Southwest® flights from Atlanta to Chicago-Midway from $99

Atlantans will agree that there's no singular, homogeneous Atlanta. The same can be said of Chicago. Known as a city of neighborhoods—the untracked, unofficial count ranges somewhere around 200—Chicago boasts 77 distinct community areas. Chances are that when you think of Chicago, you think of the Loop—the city's downtown. But the north, west, and south sides of the city, and everything in between, are each unique and full of potential adventure.

When you deplane at Midway, downtown Chicago is a quick half-hour ride on the Orange Line train away. Cabs, rideshares, and rental cars are options too, of course, but the CTA system is an affordable option for navigating the city on a budget—and a great way to get a glimpse of the skyline and some neighborhood color. Visitors coming for business or with busy schedules can get a taste of the city without disrupting their agenda.