The 20th Ward, located just west of the Obama Presidential Center on Chicago’s South Side, is exploding with short-term rental licenses.
Overall, Chicago has seen a precipitous drop in housing that’s formally licensed for short-term rental units. Data obtained by WBEZ and cited by the Chicago Sun-Times shows a 38 percent drop Chicago-wide in short-term rentals. Bucking that trend however, the 20th Ward has seen a substantial increase to 46 percent.
The Obama Foundation has been advocating for an increase in Airbnb stock in the area, according to the outlet.
However, in historically affordable sections of the 20th Ward, like Woodlawn, residents say they’re being priced out of their homes. Several housing advocates say the city isn’t upholding their end of the deal to enforce housing supply protection, according to the publication. Housing researchers say that adding too many short-term rentals can drive up rents for entire neighborhoods.
The math is simple, according to Edward King, an Airbnb researcher who cited “conservative” figures to the publication. His study in 2019 showed that a 1 percent increase in Airbnb listings turns into a 0.018 percent increase in rents, nearly double for house prices.
Airbnb representatives cited by the outlet disagreed with portions of the contention. They said that the impact, while real, isn’t significant, and short-term rental restrictions don’t bring rents back down. According to the representatives, South Side Chicago residents earned millions from hosting tourists in short-term rentals, with the typical host earning $20,000 in 2025.
The Obama Presidential Center will formally open this month on Juneteenth. It will be years before analysts calculate if the short-term rental juice was worth the squeeze, or if the Center will even bring in the 700,000 people a year it’s meant to, the outlet reported.
The Obama Foundation declined to provide comment to the publication. A spokesperson for Mayor Brandon Johnson told the outlet that the administration has concerns on the impact of short-term rentals on affordability.
— Hunter Cooke
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