Southwest® flights from Boston to Chicago-Midway from $101

Trade in the T for the ‘L’—when you deplane at Midway, you’ll find yourself on the Southwest side of Chicago and a 30-minute ‘L’ train ride away from downtown (what Chicago calls “the Loop”). From there, you can reach the whole city by public transit—the ‘L’ or buses—and begin your adventure, heading in whatever direction you choose. Shopping and theatre fans will want to stick around the Loop and adjacent areas for the Magnificent Mile shopping options and the Downtown Theatre District attractions. Fine dining fans should hop on the Pink or Green Line and head to Restaurant Row in the West Loop, home to what is widely believed to be the best cheeseburger around, Michelin-starred plates, and street food favorites—something to please every palate in the party.

Chicago is a city of neighborhoods. The city is composed of 77 community areas, each with their own storied history and hidden gems. A great way to take it all in—or narrow down where to start—is to visit the Chicago History Museum (in the Old Town Triangle neighborhood on the Northside). Fans of walking tours can traverse Chi-Town by tracing the footsteps of notorious Mafioso Al Capone, or exploring the examples of Prairie School housing stock and the surviving examples of Frank Lloyd Wright’s work. Whether you find affinity with Cubs fans or Sox fans, there’s something for everyone in each side of the City of the Big Shoulders.