Under the towering stone gaze of Cuban patriarch Jose Marti, the pope will celebrate mass for the masses in Revolution Plaza in Havana.
Unlike Pope John Paul II's Mass in the plaza in 1998, this is what Pope Benedict's view will be from the altar: dead, iconic revolutionaries Che Guevara on the left and on the right Camilo Cienfuegos, who is quoted from the grave as telling Fidel Castro: "you're doing a good job."
Behind the altar, the headquarters of the Communist Party, out of view, but like the government control of all things here, omnipresent.
"A lot of the things are state controlled, but otherwise, I don't feel that much," said Tinley Park resident Ron Centanni. "I've been in a Communist country before, many years ago, and I don't get that same feeling here."
Despite the continuing U.S. trade embargo, groups of Chicagoans have resumed coming to Cuba under the Obama Administration's newly-relaxed travel policy.
In Havana, they find a city frozen in time, where old American cars are driven as new, old buildings are where most everyone lives and an old political system called Communism continues to undermine U.S. relations.
Among the metro Chicagoans here now are groups on papal pilgrimages and others, including a pair from the DuPage County Bar Association on a research mission meeting with Cuban attorneys.
"I've bumped into a lot of Americans here and everybody seems to be having good experiences, different experiences," said Howard London of Highland Park. "I think it's always good for Americans to be able to go to countries, foreign countries, especially ones that have been off limits to us."
On Sunday, Las Damas De Blanco -- ladies in white -- protested the continued imprisonment of Cuban dissidents. At last week's protest, they were beaten and arrested by Cuban authorities but Sunday, in view of western media, police were hands off.
"We always are afraid, because we are just 22 women, but of course, you face your own fear" Mercedes Castillo said through a translator.
Cuban dictator Raul Castro will meet the Pope's plane Monday afternoon in Santiago and then meet privately with the Pontiff on Tuesday in Havana.
Still unknown is whether his older brother Fidel will meet with this Pope as he did with John Paul II in 1998.
In 1999, then-Illinois Gov. George Ryan met with Fidel Castro during a state agricultural mission. The trip landed Ryan in the Hall of Fame here at Havana's Nacional Hotel, a picture of the now-jailed Ryan, positioned right above Nicaragua's strongman President Daniel Ortega.