.
Havana's majestic Hotel Nacional, which is the Vatican press headquarters for Pope Benedict's visit, was the site for one of the most famous summits in American gangland history.
In December of 1946, the hotel was closed to the public for a conclave of U.S. mob bosses so they could divvy up their illicit Cuban businesses.
Anthony "Joe Batters" Accardo led the Chicago delegation in meetings with notorious New York hoodlums Meyer Lansky and Lucky Luciano.
That Havana summit paved the way for Accardo's successor Sam "Mooney' Giancana to corner a sizable piece of Cuban business for the Chicago Outfit in the 1950s, building a hotel overlooking Havana Bay. The Riviera resort and casino became a favorite retreat for Chicago mobsters and the Hollywood glitterati.
For organized crime, it all came crashing down in 1959 when Fidel Castro overthrew an American-friendly regime that had also been in the mob's pocket.
"There is proof, documented proof that Sam Giancana, Johnny Riseli and others participated in several plots to have Castro assassinated," said Prof. Lurigio.
In Havana, the pope will have a private meeting with Raul Castro. The question is, will Fidel Castro be there as well?
Hugo Chavez, the president of Venezuela, has been brought to Cuba over the weekend for treatment for his cancer. Some speculate Chavez could also meet with the people.