Prior to Loyola University, Schilb was a postgraduate student at Brewster Academy in Wolfeboro, New Hampshire, during the 2002-2003 academic year.
A 6'7" (201 cm) guard (during his college days), Schilb played at Loyola University Chicago, with the Loyola Ramblers, from 2003 to 2007. In 2006, he became Loyola's first player since Alfredrick Hughes in 1985 to earn Associated Press All-American honors after averaging 19.1 points, 5.2 rebounds and 3.9 assists per game. He graduated from Loyola as the school's fourth all-time leading scorer (1,879 points) and all-time leader in three-point field goals (204).
After his junior season, Schilb became an early entry candidate for the 2006 NBA draft, but he withdrew his name before the deadline so he could return for his senior year. Schilb went undrafted by any NBA teams after his senior year.
Schilb signed with the French league team Élan Chalon in 2009. In his third season with the team, he was named LNB Pro A 2011–12 season French League Foreign Player MVP. In the final, he helped his team win the title with 20 points, 10 assists and 5 rebounds, earning the Final MVP award.
On August 2, 2012, Schlib extended his contract with Élan Chalon for one more season. In January 2013, Galatasaray offered 300,000 euros for a buyout of his contract and a salary that was three times larger than his current one, but Schlib turned down the offer. In his first EuroLeague season, he averaged 15.5 points, 4.6 rebounds and 4 assists over 10 games.
On June 23, 2013, he signed a three-year contract with the Serbian team Crvena zvezda Belgrade. On January 29, 2014, he officially parted ways with Crvena zvezda. The next day, he returned to France and signed with Paris-Levallois. On April 15, 2015, he parted ways with Paris.
On July 23, 2015, Schlib signed a one-year deal with the Turkish club Galatasaray. On July 28, 2016, he re-signed with Galatasaray for one more season.
Note: The EuroLeague is not the only competition in which the player participated for the team during the season. He also played in domestic competition, and regional competition if applicable.