Stays for 16+ guests in Chicago, IL
Stays for 16+ guests in Chicago, IL. Book direct on each manager's site, no OTA fee.
Find stays in Chicago, IL
Or narrow it with the fields below. Every one is optional and an empty field is not a filter.
Other facets here
Stays, best documented first
Designer Combo Loft 2E & 2W|Gold Coast/River North
Loft · 6 bed · 5 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Designer Penthouse Combo West | Gold Coast
Apartment · 6 bed · 4 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Designer Penthouse Combo | NW | Gold Coast
Apartment · 6 bed · 4 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Designer Penthouse Combo |North| Gold Coast
Apartment · 6 bed · 4 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Designer Penthouse Combo |South| Gold Coast
Apartment · 6 bed · 4 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Designer Penthouse Loft | Sleeps 20
Loft · 4 bed · 3 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Fulton Market Penthouse Amazing City Views
Apartment · 4 bed · 4.5 bath · sleeps 16
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Loft Collection 1, 2, 3
Loft · 9 bed · 9 bath · sleeps 42
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Loft Collection COMBO 01/02 | Terrace
Loft · 6 bed · 6 bath · sleeps 22
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
Loft · 6 bed · 6 bath · sleeps 22
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Loft Collection COMBO 02/03 | Terrace
Loft · 6 bed · 6 bath · sleeps 22
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Loft Collection COMBO 902/903 Terrace
Loft · 6 bed · 6 bath · sleeps 20
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Penthouse COMBO 07/02 Terrace | River North
Apartment · 5 bed · 5 bath · sleeps 16
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Penthouse COMBO 07/04 Terrace | River North
Apartment · 4 bed · 4.5 bath · sleeps 16
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Penthouse Loft - Heart of Fulton Market
Loft · 5 bed · 3 bath · sleeps 16
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Luxury Two-Level Townhouse | Patio | Lincoln Park
Townhome · 6 bed · 4 bath · sleeps 16
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
Unique Luxury Fulton Market Penthouse - Sleeps 32
Apartment · 9 bed · 7.5 bath · sleeps 32
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Rentals Chicago
How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-31 01:43 UTC. Prices and facts are whatever the manager published on their own site.