diff --git a/pandas/_typing.py b/pandas/_typing.py
index f3fc156cff556..d677564b5455e 100644
--- a/pandas/_typing.py
+++ b/pandas/_typing.py
@@ -21,6 +21,7 @@
     Dict,
     Hashable,
     List,
+    Literal,
     Mapping,
     Optional,
     Sequence,
@@ -37,7 +38,6 @@
 # https://mypy.readthedocs.io/en/latest/common_issues.html#import-cycles
 if TYPE_CHECKING:
     from typing import (
-        Literal,
         TypedDict,
         final,
     )
@@ -200,10 +200,7 @@
 ]
 
 # Arguments for fillna()
-if TYPE_CHECKING:
-    FillnaOptions = Literal["backfill", "bfill", "ffill", "pad"]
-else:
-    FillnaOptions = str
+FillnaOptions = Literal["backfill", "bfill", "ffill", "pad"]
 
 # internals
 Manager = Union[
diff --git a/pandas/core/algorithms.py b/pandas/core/algorithms.py
index 06ad571fb0c00..a467798adf2e4 100644
--- a/pandas/core/algorithms.py
+++ b/pandas/core/algorithms.py
@@ -8,6 +8,7 @@
 from textwrap import dedent
 from typing import (
     TYPE_CHECKING,
+    Literal,
     Union,
     cast,
 )
@@ -79,7 +80,6 @@
 from pandas.core.indexers import validate_indices
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas import (
         Categorical,
diff --git a/pandas/core/arrays/base.py b/pandas/core/arrays/base.py
index 96bd4280f4da4..86a9eb9c4c32a 100644
--- a/pandas/core/arrays/base.py
+++ b/pandas/core/arrays/base.py
@@ -14,6 +14,7 @@
     Any,
     Callable,
     Iterator,
+    Literal,
     Sequence,
     TypeVar,
     cast,
@@ -72,7 +73,6 @@
 )
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     class ExtensionArraySupportsAnyAll("ExtensionArray"):
         def any(self, *, skipna: bool = True) -> bool:
diff --git a/pandas/core/arrays/datetimelike.py b/pandas/core/arrays/datetimelike.py
index 08cb12a1373bb..8b5bda4629506 100644
--- a/pandas/core/arrays/datetimelike.py
+++ b/pandas/core/arrays/datetimelike.py
@@ -9,6 +9,7 @@
     TYPE_CHECKING,
     Any,
     Callable,
+    Literal,
     Sequence,
     TypeVar,
     Union,
@@ -121,7 +122,6 @@
 from pandas.tseries import frequencies
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas.core.arrays import (
         DatetimeArray,
diff --git a/pandas/core/arrays/datetimes.py b/pandas/core/arrays/datetimes.py
index 92a906e9fd8b0..0a517b22d1bb3 100644
--- a/pandas/core/arrays/datetimes.py
+++ b/pandas/core/arrays/datetimes.py
@@ -8,6 +8,7 @@
 )
 from typing import (
     TYPE_CHECKING,
+    Literal,
     cast,
     overload,
 )
@@ -81,7 +82,6 @@
 )
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas import DataFrame
     from pandas.core.arrays import (
diff --git a/pandas/core/base.py b/pandas/core/base.py
index a7a67a1f77ea3..430f1b57f0b87 100644
--- a/pandas/core/base.py
+++ b/pandas/core/base.py
@@ -10,6 +10,7 @@
     Any,
     Generic,
     Hashable,
+    Literal,
     TypeVar,
     cast,
 )
@@ -64,7 +65,6 @@
 import pandas.core.nanops as nanops
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas import Categorical
 
diff --git a/pandas/core/dtypes/cast.py b/pandas/core/dtypes/cast.py
index 52254ff4cdb9b..9f0fefc9a10d0 100644
--- a/pandas/core/dtypes/cast.py
+++ b/pandas/core/dtypes/cast.py
@@ -14,6 +14,7 @@
 from typing import (
     TYPE_CHECKING,
     Any,
+    Literal,
     Sized,
     TypeVar,
     cast,
@@ -93,7 +94,6 @@
 )
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas.core.arrays import (
         DatetimeArray,
diff --git a/pandas/core/frame.py b/pandas/core/frame.py
index f63ebd2156fc2..2466154f78294 100644
--- a/pandas/core/frame.py
+++ b/pandas/core/frame.py
@@ -27,6 +27,7 @@
     Hashable,
     Iterable,
     Iterator,
+    Literal,
     Sequence,
     cast,
     overload,
@@ -207,7 +208,6 @@
 import pandas.plotting
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas._typing import (
         TimedeltaConvertibleTypes,
diff --git a/pandas/core/generic.py b/pandas/core/generic.py
index 4019ef8537294..f1a5a565fc861 100644
--- a/pandas/core/generic.py
+++ b/pandas/core/generic.py
@@ -14,6 +14,7 @@
     AnyStr,
     Callable,
     Hashable,
+    Literal,
     Mapping,
     Sequence,
     cast,
@@ -154,7 +155,6 @@
 from pandas.io.formats.printing import pprint_thing
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas._libs.tslibs import BaseOffset
     from pandas._typing import RandomState
diff --git a/pandas/core/groupby/groupby.py b/pandas/core/groupby/groupby.py
index a3a894560edfd..ba80f7329202d 100644
--- a/pandas/core/groupby/groupby.py
+++ b/pandas/core/groupby/groupby.py
@@ -24,6 +24,7 @@ class providing the base-class of operations.
     Iterable,
     Iterator,
     List,
+    Literal,
     Mapping,
     Sequence,
     TypeVar,
@@ -109,7 +110,6 @@ class providing the base-class of operations.
 )
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas._typing import RandomState
 
diff --git a/pandas/core/indexes/base.py b/pandas/core/indexes/base.py
index 86df4854db01d..2f1d85f1340a4 100644
--- a/pandas/core/indexes/base.py
+++ b/pandas/core/indexes/base.py
@@ -9,6 +9,7 @@
     Any,
     Callable,
     Hashable,
+    Literal,
     Sequence,
     TypeVar,
     cast,
@@ -159,7 +160,6 @@
 )
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas import (
         CategoricalIndex,
diff --git a/pandas/core/resample.py b/pandas/core/resample.py
index 76e23f1bf77e0..40a208a24699a 100644
--- a/pandas/core/resample.py
+++ b/pandas/core/resample.py
@@ -4,9 +4,9 @@
 from datetime import timedelta
 from textwrap import dedent
 from typing import (
-    TYPE_CHECKING,
     Callable,
     Hashable,
+    Literal,
     no_type_check,
 )
 
@@ -88,9 +88,6 @@
     Tick,
 )
 
-if TYPE_CHECKING:
-    from typing import Literal
-
 _shared_docs_kwargs: dict[str, str] = {}
 
 
diff --git a/pandas/core/series.py b/pandas/core/series.py
index a0c974428d875..6e6e8b6d8b178 100644
--- a/pandas/core/series.py
+++ b/pandas/core/series.py
@@ -13,6 +13,7 @@
     Callable,
     Hashable,
     Iterable,
+    Literal,
     Sequence,
     Union,
     cast,
@@ -140,7 +141,6 @@
 import pandas.plotting
 
 if TYPE_CHECKING:
-    from typing import Literal
 
     from pandas._typing import (
         TimedeltaConvertibleTypes,