Orton attended Southeast Polk High School in Pleasant Hill, Iowa, where he was a four-sport star in football, basketball, tennis, and track & field.

He earned honorable mention all-state and first-team all-conference his senior year, after completing 95 of 192 attempts (49.5%), 1,366 yards with 12 touchdowns, and 5 interceptions.

In 2004, Orton was the preseason third-team All-American quarterback, behind USC's Matt Leinart and Oklahoma's Jason White as well as a Heisman Trophy hopeful early in the season.

Orton was able to return to the field in the 4th quarter against Ohio State to help the Boilermakers get the go ahead TD to overcome the Buckeyes and snap their losing streak.

[8] In the 2005 NFL season, he was rushed into the Bears starting lineup as a rookie after a preseason injury to starter Rex Grossman, and the poor play of back-up Chad Hutchinson.

Orton started 15 games of the season, but was replaced by Grossman after halftime during the Bears' Week 15 victory against the Atlanta Falcons.

The Bears had already clinched the NFC North championship and a first-round bye in the 2005–06 playoffs with their Week 16 victory over the Green Bay Packers.

He completed sixteen of twenty-five passes for 151 yards and one touchdown en route to leading the Bears to a comeback victory over the Houston Texans.

[14] After the Bears lost their chances of making a postseason berth, Lovie Smith chose to start Orton over Griese.

[16] He improved in the final two games of the season, leading the Bears to two consecutive victories, passing for 294 yards, 3 touchdowns and an interception.

On August 18, after deadlock against Grossman in games with the Kansas City Chiefs and Seattle Seahawks, Bears head coach Lovie Smith named Orton the team's starting QB for the 2008 season in Week 3 of the preseason, despite not throwing a pass over 17 yards or for a touchdown in the first two preseason games.

From the start of November 2008, Kyle Orton passed for ten touchdowns, and four interceptions, leading the Bears to a 4–3 record.

[21] Coach Lovie Smith was pleased with Orton's performance and believed he would be the team's starting quarterback for the following season.

[22] However, Jerry Angelo, the team's general manager, stated he wished to further solidify the quarterback position in the long run.

His most impressive effort in that streak came against the New England Patriots, when he completed 35–48 passes for 330 yards and orchestrated a 98-yard drive to tie the game and send it into overtime.

He threw his first interception of the season to Randy Moss, who came in to help on the attempted Hail Mary pass, at the end of the first half.

For the 2009 season (playing in 16 games with 15 starts), Orton threw 21 touchdown passes and 12 interceptions with an 86.8 QB rating.

Tim Tebow was named the starter the following week by interim coach Eric Studesville and played the last three games of the season.

The team had a 1–4 start with Orton throwing 8 touchdowns and 7 interceptions as the starter, accumulating 979 yards and completing 58.7% of his passes.

[29] He was replaced as the starter by Tim Tebow during the week 5 contest against the San Diego Chargers, and Orton never took another snap for the Broncos.

He was claimed off waivers by the Kansas City Chiefs on November 23, 2011, after a season-ending injury to starting quarterback Matt Cassel.

Chicago (looking to replace injured Jay Cutler) and the Dallas Cowboys (because of concerns of injuries to backup quarterback Jon Kitna) also made claims on him.

[31] On December 4, 2011, in a game against his former team, the Chicago Bears, Orton came into the second quarter to relieve Tyler Palko, but was injured on his first pass attempt.

On December 27, 2013, head coach Jason Garrett announced that Orton would be the starting quarterback for the week 17 game against the Philadelphia Eagles after Tony Romo underwent back surgery.

Besides accumulating $70,000 in fines, quarterback coach Wade Wilson reported that Orton did not maintain any communications with the Cowboys during this period.

[37] Orton, who risked losing part of his signing bonus by holding out, eventually showed up to training camp.

On August 29, 2014, Orton agreed on a two-year deal with the Buffalo Bills, with the team paying him $5 million in the first year alone, making him the highest paid backup quarterback in the league.