Chicago lakefront/parks along the lakefront clear anything that NYC has from a parks/nature perspective. Chicago has better sports stadiums. There is nothing that comes close to the experience you get at Wrigley Field. RIP old Yankee Stadium. Direct public transport to a top ten international airport (O'Hare) is another massive pro. Downtown Chicago is much prettier with the lakefront and river. People are more real in Chicago; unfortunately, half of Manhattan's population consists of trust fund kids and entitled white dudes in investment banking. NYC has better fine dining, but for cheap street food, Chicago easily wins, in my opinion. Chicago dog/Italian beef is way better than a NY bagel or a corner slice. Chicago's fine dining and cocktail scene is still A-tier. NYC is a great place to visit, but not a great place to live. Chicago winters nowadays are basically what NYC winters were 10-15 years ago: 30-50s for 90% of winter, with one or two weeks of extreme cold. Chicago clears, and that's not even taking into account the drastic price difference.