Segares began his professional career with the Chicago Fire as a 2005 SuperDraft third round selection, and quickly proved himself during his rookie campaign. Segares was in the Fire's starting eleven for the first three games of the 2006 campaign until an ankle injury sidelined the young defender for a month of action. Upon his return, Segares came back with a vengeance, starting 19 of Chicago's last 24 games. Segares also helped the "Men in Red" earn an MLS club-record fourth Lamar Hunt U.S. Open Cup title in 2006, playing every minute in the tournament's Final. He held down the left side of defense in Chicago's starting XI in 2008 and 2009, while balancing his burgeoning duties for both club and country.
