December offers distinct seasonal experiences at both ends of the GPT–MDW route. Near Gulfport-Biloxi International Airport (GPT), enjoy holiday light shows, casino holiday events, and coastal winter dining; popular nearby destinations include Biloxi, Pascagoula, and New Orleans for extended holiday weekends. At Chicago Midway International Airport (MDW), December highlights include Christkindlmarket (a traditional German-style holiday market), ZooLights at Lincoln Park Zoo, ice skating at Millennium Park, and festive Magnificent Mile window displays. Use event dates to plan travel—arriving earlier in December usually yields better airfare and hotel availability.