I hate to compare cities. But... Austin may be one sunbelt city that urbanizes just because of its demographics (young tech workforce). Right now though, its still a baby.
Austin 305 sq mi, population ~1,000,000. Metro ~2,200,000. Skyline, modest
Chicago 234 sq mi, population ~2,800,000. Metro ~9,830,000. Skyline, spectacular
Austin also has bizarre zoning to protect capitol views from around the city, so who really knows how its downtown will evolve as the city grows. My guess is probably more like Houston then Chicago.
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Chicago Blackhawks, Stanley Cup Champs 2010, 2013, 2015.
Chicago White Sox, World Series Champs 2005.
Chicago Bulls, World Champs 1991, 1992, 1993, 1996, 1997, 1998.
Chicago Bears, Super Bowl Champs 1985.
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