Boston to Chicago or Washington DC, which is best (job, cheaper, move to)

[Allscot]

I live in Metrowest Boston and have similar job offers in Chicago and Washington DC.

I am interested to know if anyone has lived in either/both cities and could compare them if possible to Boston. My wife and I like the Boston area but we moved from London 15 years ago and still feel like we have a hard time fitting in (it's a bit clicky) and are ready for a change.

Which city would be a better fit in terms of social and family friendliness, housing, cost of living, weather, sports. My wife is a huge tennis player and I golf.

Thanks to anyone who can help.

[Reactionary]

I lived at Longfellow Place in Boston and have lived on Capitol Hill and Adams-Morgan in WDC.

Both places were good for me.

I found DC to be friendlier. Neither place seemed family-friendly unless you were in the suburbs. Housing was cheaper and bigger in DC. Cost of living was lower in DC (insurance, parking, entertainment). I enjoyed the Beacon Hill / Back Bay architecture of Boston and the townhouses of Capitol Hill / Georgetown / A-M. Subway is better in DC. Summer is sticky humid in DC, plus more storms, less snow. DC was better for playing sports (but I don't golf or tennis). DC was more convenient for going to Pro games.

[aragx6]

I think you might really like Chicago. The winter is the only reason not to move to Chicago imo, but we have the prettiest springs and falls and a lovely summer. The lake is freaking gorgeous, it's cheaper to live here than London, Boston or D.C., and while there are many young hip places in the city for partiers, there are also some absolutely wonderful family-friendly neighborhoods in the city, that are safe but still hip and walkable. Look into it, I bet you'd like it.