If you want an active night life scene near the financial district, try RIver North, West Loop or Gold Coast. The first two are walking distance to the Loop; the Gold Coast is maybe a 15 minute train ride down.
These neighborhoods are not cheap. If you are looking to rent...expect to pay about $1000 for a studio, $1500 1bd and so on. If you are looking to buy, depending on finishes, you would be pressed to find something you really want for less than $300k (small 1bd). Of course, there are bargains to be found, just depends on what you are willing to sacrifice.
I used to rent a 700 sq. ft. 1bd East of Michigan Ave. in Streeterville (sub-neighborhood of Gold Coast) for $1195, there we_re no amenities, window a/c_s, crap kitchen and not the best apartment...but the location was nice for the time I was working up there.
Hope this helps! I_ll check back soon!
Edit- my bad I read wrong, thought you were moving TO san diego! sorry!
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