There are lots of options on where to stay in Chicago. A hotel was out of the question. I wanted to feel like I live in Chicago, so having a kitchen and a real living space was non-negotiable. In addition, I would be working remotely, so a strong internet connection and workspace were also required.
There are multiple neighborhoods, each with its own charms, pros and cons. Originally, I looked at Lincoln Park. The one acquaintance I had in the city (friend of a friend) lived there and it was a nice, upscale area. There was appeal to living in an actual home - some cute little brownstone of some sort. It would give me a great feel for what it would be to actually live there. Then there was downtown... being in the heart of all the activity, with close access to museums and an abundance of theaters, restaurants etc. River North and Gold Coast have great residential areas with great restaurants and nightlife. Tons of other areas are a bit farther out, but completely accessible with Chicago's great mass transit.
I went to craiglist and searched vacation homes. Listings led me to additional sites that listed longer term rentals. You can rent anything from a room in a home to a full 10 bedroom house. Corporate housing services are also a good bet. After three solid days of searching and sending out inquiries, I stumbled across an amazing deal through http://www.leadingapartments.com/. They offered a one bedroom in the beautiful Aqua building, located between Millennium Park and the River. The rate was hard to beat ($130/day with no additional taxes/fees) and the location was outstanding. Booked!
Turned out to be better than I thought. The building is stunning and the views from my 36th floor unit were amazing. Lake Michigan on one side and Millennium Park (with Cloud Gate and Art Institute beyond) on the other:
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