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Preheat the oven to 400 degrees with a baking sheet on the bottom rack.
Toss the squash and carrots in a large bowl with the ground fennel and 2 tablespoons of the olive oil; season with salt and black pepper.
Spread the vegetables on the baking sheet and roast until almost tender.
Add the chickpeas to the baking sheet with the squash and carrots and drizzle with balsamic vinegar and olive oil.
Roast until the vegetables are browned and tender and the chickpeas have begun to crisp.
Combine all the roasted ingredients in a bowl, dress with vinegar and olive oil, add escarole, toss well.
Shred the ricotta salata over the top and sprinkle with toasted almonds.
Serve immediately.