In this Dec. 10, 2007, file photo, former newspaper baron Conrad Black leaves the federal building in Chicago after being sentenced to 6½ years in prison for fraud. (Jerry Lai/Associated Press)

A hearing to determine Conrad Black's bail conditions will be held Wednesday morning in Chicago, meaning the former media baron will soon be able to leave the Florida jail where he has spent the last 28 months.

The bail conditions U.S. District Court Judge Amy St. Eve chooses to impose will determine where Black, who won't be at the hearing, according to his lawyer, Miguel Estrada, goes next.

St. Eve is the judge who presided over Black's trial in 2007 and sentenced him to 6½ years in prison after a jury found him guilty of three counts of fraud and one count of obstruction of justice.

It's not clear where Black will go once he's released on bail. The National Post, quoting "sources familiar with the process," said Black is expected to ask that he be allowed to return to his home in Toronto.

But it would be unusual for Black to be allowed to leave the U.S. while on bail.

'I'd be very surprised to see the judge let him leave the United States, particularly given the conditions of his prior bail.'— Eric Sussman, former lead prosecutor in Black trial

"I'd be very surprised to see the judge let him leave the United States, particularly given the conditions of his prior bail," said Eric Sussman, the former lead prosecutor in the Black trial.

Sussman told CBC News he expects Black's passport will remain in the court's possession. Black could also be ordered to post a hefty bond.

While Black renounced his Canadian citizenship to accept a peerage in the British House of Lords, he was a Canadian resident at the time of his arrest and still owns a heavily mortgaged mansion in Toronto.

When Black was on bail before his conviction, he was restricted to Chicago, where the trial was being held, and Palm Beach, Fla., where he owned an oceanfront residence.

But reports last March said Black transferred the deed of the Florida home to a Connecticut-based investment firm — Blackfield Holdings LLC — to settle an $11.6-million US mortgage. It's not clear whether the current owners would let him stay there.

Black has also sold his posh homes in Manhattan and London.

Black may never return to prison

One former U.S. federal prosecutor says it's possible Black will never have to return to jail.

"Bail relates in many respects to the likelihood of success, and I think on some level, the court is adopting the view that if all that survives is the obstruction of justice conviction, then Conrad Black might be set free," Jacob Frenkel told the Associated Press.

One thing is clear. Black's legal problems are far from over, even if his prison days are largely behind him.

The U.S. Internal Revenue Service is seeking $71 million US in back taxes from Black, who also faces several civil suits from disgruntled shareholders of the Hollinger newspaper chain he used to head.

On Monday, the U.S. Court of Appeals for the 7th Circuit granted Black bail after the U.S. Supreme Court last month weakened the "honest services" law on which prosecutors relied to convict Black of mail fraud.

The high court ruled that the honest services law should not have been used in Black's case since it didn't relate to allegations of bribery or kickbacks. The judges then referred the case back to the lower court, which could uphold Black's convictions, acquit him or grant him a new trial.

The 2007 fraud convictions related to the jury's finding that Black improperly diverted $6.1 million US that should have gone to Hollinger shareholders. The jury acquitted Black of nine other charges.

With files from The Canadian Press and The Associated Press