The Colombian-American first got behind the wheel of a race car at the age of 13, winning a Skip Barber Racing Shoot-out scholarship. In his first full-season of competition, the former Easy Kart, Stars of Karting and Florida Winter Tour champion captured the Colombian Grand Prix Formula Renault 2000 title and finished as the series runner-up in the Skip Barber Eastern Regional Series. Building on this success, Chaves went undefeated in the 2006-07 Skip Barber Regional Southern Series, winning all 10 races. He continued his winning ways one year later, extending his Skip Barber Racing winning streak to 17 consecutive victories, leading the Skip Barber National Series before making the switch to Formula BMW Pacific competition where he finished in Fourth place. Chaves returned to the top of the championship charts in 2009, winning the final Formula BMW Americas title with five wins and podium finishes in every race.
In 2010, Chaves raced full-time in Europe, winning the Italian Formula 3 Championship Rookie of the Year award. He made his GP3 Series debut in 2011, earning five top-10 finishes in the highly competitive series. Chaves returned to North America in 2012, competing in the Mazda Road to Indy-backed Star Mazda Championship presented by Goodyear with JDC Motorsports, where he finished as the title runner-up with two wins. In 2013, Gabby competed in the Firestone Indy Lights championship with multiple-time champions Schmidt Peterson Motorsports, finishing as the title runner-up with ten podiums and one victory. In the Freedom 100, contested at the Indianapolis Motor Speedway just two days before the Indy 500, he finished second in a spectacular four-wide finish at the checkered flag, by a mere 0.0026 of a second – now the second-closest finish in Indianapolis Motor Speedway history.
Chaves returned to Indy Lights in 2014 and took the title on a tie-breaker of second place finishes. Earning eleven podium finishes and four victories, Chaves also won the Freedom 100 in decisive fashion, with a last-lap pass that earned him the victory he’d been denied in 2013. Aside from Indy Lights that season, he competed in the DeltaWing for legendary owner, Don Panoz, in the endurance races during the 2014 IMSA Tudor United Sportscar Championship. Chaves went on to win the Famous Six Hours of Bogota Endurance Race in Overall Class and Super GT Class. He was named Fan Favorite Colombian Driver of the Year and was awarded the FIA and FCAD best Colombian Driver of 2014.
Chaves graduated to the Verizon IndyCar Series with Bryan Herta Autosport, showing again that he is a fierce competitor with the raw talent and mindset, by winning the Indy 500 Sunoco Rookie of the Year award and Indycar Rookie of the Year Title. He also was invited by Honda Racing and Honda Performance Development to take part in the inaugural Tony Stewart Classic midget race