Pour chili-lime seasoning onto a small plate. Rub the edge of a pint-sized jar with 1 lime wedge. Dip the edge of the jar into the seasoning. Fill jar with 1 cup ice and set aside.
Fill a cocktail shaker with remaining cup of ice, Bloody Mary mix, pickle juice, vodka, Worcestershire, and hot sauce. Squeeze in 1 lime wedge and 1 lemon wedge.
Roughly chop 1 fresh dill sprig and add to the shaker. Place lid on the shaker and shake for 10 seconds to combine. Strain into the prepared jar and garnish with pickle spear and remaining dill, lime, and lemon.
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