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5 Bedroom Stunning Penthouse with Private Rooftop

Casey User Profile

5 Bedroom Stunning Penthouse with Private Rooftop

16+ guests
5 bedrooms
8 beds
4 baths
16+ guests
5 bedrooms
8 beds
4 baths
Self check-inEasily check yourself in with the keypad.
Quick responses17 recent guests said this host responded quickly.
Great communication100% of recent guests gave this host a 5-star rating for communication.

This has been the preferred Chicago property of Airbnb founder and CEO, Brian Chesky.

Located in the beautiful and historic Old Town neighborhood in the heart of downtown Chicago. On bustling Wells Street, steps to all the great things Chicago has to offer - the lake, Topo Gigio and Old Town Ale House (both Anthony Bourdain favorites), high-end boutiques, and the famous Second City Comedy Club.


Indoor fireplace
Cable TV
Laptop friendly workspace

Sleeping arrangements

Bedroom 1
1 king bed
Bedroom 2
3 single beds
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed, 1 couch
Common spaces
1 single bed, 3 couches, 3 air mattresses

House Rules

No smoking
Check-in is anytime after 3PM
Check out by 11AM
Self check-in with keypad


39 Reviews

Anand User Profile
July 2018
Amazing all around! The perfect location in the middle of everything and Casey is very accommodating.
Jackie User Profile
July 2018
Amazing central location in Old Town, super stylish space and plenty of room for a large number of guests. We would love to stay at Casey’s place again the next time we visit Chicago.
Kristen User Profile
July 2018
Casey's place is out of this world . We we rented it out for 9 people on our team and our annual team meeting and it was superb. Not only is the place immaculate, but it is so tastefully decorated and provides anything that you may need. The entry is so convenient and location id…
Amy User Profile
July 2018
Casey's property in Old Town is great for a large group! We had 14 people, consisting of family, and the space was perfect for us! We had everything needed for our visit and were all very comfortable in this homey apartment. The location is great - within walking distance to l…
Jared User Profile
July 2018
Amazing loft in a great location in Old Town! Tons of amenities and the host was very responsive! Would highly recommend for a large group. Rooftop and grill a great perk!
Joshua User Profile
July 2018
We had a large group and some small children for a young adult extended wedding / family reunion. (Ages 1-40s). 2 levels was nice for our group. Was quiet on middle level when kids sleeping. Upper level has deck and pool table. Really cool place. Was a great location for us. Too…
Krista User Profile
June 2018
Casey’s place is wonderful! My fellow guests were blown away by the whole space. Fun setting for a mid-sized group!

Hosted by Casey

Chicago, Illinois, United StatesJoined in March 2013
Casey User Profile
174 Reviews
Casey is a SuperhostSuperhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
Love to explore
Response rate: 100%
Response time: within an hour
Always communicate through AirbnbTo protect your payment, never transfer money or communicate outside of the Airbnb website or app.

The neighborhood

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