Should I Airbnb or rent?

7 Replies

Would it make more sense to Airbnb a condo in a booming neighborhood in Chicago or rent it out?

Have you checked your condo docs to see if you can do short term rentals? A lot of condo associations don’t allow them.

Situational.  If I had more time than money and could do it, I would try Air Bnb.  I've never done it before but it appears to require more work (at least until you create systems) but have more potential monthly cash flow.  It would be like a second job, I imagine.  Not as passive as long-term rentals, I don't think.  Also you'll have to budget furnishing it.  Another cost not associated with most long-term rentals.  

Good luck,


It makes more scenes to have it as a conventional rental unless you are looking for a second job. Airbnb is a heck of a lot more work. Do you have the time.

Airbnb has more upfront costs, like furnishings. You will also have more ongoing costs because of maintenance, marketing, and management, but the 1.5-2x revenue will more than make up for the added costs. Time wise, if you hire a professional manager who takes care of scheduling, communication, and coordinating maintenance, I don’t think you’ll spend more time on a short-rental situation than on the long term rental after the initial set-up period.

In summer (due to tourism) AIR-BNB might bring you more money depending on the location.

When it starts to get colder you probably want to switch to more longer term rental, since its furnished more like corporate housing. 

If you have a condo association that allows for short term rentals in Chicago you are looking at a gold mine. Chicago is the 3rd largest metro area in the US so furnishing it would be dirt cheap using Offerup/FB marketplace. If you don't want to do do work then you would turn your place into a corporate rental. You get the short term rental money with the same work as a traditional long term rental. You would only use Airbnb during your vacancies. In this scenario you will be more than likely tripling or quadrupling your mortgage. 

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