Chicago to Boston (Cambridge, Somerville, Brookline: apartments, to rent, townhouse)

[Smokey024]

I am thinking of making a change and transferring to Boston, but need some help figuring out what areas I should look at and if someone could relate these areas to parts of Chicago that would be awesome. I would be working downtown near the Financial District, so I would prefer using public transportation with a commute time of less than an hour. I am in my mid-20s and would like to keep rent as cheap as possible, but max would be about $1400 and I would like to be able to rent a house or townhouse since I have a dog. Thanks for any help.

[goyguy]

I have a sister and BIL who live in Chicago (Wicker Park now, previously Ukrainian Village.) Sis had apartments on North Dearborn, Oakdale, and Chestnut before she got married. Based on this...I think Boston's MBTA (aka "the T") has it all over the El. The only advantage the CTA can claim is that you can catch the Blue Line - at least the stretch from the Loop to O'Hare - at "all hours," while the T shuts down between 1 AM and 5 AM. Rapid-transit lines radiate from downtown in all directions, and the routes don't meander or form a U. Commuter rail is fairly comparable to Metra in that trains are available to towns as far as 50 or so miles from downtown. Bus tie-in's are also good. We don't have transit lines down the middle of any expressways, and no longer are there any elevated trains. Subway stations I've used in Chicago have always felt kind of foreboding, and Sis tells of sometimes waiting to get on an El (depending on the line) 'til she can see or hear that a K-9 patrol is on board. We don't have that level of apprehension on the T. Even before "Big Brother" cameras became a fact of life, people never hesitated before walking onto a platform or getting on a train, no matter if the platform was downstairs or upstairs from the token booth (and now the card readers and their associated machines.) It's not escaped my notice, though, that lone women are seldom seen on the subway after about 10 PM.
If you're looking for a "scene" neighborhood like Rush St or Lincoln Park, Boston's South End + Cambridge's Central, Porter, Inman, and Harvard Squares + Somerville's Davis and Union Squares + Brookline's Coolidge Corner and Brookline Village are the most similar. The flip side, logically enough, is that rents are on the steep side. More selection at or below your price point would be available in South Boston, Allston-Brighton (student ghetto), sections of Dorchester, Jamaica Plain, and Mission Hill (also student ghetto.) Each of these neighborhoods have plenty of places for going out, although you won't find "to-be-seen-in" spots or necessarily the latest in food/drink trends.
Finding a townhouse, let alone a free-standing dwelling, for as low as $1400/month might take some doing. You can probably find apartment guides online to aid in that quest. There are "townhome" complexes in all of the areas already mentioned, but I doubt any would come that cheap. Know, however, that Boston is home to the three-decker - a bay-windowed structure with one unit per floor and LOTS of space. Many if not most "three-decka" apartments are renting for more than the amount you're after, but should you not find one that you think would be affordable on your own the typical unit is so large that you can double or triple up on the rent with roommates and never feel crowded in. Landlords may not always be canine-friendly, but the prevailing trend around here is to charge a deposit or tack on a "pet fee" to the rent.
I could go on (and on) but will stop here 'til I find out how I can best assist. Feel free to send me a DM!