Hildebrand began karting at age fourteen in the Jim Russell Arrive and Drive Championship at Infineon Raceway in Northern California, winning his first race and the championship. He raced in Formula Russell in 2004, again taking the championship, and was chosen for the Team USA Scholarship, earning a ride in the Formula Palmer Audi Autumn Trophy. In 2006 he dominated the U.S. F2000 National Championship with Cape Motorsports, winning twelve of fourteen races and the title. He won the Gorsline Scholarship that year and was elected to the AARWBA All American Auto Racing First Team.
In 2007 he moved to the Champ Car Atlantic Series with Newman Wachs Racing, finishing seventh in points as the top American rookie. He spent 2008 in Indy Lights with RLR-Andersen Racing, recording his first series win at Kansas Speedway and finishing fifth in the championship. For 2009 he signed with AGR-AFS Racing, the defending championship team, and won four races while taking five pole positions to claim the Indy Lights title at the penultimate round at Chicagoland Speedway.
In December 2009 Hildebrand spent three days testing for the Force India Formula One team at the Jerez circuit, sharing the car with Paul di Resta.
Hildebrand made his IndyCar Series debut in 2010 for Dreyer and Reinbold Racing as a substitute for the injured Mike Conway. Later that year he signed a multi-year contract with Panther Racing to drive the No. 4 National Guard entry from 2011.
His 2011 Indianapolis 500 became one of the most replayed finishes in the race's history. Starting twelfth, he led at the halfway point and managed fuel strategy to run at the front in the closing laps. On the final lap, while passing the lapped Charlie Kimball through Turn 4, he slid into the outside wall, losing a wheel in the impact. Despite the damage, his car retained enough speed to cross the finish line in second place as Dan Wheldon swept past to take the victory. He was named Indianapolis 500 Rookie of the Year.
Later in the 2011 season, on October 16, Hildebrand was involved in the fifteen-car chain-reaction crash at Las Vegas Motor Speedway that claimed the life of Dan Wheldon. Hildebrand sustained an injured sternum and was transported to hospital for treatment.
He remained with Panther Racing through 2013, then drove for Ed Carpenter Racing in 2014, 2016 and 2017, and CFH Racing in 2015 for full-season campaigns. His best IndyCar championship season was 2012, when he finished eleventh overall. He recorded three career podiums, including a second place at Iowa and third at Phoenix in 2017 with Ed Carpenter Racing. From 2018 through 2020 he raced for Dreyer and Reinbold Racing in Indianapolis 500-only campaigns. In 2021 he drove for A.J. Foyt Enterprises in a car commemorating the sixtieth anniversary of Foyt's first Indianapolis 500 victory. He made two starts for the team in 2022, with the Indianapolis 500 that year being his final IndyCar start.
Hildebrand contested the Pikes Peak International Hill Climb in 2018 in a Porsche Cayman GT4 Clubsport, finishing second in the Porsche Trophy category behind Travis Pastrana. In 2022 he competed in the Open Wheel class at Pikes Peak driving a 2022 Dallara IR18 Evo IndyCar. In 2025 he ran the hill climb in a 1998 Kyle Petty Hot Wheels NASCAR Pontiac Grand Prix.
Hildebrand graduated from Redwood High School in Larkspur, California as a National Merit Scholar in 2006. He was accepted by UCLA, Berkeley and MIT; MIT granted him a three-year deferral which he eventually allowed to lapse as his racing career developed.
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