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Updated over 2 years ago,
Airbnb 50%+ income! My strategy
I have a 4 unit in Rogers Park/Edgewater boarder by Clark and Devon and have been finding a lot of success with airbnb. Normally the unit rents for $1300 its a small 2br thats roughly 500 sqft which I rehabbed with modern finishes quartz, in unit laundry etc. when bought building unit was only at $600 a month. I also put up some cool artwork and modern furniture. List of supplies/costs... $1500 for the leather couch, $60 for small print out artwork and $200 for the large hand painted artwork over couch, bedframes I got from a startup called Thuma which is solid wood high quality easy to put together yourself for $995 each compared to $1500+ at stores for comparable quality, I highly recomend Thuma and no they don't pay me to say this haha.
Below is the calendar with 81.25% occupancy. I do this by setting days to $159 and then once mostly booked I change the little gaps to be at $99 with just a 2 day minimum. The $99 gap days sometimes fill within an hour of me editing the price. It's a nice strategy that seems to be working well. This is my personal unit I put on airbnb when traveling on extended vacations. I have also tested in winter and that season is less profitible but still nets around $1500 a month average which is above current rents, in winter I set rents lower at $119 and often get longer term guests.
Finishes...
One thing to note is don't believe the low airbnb comps you may see when checking the app. Most places around me are lower price but with being very responsive to inquires, positive reviews and in unit laundry, etc. the place still fills up at higher rates. I think the in unit laundry is a big plus and definitely worth installing.
The process for getting the airbnb licensed with city of Chicago was very easy. Paid I believe it was $125 and within 2 weeks had an email back saying approved with the license number. There was no inspection or any hoops to really jump through.
Feel free to reach out with any questions. Next I want to try an airbnb in the trendier neighborhoods such as Pilsen, Logan Square, etc.