Chicago on “City crushes”, a list by Marcus Hsu on TheLysts.

Details

Photo
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Name
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Country
United States
Vibe in one line
Big-shouldered extrovert who actually remembers your name.
Rough population size
Roughly 2.7M in the city; ~9.5M in the metro.
Transit / getting around
L is solid in the core, buses fill in the grid, and the city actually understands what a bike lane is.
My take
Feels like the Midwest built a proper coastal city as a group project. If you fused Boston’s density with friendlier people and cheaper rents, you’d get something suspiciously Chicago-shaped.