diff --git a/python/pyspark/sql/column.py b/python/pyspark/sql/column.py
index 203e53474f74a..9357b4842bbdb 100644
--- a/python/pyspark/sql/column.py
+++ b/python/pyspark/sql/column.py
@@ -1388,10 +1388,12 @@ def when(self, condition: "Column", value: Any) -> "Column":
 
         Examples
         --------
+        Example 1: Using :func:`when` with conditions and values to create a new Column
+
         >>> from pyspark.sql import functions as sf
-        >>> df = spark.createDataFrame(
-        ...      [(2, "Alice"), (5, "Bob")], ["age", "name"])
-        >>> df.select(df.name, sf.when(df.age > 4, 1).when(df.age < 3, -1).otherwise(0)).show()
+        >>> df = spark.createDataFrame([(2, "Alice"), (5, "Bob")], ["age", "name"])
+        >>> result = df.select(df.name, sf.when(df.age > 4, 1).when(df.age < 3, -1).otherwise(0))
+        >>> result.show()
         +-----+------------------------------------------------------------+
         | name|CASE WHEN (age > 4) THEN 1 WHEN (age < 3) THEN -1 ELSE 0 END|
         +-----+------------------------------------------------------------+
@@ -1399,6 +1401,38 @@ def when(self, condition: "Column", value: Any) -> "Column":
         |  Bob|                                                           1|
         +-----+------------------------------------------------------------+
 
+        Example 2: Chaining multiple :func:`when` conditions
+
+        >>> from pyspark.sql import functions as sf
+        >>> df = spark.createDataFrame([(1, "Alice"), (4, "Bob"), (6, "Charlie")], ["age", "name"])
+        >>> result = df.select(
+        ...     df.name,
+        ...     sf.when(df.age < 3, "Young").when(df.age < 5, "Middle-aged").otherwise("Old")
+        ... )
+        >>> result.show()
+        +-------+---------------------------------------------------------------------------+
+        |   name|CASE WHEN (age < 3) THEN Young WHEN (age < 5) THEN Middle-aged ELSE Old END|
+        +-------+---------------------------------------------------------------------------+
+        |  Alice|                                                                      Young|
+        |    Bob|                                                                Middle-aged|
+        |Charlie|                                                                        Old|
+        +-------+---------------------------------------------------------------------------+
+
+        Example 3: Using literal values as conditions
+
+        >>> from pyspark.sql import functions as sf
+        >>> df = spark.createDataFrame([(2, "Alice"), (5, "Bob")], ["age", "name"])
+        >>> result = df.select(
+        ...     df.name, sf.when(sf.lit(True), 1).otherwise(
+        ...         sf.raise_error("unreachable")).alias("when"))
+        >>> result.show()
+        +-----+----+
+        | name|when|
+        +-----+----+
+        |Alice|   1|
+        |  Bob|   1|
+        +-----+----+
+
         See Also
         --------
         pyspark.sql.functions.when