Place all chowder ingredients except Milkadamia and vegetable stock in a large stockpot and sauté over medium heat, uncovered, stirring occasionally, until onion and fennel are translucent and tender to bite, 10-12 minutes.
Add Milkadamia and vegetable stock and turn heat to high, bringing to a simmer. Reduce heat to low, cover, and let simmer another 10-15 minutes. Transfer three quarters of the mixture to a blender and blend until completely creamy. Return to stockpot and stir to incorporate. Taste and adjust salt and pepper. Remove from heat and let sit, covered, while you make the chive fennel oil.
To make the chive fennel oil, combine all ingredients in a small food processor and pulse until mostly blended.
To serve, drizzle bowls of soup with chive fennel oil and top with fresh corn, minced fennel bulb, fennel fronds, flaky sea salt, and freshly cracked pepper.