With the opening of the Obama Presidential Center, its leaders have long touted the potential tourism benefits the new building will bring to Chicago’s South Side, even encouraging residents to rent out rooms and homes over short-term rental platforms like Airbnb.
Now, a WBEZ analysis of city data shows licenses for short-term rentals in the 20th Ward, which covers parts of several South Side neighborhoods including much of the Woodlawn community just west of the Obama Presidential Center, have increased sharply compared to the rest of Chicago.
WBEZ obtained data on housing units licensed for short-term rentals from the Chicago Department of Business Affairs and Consumer Protection (BACP) via the Illinois Freedom of Information Act. Comparing licenses expiring in 2019, the first full year of available data, with licenses expiring this year, WBEZ found the city, overall, has seen a 38% decrease in shared housing licenses. But the 20th Ward has seen a 46% increase during the same span.
As hosts open rooms and apartments to tourists coming to check out the Obama Presidential Center, some see a real opportunity. But others are worried that in neighborhoods that have historically been affordable, like Woodlawn, things are changing. Researchers say short-term rentals can deplete a neighborhood’s housing stock, pushing up prices and rents. Housing advocates and renters seeking to live in these neighborhoods say they are being priced out. Meanwhile, some advocates and lawmakers also say the city isn’t doing enough to enforce the laws that are meant to protect the housing supply.
Lots of Airbnbs
In February, as part of a series of “Community Tourism Prep Sessions,” the Obama Foundation held a workshop in partnership with Airbnb to help residents “earn extra income by sharing their homes with Obama Presidential Center visitors.”
Kristy Ramsey was not able to attend the virtual session, but she did not need the training.
An Airbnb “Superhost” with nearly 180 glowing reviews, Ramsey has been hosting guests in her three-bedroom Woodlawn condo for more than 10 years.
Ramsey says she usually makes around $60 per night, with guests paying close to $80 for cleaning and Airbnb fees. But with the Obama Presidential Center opening, she says Airbnb allowed her to raise her nightly rate by about $30. Ramsey says this month looks to be one of the busiest months she has had in all her years hosting an Airbnb.
“I think Obama Center may have something to do with it, but also June is the month that everything starts happening,” she says.
Ramsey says she uses Airbnb income to help pay for her groceries and mortgage. On good months, when she brings in between $1,200 to $1,800, she is even able to use funds to make car payments.
While she’s seen a lot of benefit from her own Airbnb, Ramsey does worry about how the proliferation of these kinds of rentals could affect the neighborhood. Over the dozen years she has lived in her condo, however, Ramsey says she has seen neighbors get displaced.
“It’s a double-edged sword for me,” Ramsey says. “You start to get better neighbors, the neighborhood looks better, but on the flip side, it hurts me to see people have to move or leave a home that they may have lived in for years and years, just because [rents] have increased and they can’t afford it.”
Higher Rents
Researchers say Airbnb listings contribute to higher rents and housing shortages.
Edward Kung, who has studied the impact of Airbnbs on housing across the country, said the theory is simple: “[Airbnbs] shift some of the housing stock away from residents to tourists, so you get a potential decline in the housing stock, and that would push up prices and rents.” said Kung, an economics professor at California State University, Northridge.
Kung’s 2019 study showed that a 1% increase in Airbnb listings leads to a 0.018% increase in rents and a 0.026% increase in house prices. He said those numbers are conservative, as they account for factors like gentrification and tourism demand, and also given the increase in real estate investors in the past decade.
He added that Airbnb’s year-over-year average growth was more than 44% at around the time of the study, which suggests that “Airbnb growth can explain something on the order of like one to three percentage points year over year of house price and rental rate growth, which is actually quite a lot.”
Airbnb representatives, however, say reining in short-term rentals “do not have a significant impact on housing availability or affordability.” They also said short-term rental restrictions don’t result in lower rents. An ordinance in New York City, Airbnb representatives said, resulted in a 92% drop in Airbnb listings across the city but “rents continue to break new records each month while vacancy rates remain unchanged.”
They tout the benefits of hosting in Chicago, claiming that South Side residents earned millions of dollars from hosting tourists in 2025.
Airbnb reps said the typical Chicago host earned about $20,000 last year through hosting. The company says a survey shows 60% of Chicago hosts say funds from hosting Airbnb helped them stay in their homes and manage the city’s rising cost of living. Company representatives did not answer questions about whether the homes of those surveyed were owner-occupied or used strictly for short-term rentals in investment properties.
The Obama Foundation did not respond to a list of questions, citing “limited bandwidth” related to the center’s opening.
Infiniti Gant, a housing organizer with Southside Together, said a lack of enforcement from the city has led to the proliferation of Airbnbs in the area. And now, she herself is experiencing the shortage of affordable housing firsthand.
Gant grew up in the Island Terrace Apartments, across the street from where the Obama Presidential Center now stands. For years, she has wanted to move back into the area.
“I want to come back,” she said. “I miss living here, and it’s hard to find a place that is affordable.”
She said she understands longtime residents who rent out part of their home on Airbnb to help pay the mortgage, which includes ever-increasing property taxes. But she takes issue with investors and companies that “have money and are making more money through Airbnbs. I am 100% against people building their wealth on the backs of others.”
WBEZ spoke to multiple Airbnb hosts who said they have flexible living arrangements that allow for leasing entire apartments and houses to short-term guests.
Gant made it clear she is “not against the Obama Center. We want people in the neighborhood to be able to benefit from the Obama Center. But if people [outside] see the Obama Center as a cash cow, then the people who are here are not going to be able to benefit.”
Investing in Airbnbs
Any units that hosts are looking to list on Airbnb require licensing by BACP in some capacity. The City has different criteria for the number of units someone can use as a short-term rental depending on the type of building. For example, for single-family homes and two- to four-unit buildings, the licensed host must dwell in the house or unit as a primary residence — which means at least 245 days in the calendar year — and can only operate one short-term rental. For buildings with five or more units, the license holder does not need to live in any of the units, and can have more short-term rentals in the building.
An Airbnb spokesperson says hosts must abide by city regulations in order to comply with the terms of service to use the platform. The company also says it “provides the city with the ability to remove non-compliant listings directly from our platform.”
The majority of the license holders within the areas around the Obama Presidential Center have only one short-term rental unit to their name. But some have much more — one licensee has 12 different properties registered under their name. And many listings on Airbnb feature rentals that are not owner-occupied.
A spokesperson for Mayor Brandon Johnson said in a statement that “the Johnson administration shares concerns on the impact Airbnbs and other supply pressures have on housing affordability” and has supported the Jackson Park Housing Pilot ordinance last year “to protect long-term residents of the area … who are facing gentrification and displacement.”
Ald. Desmon Yancy (5th) was one of the sponsors of that ordinance. He calls the practice of full-time, short-term rentals “exploitative.”
Yancy also says there are “bad actors” who skirt the city’s Shared Housing Ordinance related to residency requirements.
“I’ve used Airbnbs. I’m not against the concept,” he says. “But I always know the difference between an apartment that is strictly for short-term rental and one where somebody still has hair care products in the bathroom.”
Yancy says “it would be a shame if the monument to the first Black president, in the heart of this historic Black community, displaces Black residents. I don’t think that that is President Obama’s intention at all, but it is what the market is bearing.”
Ald. Jeanette Taylor (20th), whose ward has seen the amount of short-term rentals increase by 46% since 2019, agrees.
“For people who own their homes and are struggling — that’s who I want to have Airbnb,” she says.
Taylor also says it’s too early to tell if the Obama Center will bring the crowds it promised.
“It’s supposed to bring these 700,000 people a year,” Taylor says. “We’ll see.”
Whether the answer is yes or no, both Taylor and Yancy say it’s worth revisiting the Shared Housing Ordinance and evaluating whether it is working the way it should.
Jennifer Thomas, an Airbnb host in Woodlawn, is unsure if more regulations is the answer.
For her, buying a three-flat in Woodlawn last December is a way to help keep some longtime residents in place while enjoying her new Chicago neighborhood.
Thomas, a healthcare executive, wanted a place to call home when she took a new job in Chicago in 2024. She bought her building in late 2025 and has continued to lease out the first- and third-floor apartments to longtime renters.
“It was important for us as homeowners and landlords to preserve the people who’ve been in the community,” she says.
But because she travels 80% of the time, and her husband currently lives in Virginia, Thomas decided to turn the second-floor unit into an Airbnb when she is out of town. Her grown daughter also stays at the condo from time to time.
As for concerns that Airbnbs shrink the housing supply and increase rents, Thomas says “more conversations” need to be had between landlords and tenant groups.
“As a landlord, people assume that you’re wealthy, when honestly, what you’re trying to do is at least break even or not owe money every single year,” she says.
Thomas says one of her passions is providing memorable experiences for her guests.
With the Obama Presidential Center’s opening, she hopes her home will help visitors “spend time, energy and money in this area” and showcase the beauty of the neighborhood.