Cholo Magazine Interview #3: Annie Wonsey


A few years back, Annie Wonsey started renting out rooms in the Englewood house her grandmother had left her to travelers looking for cheap accommodations. Now, she is one of the most popular AirBNB spots in Chicago and has hosted people from all over the world—all in a so-called “dangerous” neighborhood. But the guests  are undeterred. 


CHOLO: What gave you the idea to turn your house into an AirBNB hotspot?

ANNIE: I saw AirBNB ads [on Craigslist]. It was an ad in New York that got my attention. The NY apartment was horrendous. BUT she had 15 recommendations!  I was like WOW, 15 folks stayed at this nasty place??? I knew I could get at least ONE person a month. But who would come to Englewood? Within 2 hours of posting, I had 8 confirmed bookings. Within 24 hours, I had bookings for 3 months! Within 2 weeks… I couldn’t get rid of folks. At many points, I was sleeping on the treadmill!

What sorts of things are in Englewood that people can visit?

Absolutely nothing! LOL.  It has been a HUGE improvement over the past years and there continue to be more. The only thing around these parts would be Harold’s Chicken and a lounge that stays packed on weekends.  That’s within walking distance.  But if you take a short ride, you can reach, as I call it, “Obamaland.”

What is the most common thing people say about Englewood when they come and stay with you?

You would think after over 600 guests, I wouldn’t get the same question: “Is it safe to walk around?” As long as you don’t do nothing stupid like pull out a $500 cell phone, sure. I’m not going to lie, Englewood has its problems. I’ve been here maybe 4 years and only heard shooting about 3 times. I repeatedly have the conversation about safety issues.  My guests have been robbed.  But [usually] not in Englewood.

What do the neighbors think?

I never met my neighbors until recently.  They would direct my guests [to the house] when they looked lost. One guest commented that an old lady on the next block said, “Hey baby, you goin the right way.  The white people go to the house on the next block.” When the white cops brought home three of my guests from the corner to my house, (with 20 other cops, see YouTube video: “White cops don’t want white guests in Englewood”), that was a game changer. One [man] from Louisiana came out with his glass of wine and [told the cops], “We’ve been here almost a month and the neighbors has been GREAT to us.  The only people we have a problem with is you cops.  I can’t walk down the street without being looked over by you all.” After that, I had my GUEST introduce me to my neighbors. He had been buying drinks and chillin out with many of the guests on the block.


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