Suing a city
Although I'm not certain because this isn't my legal domain, my hunch is that the city would be protected under sovereign immunity, which is a doctrine precluding the institution of a suit against the sovereign [government] without its consent. Though commonly believed to be rooted in English law, it is actually rooted in the inherent nature of power and the ability of those who hold power to shield themselves.
In England it was predicated on the concept that "the sovereign can do no wrong", a concept developed and enforced by - guess who? However, since the American revolution explictedly rejected this interesting idea, the American rulers had to come up with another rationale to protect their power. One they came up with is that the "sovereign is exempt from suit [on the] practical ground that there can be no legal right against the authority that makes the law on which the right depends." 205 U.S. 349, 353.
"tatutes waiving the sovereign immunity of the United States must be`construed strictly in favor of the sovereign." McMahon v. United States, 342 U.S. 25, 27 (1951).
11 U.S.C. S 106, "Waiver of Sovereign Immunity," provides:
(a) A governmental unit is deemed to have waived sovereign immunity with respect to any claim against such governmental unit that is property of the estate and that arose out of the same transaction or occurrence out of which such governmental unit's claim arose.
The interest served by federal sovereign immunity (the United States' freedom from paying damages without Congressional consent)
Federal sovereign immunity is readily distinguishable from the states' immunity under the Eleventh Amendment and foreign governments' immunity under the Foreign Sovereign Immunities Act. The latter two doctrines allow one sovereign entity the right to avoid, altogether, being subjected to litigation in another sovereign's courts. Pullman Constr., 23 F.3d at 1169. Similar sovereignty concerns are not implicated by the maintenance of suit against the United States in federal court. Federal sovereign immunity has had such broad exceptions carved out of it that, as Pullman Construction concluded, "Congress, on behalf of the United States, has surrendered any comparable right not to be a litigant in its own courts." Id. In the present day, federal sovereign immunity serves merely to channel litigation into the appropriate avenue for redress, ensuring that "No Money shall be drawn from the Treasury, but in Consequence of Appropriations made by Law." Pullman Constr. at 1168 (quoting Art. I, section 9, cl. 7).
Federal sovereign immunity is a defense to liability rather than a right to be free from trial.
The Supreme Court has ruled that in a case involving the government's sovereign immunity the statute in question must be strictly construed in favor of the sovereign and may not be enlarged beyond the waiver its language expressly requires. See United States v. Nordic Village, Inc., 503 U.S. 30, 33-35 (1992).
Each state and city has it's own laws and immunity statutes. I'm not familiar with Illinois nor Chicago.
On another note, while it may be a waste of time and money, it may be worth suing on the grounds that the state has stripped him of his FEDERAL Constitutional rights to keep and bear arms and attempt to gain some national exposure. Where state and federal laws conflict, federal laws generally preempt state laws. I believe it's the "Doctrine of Supremecy" which states that where Federal laws and state laws conflict, Federal laws preempt. States can only GIVE citizens MORE rights, but cannot take Federal rights away. The real problem is that there is no federal right to carry a concealed weapon, that law is reserved to the states individually.
However, it would be an interesting suit. I considered that exact same thing in Colorado before we were a shall issue state, but I would not have had standing to sue (you have to have a personal reason to sue like being harmed, not the anticipation of being harmed) because I had not been robbed. Here, your friend has standing to sue. Maybe he can find a good pro-gun Illinois lawyer to do it pro bono in hopes of national attention and changing the laws.
