Among the proposed ordinances the Chicago City Council could consider Wednesday is one that would help the city collect its 4.5 percent hotel accommodations tax on vacation rentals made through online room-sharing services.

Similarly to how ride-sharing platforms Uber and Lyft match car drivers with passengers as an alternative to taxis, Airbnb acts as a digital clearinghouse to host traveling guests in short-term rentals in apartments or homes.

Since 2010, the cash-strapped city has required vacation rental businesses to be licensed and pay hotel accommodation taxes.

The proposed change would expand the tax-collecting duty to any party that collects the rental charges, including Airbnb and similar sites.

If passed, the ordinance would help fill city coffers. But while the policy might legitimize Airbnb’s operations with the city, issues would still remain with condominium and apartment associations that are opposed to unwanted overnight visitors in their buildings.

David Sugar, a partner at Arnstein & Lehr LLP, co-chairs his firm’s condominium law group. He said that’s often the case.

“Most condominium associations strictly prohibit any sort of short-term lease or arrangement,” he said.

But the service still remains attractive in a town with high living costs. The arrangement is appealing to consumers, Sugar said, as people can rent fully furnished luxury high-rises for less than a small downtown hotel room.

“The problem with these Airbnb arrangements is they’re almost undetectable by the condominium association,” he said.

When room-sharing first started to gain popularity, building tenants would leave keys at the front desk for their guests.

“Now, when buildings are focusing on them, the handoff of the keys is done outside the building so nobody knows,” Sugar said. “I would almost describe it as a promise-of-security issue.”

The associations and neighbors don’t have any records of who is accessing and staying in the buildings, he said. Acknowledging the practice with an association board would tip members off to a likely rules violation.

That, in turn, prevents hosts from getting licenses from the city. The licenses go for $500 per unit and regulate safety and insurance requirements. They require affidavits from an association representative attesting that vacation rentals are allowed.

“There’s all sorts of requirements,” he said, “and one of them … is you cannot get a city of Chicago vacation rental license without the approval of your condo board — which no condo board in its right mind would give.”

Sugar said his clients are increasingly aware of Airbnb and are patrolling listings looking for photos from their buildings, identified by the view out the window or by decor.

Often, hosts will post under alias names and won’t put the exact address of the building online.

“When we catch somebody, in about two minutes, they pull their posting,” Sugar said.

Condos haven’t enacted new rules specifically to target Airbnb rentals, he said, because the practice fits under long-standing prohibitions on short-term rentals. Many agreements allow for fines equal to the short-term rental price and allow buildings to block illegal occupants from entering.

“The trick is, how do you catch them?” he said.

For its part, California-based Airbnb leaves enforcement as an issue between hosts, their associations and city hall.

In an statement, an Airbnb spokeswoman said hosts must certify they will comply with local rules before listing their space.

The company also provides a page for hosts to visit outlining local laws and advises them to check their leases and building rules. Its Chicago page provides links to information on vacation rental and bed-and-breakfast licensing in the city code.

A city Law Department spokesman referred questions about license enforcement to the city’s Department of Business Affairs and Consumer Protection.

A BACP spokeswoman did not respond to questions about enforcement by press time.

The ordinance, sponsored by Mayor Rahm Emanuel, passed the Finance Committee on Nov. 10, and the full City Council deferred voting until a later meeting. The next meeting is set for 10 a.m. Wednesday at city hall.