Fans of the Oscar-winning actor are being asked to donate £5 to buy a homeless person a meal and a hot drink to have a chance of dining with the star.
All donations will go towards feeding the homeless at Edinburgh’s Home, a new restaurant from the teams behind social enterprise Social Bite and restaurant Maison Bleue.
His visit comes following a similar trip by George Clooney last year - who drew crowds of hundreds when he visited the Social Bite cafe, which donates all its profits to homeless people, leaving $1000 (about £650) at the cafe for the cause.
Whilst he’s in town, DiCaprio will also deliver a keynote speech alongside Sir Tom Hunter at the Scottish Business Awards.
As well as Clooney, the actor follows in the footsteps of former US president Bill Clinton, who delivered the same address in 2013, and renowned entrepreneur Sir Richard Branson in 2014.
As well as lunch with 41-year-old DiCaprio, the competition winner will receive an overnight stay with dinner at The George Hotel, 1st class travel within Scotland with ScotRail and a £1,000 Champagne and shopping experience at ROX, George Street.
Scottish Business Awards chairman Sir Tom Hunter said: “Leonardo is not only a famous actor, he is a pioneering environmentalist and committed philanthropist whose charitable work is making a global impact.
“To have him address our nation’s premier businesses and entrepreneurs is incredibly exciting.
“That the Scottish Business Awards is the largest awards dinner of its kind in the whole of the UK says a lot about the strength and ambition of Scotland’s entrepreneurial community.
“November 17 is set to be another very special night.”
Last year more than £400,000 was donated to homeless enterprise Social Bite.
The winner will be selected and informed on Friday 11 November and participants must be available in Edinburgh on November 17.
You can enter here: https://www.itison.com/Edinburgh/deals/donate-5-and-enter-the-prize-draw