Destination 29

Destination 29

“Travel far enough, you meet yourself.”

― David Mitchell​

What is Destination 29?

Destination 29 is essentially a short term and vacation rental company, that prides itself on hospitality, cleanliness and unique experiences in unicorn properties. Come experience our unique short term rentals, through our vision. Find out more. 


Near all of Chicago’s must sees but surrounded by nature! 1937 Print Shop located between the Chicago River & Forest Preserves. With beautiful trails & amazing river walk paths, and close to every amenity, this is truly a home away from home.


Nestled within a 3.5 acre forest, this home is a historical relic from the brilliant mind of Michael McGuire, who studied under Frank Lloyd Wright. Built in 1972, and commonly referred to as the “Hobbit House.” Hobbits wish they could afford such luxury.​


Currently under renovation, this mid century modern home  rests on the edge of a beautiful, heavily wooded and well maintained 12 acre park. This stunning property features an in ground pool and a sauna. Available Spring 2023.

“Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.”

– Anthony Bourdain​