For Swift 4.2 (Xcode 10) and later

There's a CaseIterable protocol:

enum EstimateItemStatus: String, CaseIterable {
    case pending = "Pending"
    case onHold = "OnHold"
    case done = "Done"

    init?(id : Int) {
        switch id {
        case 1: self = .pending
        case 2: self = .onHold
        case 3: self = .done
        default: return nil
        }
    }
}

for value in EstimateItemStatus.allCases {
    print(value)
}

For Swift < 4.2

No, you can't query an enum for what values it contains. See this article. You have to define an array that list all the values you have. Also check out Frank Valbuena's solution in "How to get all enum values as an array".

enum EstimateItemStatus: String {
    case Pending = "Pending"
    case OnHold = "OnHold"
    case Done = "Done"

    static let allValues = [Pending, OnHold, Done]

    init?(id : Int) {
        switch id {
        case 1:
            self = .Pending
        case 2:
            self = .OnHold
        case 3:
            self = .Done
        default:
            return nil
        }
    }
}

for value in EstimateItemStatus.allValues {
    print(value)
}