From Roosevelt subway to Chicago Midway airport, fly to Ft. Myers airport, then taxi to Fort Myers. 5hrs 37min $217. From Monroe-Blue subway to Chicago O'Hare airport, fly to Ft. Myers airport, then taxi to Fort Myers. 5hrs 47min $217. From Chicago, IL bus to Civic Center Station, train to Atlanta, GA, bus to Fort Myers, FL, then taxi to Fort Myers. 24hrs 54min $304. From Chicago, IL train to Alexandria, VA, train to Nebraska Av @ Twiggs St, line 46 bus to Tampa, FL, then bus to Ft. Myers, FL. 2days 02hrs $362. From Chicago drive to Fort Myers. 21hrs 14min $163.