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I would take a look at Old Town on the near north side. It's has the proximity to downtown attractions (Mich Ave, lakefront, etc) that Federal Hill does in Baltimore, is made up of walk-up style residences, and contains or borders a number of nice walkable stretches of small shops and restaurants. Old Town is a very established area, so you won't be able to bargain hunt if that's what you were after. You should have plenty of housing options on two professional salaries, but you may still find true single-family homes out of reach in this area (Chicago is not a row-house city - most walkups have multiple flats). As a long gentrified area, you'll find plenty of other young professionals among your neighbors. Unfortunately, you won't find anything like the actual hill in Chicago. Lots of places have roof decks with spectacular skyline views, and the lakefront offers great vistas, but Chicago is much flatter geographically than most of the East coast in general.
Alternatives:
- if you want more offbeat areas, look to Wicker Park/Bucktown west of the highway. Decent mix of professionals and a creative crowd, but has gotten more gentrified recently and is kind of cut off from the lakefront.
- Lincoln Park and Lakeview are other upscale areas that hug the lakefront. Pretty easy to find info on them here.
- South Loop has seen an explosion of condo development if you're looking for a high-rise lifestyle with very quick access to downtown.
- Lincoln Square/Rogers Park are less upscale but well established neighborhoods further north and west in the city that have seen a boom of interest in the last few years. You'd want to research a specific spot in those areas, but they're far from war zones.
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