In 2007, Estrada received a commission to create a solo show about Russian playwright Anton Chekhov for the Twin Cities Chekhov Festival in Minneapolis, Minnesota. "Chek it, Baby: A Fabulous Explanation of Anton Chekhov's Fiercest Plays" earned favorable reviews when it premiered at Bryant-Lake Bowl the following year. In Lavender Magazine's "2008 Theatre Year in Review", John Townsend gave the show an Outstanding Touring Performance nod and wrote, "Jade Esteban Estrada actually put a queer spin on Anton Chekhov, the one playwright you may have thought was totally queer-resistant. If you ever had any doubt of Chekhov’s greatness, Estrada erases that." Tad Simons of Minneapolis-St. Paul Magazine called it "genuinely funny."