Place chicken wings and pickle juice in a large resealable plastic bag. Marinate in refrigerator for 4 hours or up to overnight.
Preheat oven to 400 degrees F. Line a baking sheet with foil. Place a greased, oven-safe baking rack over the prepared baking sheet. Set aside.
In a large bowl, combine ranch mix, dill, pepper and olive oil. Stir to make a paste. Set aside.
Remove wings from pickle juice and pat dry with paper towels. Add to bowl with ranch seasoning mixture and toss to coat wings evenly. Place wings on the prepared rack, making sure they aren't touching to ensure crispiness.
Bake for 40 to 45 minutes, flipping after 20 minutes.