diff --git a/.changelog/_unreleased.toml b/.changelog/_unreleased.toml
new file mode 100644
index 0000000..d5f3ad4
--- /dev/null
+++ b/.changelog/_unreleased.toml
@@ -0,0 +1,5 @@
+[[entries]]
+id = "6d0f41f2-f7f9-4808-af65-196a7a909b4f"
+type = "fix"
+description = "Fix #47: Union with Literal in them can now de/serialize"
+author = "@rhaps0dy"
diff --git a/databind/src/databind/json/converters.py b/databind/src/databind/json/converters.py
index e04df80..fbb1322 100644
--- a/databind/src/databind/json/converters.py
+++ b/databind/src/databind/json/converters.py
@@ -763,13 +763,19 @@ def _check_style_compatibility(self, ctx: Context, style: str, value: t.Any) ->
     def convert(self, ctx: Context) -> t.Any:
         datatype = ctx.datatype
         union: t.Optional[Union]
+        literal_types: t.List[TypeHint] = []
+
         if isinstance(datatype, UnionTypeHint):
             if datatype.has_none_type():
                 raise NotImplementedError("unable to handle Union type with None in it")
-            if not all(isinstance(a, ClassTypeHint) for a in datatype):
-                raise NotImplementedError(f"members of plain Union must be concrete types: {datatype}")
-            members = {t.cast(ClassTypeHint, a).type.__name__: a for a in datatype}
-            if len(members) != len(datatype):
+
+            literal_types = [a for a in datatype if isinstance(a, LiteralTypeHint)]
+            non_literal_types = [a for a in datatype if not isinstance(a, LiteralTypeHint)]
+            if not all(isinstance(a, ClassTypeHint) for a in non_literal_types):
+                raise NotImplementedError(f"members of plain Union must be concrete or Literal types: {datatype}")
+
+            members = {t.cast(ClassTypeHint, a).type.__name__: a for a in non_literal_types}
+            if len(members) != len(non_literal_types):
                 raise NotImplementedError(f"members of plain Union cannot have overlapping type names: {datatype}")
             union = Union(members, Union.BEST_MATCH)
         elif isinstance(datatype, (AnnotatedTypeHint, ClassTypeHint)):
@@ -788,6 +794,11 @@ def convert(self, ctx: Context) -> t.Any:
                     return ctx.spawn(ctx.value, member_type, None).convert()
                 except ConversionError as exc:
                     errors.append((exc.origin, exc))
+            for literal_type in literal_types:
+                try:
+                    return ctx.spawn(ctx.value, literal_type, None).convert()
+                except ConversionError as exc:
+                    errors.append((exc.origin, exc))
             raise ConversionError(
                 self,
                 ctx,
diff --git a/databind/src/databind/json/tests/converters_test.py b/databind/src/databind/json/tests/converters_test.py
index 0de421c..2b6cadf 100644
--- a/databind/src/databind/json/tests/converters_test.py
+++ b/databind/src/databind/json/tests/converters_test.py
@@ -30,6 +30,7 @@
     DatetimeConverter,
     DecimalConverter,
     EnumConverter,
+    LiteralConverter,
     MappingConverter,
     OptionalConverter,
     PlainDatatypeConverter,
@@ -328,6 +329,22 @@ def test_union_converter_best_match(direction: Direction) -> None:
         assert mapper.convert(direction, 42, t.Union[int, str]) == 42
 
 
+@pytest.mark.parametrize("direction", (Direction.SERIALIZE, Direction.DESERIALIZE))
+def test_union_converter_best_match_literal(direction: Direction) -> None:
+    mapper = make_mapper([UnionConverter(), PlainDatatypeConverter(), LiteralConverter()])
+
+    LiteralUnionType = t.Union[int, t.Literal["hi"], t.Literal["bye"]]
+
+    if direction == Direction.DESERIALIZE:
+        assert mapper.convert(direction, 42, LiteralUnionType) == 42
+        assert mapper.convert(direction, "hi", LiteralUnionType) == "hi"
+        assert mapper.convert(direction, "bye", LiteralUnionType) == "bye"
+    else:
+        assert mapper.convert(direction, 42, LiteralUnionType) == 42
+        assert mapper.convert(direction, "hi", LiteralUnionType) == "hi"
+        assert mapper.convert(direction, "bye", LiteralUnionType) == "bye"
+
+
 @pytest.mark.parametrize("direction", (Direction.SERIALIZE, Direction.DESERIALIZE))
 def test_union_converter_keyed(direction: Direction) -> None:
     mapper = make_mapper([UnionConverter(), PlainDatatypeConverter()])
@@ -339,6 +356,31 @@ def test_union_converter_keyed(direction: Direction) -> None:
         assert mapper.convert(direction, 42, th) == {"int": 42}
 
 
+@pytest.mark.xfail
+@pytest.mark.parametrize("direction", (Direction.SERIALIZE, Direction.DESERIALIZE))
+def test_union_converter_keyed_literal(direction: Direction) -> None:
+    mapper = make_mapper([UnionConverter(), PlainDatatypeConverter(), LiteralConverter()])
+
+    th = te.Annotated[
+        t.Union[int, t.Literal["hi"], t.Literal["bye"]],
+        Union({"int": int, "HiType": t.Literal["hi"], "ByeType": t.Literal["bye"]}, style=Union.KEYED),
+    ]
+    if direction == Direction.DESERIALIZE:
+        assert mapper.convert(direction, {"int": 42}, th) == 42
+        assert mapper.convert(direction, {"HiType": "hi"}, th) == "hi"
+        assert mapper.convert(direction, {"ByeType": "bye"}, th) == "bye"
+
+        with pytest.raises(ConversionError):
+            mapper.convert(direction, {"ByeType": "hi"}, th)
+    else:
+        assert mapper.convert(direction, 42, th) == {"int": 42}
+        assert mapper.convert(direction, "hi", th) == {"HiType": "hi"}
+        assert mapper.convert(direction, "bye", th) == {"ByeType": "bye"}
+
+        with pytest.raises(ConversionError):
+            mapper.convert(direction, {"ByeType": "hi"}, th)
+
+
 @pytest.mark.parametrize("direction", (Direction.SERIALIZE, Direction.DESERIALIZE))
 def test_union_converter_flat_plain_types_not_supported(direction: Direction) -> None:
     mapper = make_mapper([UnionConverter(), PlainDatatypeConverter()])