Short term rentals Chicago

[Daisy Ruiz]

Hey everyone, 

Has anyone done short term rentals in Chicago. I have been reading thier seems to be a lot of rules and regulations. Does anyone have any pointers? 

Thank you in advance 

[Michael Baum]

Hey @Daisy Ruiz, choose another area.  That is the best advice I can give you.

The forums have several folks that have gotten hosed by the city trying to do a STR even though they did everything right.

There are a lot of loopholes the city can use to keep people from doing a STR.

For example, an up/down duplex. Live in one and STR the other. Meets the standard of living onsite...but not according to the city.

[Paul De Luca]

@Daisy Ruiz

To echo @Michael Baum, I have not seen or heard from many people operating STRs in Chicago. Not saying it can't be done but you have to know the regulations. More often, I see people in Chicago using the MTR strategy to side step the STR regulations.

I've considered buying a SFH with an in-law arrangement in Chicago to use as an STR because to me that seems like the best way to employ the strategy.

[Jonathan Klemm]

Hey @Daisy Ruiz - I owned and operated a short term rental here in Chicago for the last 7 years.  I finally decided to close the doors mainly because the unit used was not available anymore, but also because the regulations got stricker and stricker over time.

Now, if you want to use your 2-4 as an STR, you need to show proof that you are living in the unit you are renting by sharing a government-issued ID with that exact unit or your tax exemption form.

If you have a building over 5 units, it's a bit easier but still challenging ( you can rent up to 25% of the units out for airbnb)...the few people I know that are successful are NOT the owners of the building, but more so the operator of the airbnb unit aka str arbitrage

[Garrett Brown]

According to the data, I would skip Chicago for STR and go to Peoria or Antioch. I have not heard many success stories in Chicago. I had one guy at BPCON24 tell me he was crushing it there, but I have no verification besides his word, and I was shocked.

[Andy Nathan]

Yes, Chicago has strict regulations for short-term rentals, including mandatory registration and zoning restrictions. Be sure to check local rules and your building's status before proceeding to avoid fines or penalties. What has been your biggest concern about navigating these regulations?

[Victor So]

Quote from @Daisy Ruiz:

Hey everyone, 

Has anyone done short term rentals in Chicago. I have been reading thier seems to be a lot of rules and regulations. Does anyone have any pointers? 

Thank you in advance 

 Short answer - if you’re looking to rent rooms in the house or unit you live in, go for it. It can be fairly profitable in that it could help you live for free, etc. If you’re looking to scale, then it can be very difficult. I have friends who own properties with 5+ units who Airbnb 1-2 units in those buildings but again there are limits to the scalability thing. There’s other creative ways to make it work. For example, I have a partner who lives in a single family home we own together. He applied for the license under his name since he lives there and I basically run the Airbnb operations. We make it work because we an agreement but could I do similar things with other properties I have and scale? Not sure.