Cook bacon as indicated on package, allowing to crisp. Pour excess fat into a large stock pot or Dutch oven. Crumble bacon and place aside.
Heat stock pot with fat drippings over medium-high. Slice green onions, celery, and squash; toss into pot. Stir to coat and cook for 8 minutes, continuing to stir occasionally. (Reduce heat if veggies start to burn.)
Mince garlic and add to pot; stir for 1 minute. Reduce heat to medium and add 1 1/2 cups milk, 1 1/2 cups corn, thyme, salt, and pepper. Continue to cook, stirring occasionally.
Meanwhile, add remaining corn and milk, and the cream to a blender; mix well. Add purée to stock pot. Stir and allow to heat through.
Top soup with crumbled bacon. Serve with a slice of Italian bread and pineapple chunks on the side.