diff --git a/pandas/core/algorithms.py b/pandas/core/algorithms.py
index 7494a8a54f9bb..1e112b61d0e62 100644
--- a/pandas/core/algorithms.py
+++ b/pandas/core/algorithms.py
@@ -1247,7 +1247,7 @@ def compute(self, method: str) -> Series:
             inds = inds[:n]
             findex = nbase
         else:
-            if len(inds) < nbase and len(nan_index) + len(inds) >= nbase:
+            if len(inds) < nbase <= len(nan_index) + len(inds):
                 findex = len(nan_index) + len(inds)
             else:
                 findex = len(inds)
diff --git a/pandas/core/arrays/_ranges.py b/pandas/core/arrays/_ranges.py
index 3bef3e59d5687..f50ce8a9ea895 100644
--- a/pandas/core/arrays/_ranges.py
+++ b/pandas/core/arrays/_ranges.py
@@ -121,12 +121,12 @@ def _generate_range_overflow_safe(
         return _generate_range_overflow_safe_signed(endpoint, periods, stride, side)
 
     elif (endpoint > 0 and side == "start" and stride > 0) or (
-        endpoint < 0 and side == "end" and stride > 0
+        endpoint < 0 < stride and side == "end"
     ):
         # no chance of not-overflowing
         raise OutOfBoundsDatetime(msg)
 
-    elif side == "end" and endpoint > i64max and endpoint - stride <= i64max:
+    elif side == "end" and endpoint - stride <= i64max < endpoint:
         # in _generate_regular_range we added `stride` thereby overflowing
         #  the bounds.  Adjust to fix this.
         return _generate_range_overflow_safe(
diff --git a/pandas/core/construction.py b/pandas/core/construction.py
index 997611d7860db..8fc77d47554dd 100644
--- a/pandas/core/construction.py
+++ b/pandas/core/construction.py
@@ -666,7 +666,7 @@ def range_to_ndarray(rng: range) -> np.ndarray:
         arr = np.arange(rng.start, rng.stop, rng.step, dtype="int64")
     except OverflowError:
         # GH#30173 handling for ranges that overflow int64
-        if (rng.start >= 0 and rng.step > 0) or (rng.stop >= 0 and rng.step < 0):
+        if (rng.start >= 0 and rng.step > 0) or (rng.step < 0 <= rng.stop):
             try:
                 arr = np.arange(rng.start, rng.stop, rng.step, dtype="uint64")
             except OverflowError:
diff --git a/pandas/plotting/_matplotlib/misc.py b/pandas/plotting/_matplotlib/misc.py
index 2f482c7d86571..9c054b5f03198 100644
--- a/pandas/plotting/_matplotlib/misc.py
+++ b/pandas/plotting/_matplotlib/misc.py
@@ -201,7 +201,7 @@ def normalize(series):
             ax.text(
                 xy[0] - 0.025, xy[1] - 0.025, name, ha="right", va="top", size="small"
             )
-        elif xy[0] < 0.0 and xy[1] >= 0.0:
+        elif xy[0] < 0.0 <= xy[1]:
             ax.text(
                 xy[0] - 0.025,
                 xy[1] + 0.025,
@@ -210,7 +210,7 @@ def normalize(series):
                 va="bottom",
                 size="small",
             )
-        elif xy[0] >= 0.0 and xy[1] < 0.0:
+        elif xy[1] < 0.0 <= xy[0]:
             ax.text(
                 xy[0] + 0.025, xy[1] - 0.025, name, ha="left", va="top", size="small"
             )
diff --git a/pandas/tests/io/formats/test_info.py b/pandas/tests/io/formats/test_info.py
index 54b5e699cd034..33c78baa1eedc 100644
--- a/pandas/tests/io/formats/test_info.py
+++ b/pandas/tests/io/formats/test_info.py
@@ -116,7 +116,7 @@ def test_info_verbose_check_header_separator_body():
     assert len(lines) > 0
 
     for i, line in enumerate(lines):
-        if i >= start and i < start + size:
+        if start <= i < start + size:
             line_nr = f" {i - start} "
             assert line.startswith(line_nr)
 
diff --git a/pyproject.toml b/pyproject.toml
index 55d20f4e1eaa0..de91edd62f457 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -100,7 +100,6 @@ disable = [
   "wrong-import-position",
 
   # pylint type "R": refactor, for bad code smell
-  "chained-comparison",
   "comparison-with-itself",
   "consider-merging-isinstance",
   "consider-using-ternary",
diff --git a/setup.py b/setup.py
index f0a81779a90b6..05d4407c7e959 100755
--- a/setup.py
+++ b/setup.py
@@ -355,8 +355,9 @@ def run(self):
         target_macos_version = "10.9"
         parsed_macos_version = parse_version(target_macos_version)
         if (
-            parse_version(str(python_target)) < parsed_macos_version
-            and parse_version(current_system) >= parsed_macos_version
+            parse_version(str(python_target))
+            < parsed_macos_version
+            <= parse_version(current_system)
         ):
             os.environ["MACOSX_DEPLOYMENT_TARGET"] = target_macos_version