Airbnb host Lenora Blackamore at her Airbnb in Woodlawn

The surge is likely due to overbooked downtown hotels and the lack of accommodations on the South Side, Breit says. As a result, guests from all over the world, but mostly the Midwest, are flooding into homes such as Lenora Blackamore’s Woodlawn unit.

Blackamore, a 47-year-old web developer who has lived in the neighborhood for 20 years, will host five Lollapalooza guests. Despite the festival’s raucous reputation, she says her young tenants have never caused issues in the past.