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The Buckingham ("The Buck") and Arc at Old Colony are a couple options I'd recommend. They do summer housing specifically designed for interns, so most other interns in your class will likely be staying in one of them. They are great because 1) they do short term rentals (10 week/2 month), 2) they are very close to where you'll be working and 3) you'll be surrounded by tons of other people doing the same thing as you (i.e., other interns) vs. being surrounded by people years older than you. The one downside is that they are located in the loop, which is not a great location for nightlife, but it's an easy Uber/L ride to get to River North/Old Town/LP/etc. I'm not sure on pricing, but your stipend should at least cover a chunk of it, assuming you have a roommate or two.

Definitely start looking as soon as you know you are going to be in Chicago because they book up fast once people start receiving offers

 

Stay at the Buckingham. Cheap and all the interns stay there

 

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