Southwest® flights from Colorado Springs to Chicago (Midway) from $91

When you touch down at Chicago Midway International Airport, you’ll find yourself on the southwest edge of the city and just a short Orange Line ‘L’ ride away from the center of the hustle and bustle—the Loop. What Chicago calls its downtown area, the Loop and its surrounding neighborhoods are home to colleges, theatres, museums, world-class shopping, and Michelin-starred restaurants. Where to begin? Whether you choose to ride the “L” or rent a car, there’s plenty for everyone to explore in the Loop and among the city’s 77 distinct neighborhoods.

If you choose to explore the Loop and the lakefront, consider seeing everything the Museum Campus has to offer. Inside sprawling lakefront Grant Park, the campus is home to five of Chicago’s most beloved attractions, including the Adler Planetarium, the Shedd Aquarium, and the Field Museum of Natural History. Originally called the Columbian Museum of Chicago and established for the 1983 World’s Columbian Exposition, the Field Museum is home to Sue, the largest and most complete Tyrannosaurus rex skeleton so far discovered. If you prefer the stars to terra firma, the Adler Planetarium offers visitors the chance to explore several space science exhibitions year-round.