Chicago vs Philadelphia
Chicago comes out ahead overall, winning 2 of 7 criteria.
Summary
Chicago edges out Philadelphia overall (6.4 vs 6.4), but the margin is thin enough that a single strong priority — like climate — could reasonably flip your personal decision the other way.
Quick answers
Safety: Chicago (6/10 vs 5/10).
Climate: Philadelphia (5/10 vs 3/10).
Overall, Chicago scores higher (6.4/10 vs 6.4/10) across all seven criteria combined.
Cost of living: Chicago and Philadelphia tie on this (6/10 each).
Chicago — Chicago scores higher once we weight toward households with kids prioritizing safety, healthcare and clean air (6.4 vs 6.2 for Chicago vs Philadelphia), driven largely by safety.
Chicago and Philadelphia are a close call for remote work based on internet and cost of living.
Where each city wins
- +Safety: slightly better than Philadelphia (6.0 vs 5.0)
- +Healthcare: slightly better than Philadelphia (8.0 vs 7.0)
- +Climate: notably better than Chicago (5.0 vs 3.0)
Which city fits your profile?
Chicago and Philadelphia score within a rounding error of each other for remote workers who need fast internet and an affordable, pleasant base, so this comparison won't settle it either way.
Chicago and Philadelphia score within a rounding error of each other for independent workers balancing cost of living against healthcare access, so this comparison won't settle it either way.
Chicago scores higher once we weight toward households with kids prioritizing safety, healthcare and clean air (6.4 vs 6.2 for Chicago vs Philadelphia), driven largely by safety.
Chicago and Philadelphia score within a rounding error of each other for movers for whom affordability outweighs every other factor, so this comparison won't settle it either way.
Chicago scores higher once we weight toward people relocating somewhere unfamiliar who weigh personal safety above all (6.4 vs 6.1 for Chicago vs Philadelphia), driven largely by safety.
Chicago and Philadelphia score within a rounding error of each other for retirees prioritizing healthcare, climate and a calm environment over nightlife or internet speed, so this comparison won't settle it either way.
Chicago and Philadelphia score within a rounding error of each other for students who need affordability, transit and a lively social scene, so this comparison won't settle it either way.
Chicago scores higher once we weight toward expatriates relocating for work who lean on safety, healthcare and internet to stay settled and connected (6.8 vs 6.5 for Chicago vs Philadelphia), driven largely by safety.
Chicago and Philadelphia score within a rounding error of each other for founders and small business owners who need reliable connectivity and a livable base without big-city costs, so this comparison won't settle it either way.
Chicago and Philadelphia score within a rounding error of each other for early-career movers who want nightlife and transit within budget, without yet prioritizing healthcare or climate, so this comparison won't settle it either way.
Which city should you choose?
Pick Chicago if you're a young family, safety-first mover, or expat.