"The neighborhoods of Chicago" Now for me, Downtown Chicago is The Loop, part of the near north & south sides, and the Gold Coast. In other words, 990 N Michigan & Oak St to 2000 S Michigan to I55 (The Stevenson), West to I90 & I94. Both eastbound to LSD (Lake Shore Drive). When you leave this area, you're in the neighborhoods. If you're at Wrigley Field, you are in Wrigleyville (not downtown). If you're at Comiseky Park, you're in Bridgeport.