I’ve been following the City of Chicago’s regulatory battle with Airbnb closely in recent months, not from my normal Better Government Association watchdog perch but because bed and breakfast is personal for the Shaw family.  

And it’s top of mind on a holiday weekend filled with travel and lodging decisions.

Thirty-plus years ago, when I was a TV news reporter and we were raising our daughters in Old Town, my wife bought a bed and breakfast reservation service, and for the next decade she was a broker —connecting Chicago hosts who wanted short-term guests with visitors who found tastefully furnished single-owner homes or apartments preferable to cookie-cutter hotel rooms.

Our garden apartment was a B&B, so we met visitors who, with a few unpleasant exceptions, were courteous, well educated, and interested in discussing politics and culture, so conversations were enjoyable and informative—even for the girls.

In the ‘90s we went “all in”—converting a Lincoln Park property into a bed and breakfast inn, which we ran for a dozen years.

We had a few zoning and licensing spats with the city—that’s another story—but overall those were good years, as thousands of interesting guests from all over the world slept in our guest rooms and wandered into our dining area for breakfast.

It was a lively 24/7 home business that expanded our universe and helped pay college tuition bills. 

We eventually decided to slow down and decommission the inn, but a few years later an Airbnb-type flap erupted over the bad behavior of a few weekend renters in the small Michigan beach community where we own a home.

A few nights of excessive noise and rude behavior sparked a “no rental” movement that divided friends and neighbors, sparking a mini-war that was eventually resolved with rental limits and hard feelings among the permanent homeowners.

That experience, and a few bad actors that passed through our B&B doors over the years, makes it easy to understand why the recent Chicago battle is so intense and emotional.

Neighborhood residents don’t want homes and apartments on their block turned into “frat houses” filled with all-night revelers, but rental income is important for struggling property owners.

And unlike our low-tech era, the high-speed internet that makes it super-easy for travelers to digitally book an Airbnb, and hosts to operate one, is also inherently impersonal, which invites problems, including limited screening of hosts and guests, and a proliferation of short-term rentals in hot areas.

Those concerns precipitated a flurry of contentious City Hall hearings, protests and threats from Airbnb before the Emanuel administration finally hammered out a complicated compromise ordinance that doesn’t satisfy everyone but does address the main concerns. 

It taxes rentals, imposes a licensing fee on Airbnb, sets rules for renters, controls density, creates a searchable database of hosts, and gives residents a vehicle for confronting problems.

Some aldermen call it a good compromise, others say it’s not enough—that multi-billion dollar giant Airbnb got off way too easy—but we won’t be able to vet the claims until we see how the ordinance is implemented and enforced over the next year.

I’ll be watching, and I expect to experience, as Yogi Berra put it, “déjà vu all over again,” at least from a distance, as a new generation of visitors and renters reports on many of the same bed and breakfast experiences—good, bad and ugly—the Shaw family knows very, very well.