diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index 88de9341..93b706d7 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -31,6 +31,7 @@ unreleased
 * introduce Y027 (Python 2-incompatible extension of Y022)
 * all errors are now enabled by default
 * introduce Y029 (never define ``__repr__`` or ``__str__``)
+* introduce Y030 (use ``Literal['foo', 'bar']`` instead of ``Literal['foo'] | Literal['bar']``)
 
 20.10.0
 ~~~~~~~
diff --git a/README.rst b/README.rst
index d1fdbcdd..0bfb6865 100644
--- a/README.rst
+++ b/README.rst
@@ -100,6 +100,9 @@ currently emitted:
 * Y029: It is almost always redundant to define ``__str__`` or ``__repr__`` in
   a stub file, as the signatures are almost always identical to
   ``object.__str__``and ``object.__repr__``.
+* Y030: Union expressions should never have more than one ``Literal`` member,
+  as ``Literal[1] | Literal[2]`` is semantically identical to
+  ``Literal[1, 2]``.
 
 Many error codes enforce modern conventions, and some cannot yet be used in
 all cases:
diff --git a/pyi.py b/pyi.py
index d7800ad0..78fb7801 100644
--- a/pyi.py
+++ b/pyi.py
@@ -421,9 +421,52 @@ def _check_union_members(self, members: Sequence[ast.expr]) -> None:
         for member in members:
             members_by_dump.setdefault(ast.dump(member), []).append(member)
 
-        for members in members_by_dump.values():
-            if len(members) >= 2:
-                self.error(members[1], Y016.format(unparse(members[1])))
+        dupes_in_union = False
+        for member_list in members_by_dump.values():
+            if len(member_list) >= 2:
+                self.error(member_list[1], Y016.format(unparse(member_list[1])))
+                dupes_in_union = True
+
+        if not dupes_in_union:
+            self._check_for_multiple_literals(members)
+
+    def _check_for_multiple_literals(self, members: Sequence[ast.expr]) -> None:
+        literals_in_union, non_literals_in_union = [], []
+
+        for member in members:
+            if (
+                isinstance(member, ast.Subscript)
+                and isinstance(member.value, ast.Name)
+                and member.value.id == "Literal"
+            ):
+                literals_in_union.append(member.slice)
+            else:
+                non_literals_in_union.append(member)
+
+        if len(literals_in_union) < 2:
+            return
+
+        new_literal_members: list[ast.expr] = []
+
+        for literal in literals_in_union:
+            if sys.version_info >= (3, 9):
+                contents = literal
+            else:
+                contents = literal.value
+
+            if isinstance(contents, ast.Tuple):
+                new_literal_members.extend(contents.elts)
+            else:
+                new_literal_members.append(contents)
+
+        new_literal_slice = unparse(ast.Tuple(new_literal_members)).strip("()")
+
+        if non_literals_in_union:
+            suggestion = f'Combine them into one, e.g. "Literal[{new_literal_slice}]".'
+        else:
+            suggestion = f'Use a single Literal, e.g. "Literal[{new_literal_slice}]".'
+
+        self.error(members[0], Y030.format(suggestion=suggestion))
 
     def visit_BinOp(self, node: ast.BinOp) -> None:
         if not isinstance(node.op, ast.BitOr):
@@ -905,3 +948,4 @@ def parse_options(cls, optmanager, options, extra_args):
 Y027 = 'Y027 Use {good_cls_name} instead of "{bad_cls_alias}"'
 Y028 = "Y028 Use class-based syntax for NamedTuples"
 Y029 = "Y029 Defining __repr__ or __str__ in a stub is almost always redundant"
+Y030 = "Y030 Multiple Literal members in a union. {suggestion}"
diff --git a/tests/union_duplicates.pyi b/tests/union_duplicates.pyi
index 564baba4..3c658fc0 100644
--- a/tests/union_duplicates.pyi
+++ b/tests/union_duplicates.pyi
@@ -1,4 +1,5 @@
 from typing import Union
+from typing_extensions import Literal, TypeAlias
 
 def f1_pipe(x: int | str) -> None:
     ...
@@ -21,3 +22,10 @@ def f4_union(x: Union[int, None, int]) -> None:  # Y016 Duplicate union member "
     ...
 def f5_union(x: Union[int, int, None]) -> None:  # Y016 Duplicate union member "int"
     ...
+
+
+just_literals_subscript_union: Union[Literal[1], Literal[2]]  # Y030 Multiple Literal members in a union. Use a single Literal, e.g. "Literal[1, 2]".
+mixed_subscript_union: Union[str, Literal['foo'], Literal['bar']]  # Y030 Multiple Literal members in a union. Combine them into one, e.g. "Literal['foo', 'bar']".
+just_literals_pipe_union: TypeAlias = Literal[True] | Literal['idk']  # Y030 Multiple Literal members in a union. Use a single Literal, e.g. "Literal[True, 'idk']".
+mixed_pipe_union: TypeAlias = Union[Literal[966], int, Literal['baz']]  # Y030 Multiple Literal members in a union. Combine them into one, e.g. "Literal[966, 'baz']".
+many_literal_members_but_needs_combining: TypeAlias = int | Literal['a', 'b'] | Literal['baz']  # Y030 Multiple Literal members in a union. Combine them into one, e.g. "Literal['a', 'b', 'baz']".