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Chicago Area

8 stays in Chicago · 5+ bedrooms

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Beds:Any1+2+3+4+5+6+8+10+
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Modern Multi-Unit, Gym & Workspaces
from $884/night

Modern Multi-Unit, Gym & Workspaces

House

Chicago, Illinois

7 bed · 5 bath · sleeps 26

Gym, Game Room & Theater
from $381/night

Gym, Game Room & Theater

House

Chicago, Illinois

7 bed · 3 bath · sleeps 18

Game Room, Gym & Theater
from $332/night

Game Room, Gym & Theater

House

Chicago, Illinois

8 bed · 3 bath · sleeps 18

Near Lakefront + Red Line, Apt & Workspace
from $329/night

Near Lakefront + Red Line, Apt & Workspace

Apartment

Chicago, Illinois

6 bed · 2 bath · sleeps 12

Near Lakefront + Red Line, Apt & Workspace
from $3,000/night

Near Lakefront + Red Line, Apt & Workspace

Apartment

Chicago, Illinois

6 bed · 2 bath · sleeps 12

Walk to the Beach & Private Office
from $221/night

Walk to the Beach & Private Office

Apartment

Chicago, Illinois

5 bed · 2 bath · sleeps 13

Near Lake & Museum, Modern & Game Area
from $156/night

Near Lake & Museum, Modern & Game Area

House

Chicago, Illinois

5 bed · 3 bath · sleeps 12

Arcade, Theater, Gym & Office
from $336/night

Arcade, Theater, Gym & Office

House

Chicago, Illinois

7 bed · 3 bath · sleeps 15