I am a fashion stylist here in Chicago, and i have a swimwear shoot this Sunday, but i havnt found a location yet. I wanted to do an outside shoot by a pool, but i havnt found any places in chicago with an outside pool! Any ideas?

try the links in this thread.

Mid west/east studio resource thread.
https://www.modelmayhem.com/posts.php?thread_id=49830

Some of those sites might have pool/hotel listings but not likely for free.

i was going to say...try and contact a hotel, you may have to book a room and if thats a case go to a motel....they are usually cheaper

The Pennisula (at Superior and Mich Ave) has a really nice pool on the 19th floor.  Especally great at night with spectacular view of downtown.  I'd have no idea what this might cost, but contact their spa's frontdesk manager.  They offer day passes ($20 ?), maybe you could work something out.
Nika