diff --git a/.github/workflows/linux.yml b/.github/workflows/linux.yml
index 0f91d5528625..22df4061c113 100644
--- a/.github/workflows/linux.yml
+++ b/.github/workflows/linux.yml
@@ -64,6 +64,9 @@ jobs:
         - llvm_version: 13.0.0
           llvm_url: https://github.com/llvm/llvm-project/releases/download/llvmorg-13.0.0/clang+llvm-13.0.0-x86_64-linux-gnu-ubuntu-20.04.tar.xz
           base_image: ubuntu-20.04
+        - llvm_version: 14.0.0
+          llvm_url: https://github.com/llvm/llvm-project/releases/download/llvmorg-14.0.0/clang+llvm-14.0.0-x86_64-linux-gnu-ubuntu-18.04.tar.xz
+          base_image: ubuntu-18.04
     runs-on: ${{ matrix.base_image }}
     name: "Test LLVM ${{ matrix.llvm_version }} (${{ matrix.base_image }})"
     steps:
diff --git a/src/llvm/ext/llvm-versions.txt b/src/llvm/ext/llvm-versions.txt
index 06ce7214188b..405fc1147bde 100644
--- a/src/llvm/ext/llvm-versions.txt
+++ b/src/llvm/ext/llvm-versions.txt
@@ -1 +1 @@
-13.0 12.0 11.1 11.0 10.0 9.0 8.0 7.1 6.0 5.0 4.0 3.9 3.8
+14.0 13.0 12.0 11.1 11.0 10.0 9.0 8.0 7.1 6.0 5.0 4.0 3.9 3.8
diff --git a/src/llvm/ext/llvm_ext.cc b/src/llvm/ext/llvm_ext.cc
index c6f5dd86bb10..18102ceb23b4 100644
--- a/src/llvm/ext/llvm_ext.cc
+++ b/src/llvm/ext/llvm_ext.cc
@@ -209,8 +209,8 @@ LLVMValueRef LLVMExtDIBuilderInsertDeclareAtEnd(
 }
 
 LLVMMetadataRef LLVMExtDIBuilderCreateExpression(
-    DIBuilderRef Dref, int64_t *Addr, size_t Length) {
-  return wrap(Dref->createExpression(ArrayRef<int64_t>(Addr, Length)));
+    DIBuilderRef Dref, uint64_t *Addr, size_t Length) {
+  return wrap(Dref->createExpression(ArrayRef<uint64_t>(Addr, Length)));
 }
 
 LLVMMetadataRef LLVMExtDIBuilderCreateEnumerationType(
@@ -587,8 +587,12 @@ LLVMBool LLVMExtCreateMCJITCompilerForModule(
     for (auto &F : *Mod) {
       auto Attrs = F.getAttributes();
       StringRef Value = options.NoFramePointerElim ? "all" : "none";
-      Attrs = Attrs.addAttribute(F.getContext(), AttributeList::FunctionIndex,
-                                 "frame-pointer", Value);
+      #if LLVM_VERSION_GE(14, 0)
+        Attrs = Attrs.addFnAttribute(F.getContext(), "frame-pointer", Value);
+      #else
+        Attrs = Attrs.addAttribute(F.getContext(), AttributeList::FunctionIndex,
+                                   "frame-pointer", Value);
+      #endif
       F.setAttributes(Attrs);
     }
 
diff --git a/src/llvm/lib_llvm.cr b/src/llvm/lib_llvm.cr
index d22e00b59fe2..5e5811d8ec2a 100644
--- a/src/llvm/lib_llvm.cr
+++ b/src/llvm/lib_llvm.cr
@@ -19,6 +19,7 @@ end
 
 {% begin %}
   lib LibLLVM
+    IS_140 = {{LibLLVM::VERSION.starts_with?("14.0")}}
     IS_130 = {{LibLLVM::VERSION.starts_with?("13.0")}}
     IS_120 = {{LibLLVM::VERSION.starts_with?("12.0")}}
     IS_111 = {{LibLLVM::VERSION.starts_with?("11.1")}}
diff --git a/src/llvm/lib_llvm_ext.cr b/src/llvm/lib_llvm_ext.cr
index 4f5aa4b39982..59dd50c02c13 100644
--- a/src/llvm/lib_llvm_ext.cr
+++ b/src/llvm/lib_llvm_ext.cr
@@ -65,7 +65,7 @@ lib LibLLVMExt
                                                                             block : LibLLVM::BasicBlockRef) : LibLLVM::ValueRef
 
   fun di_builder_create_expression = LLVMExtDIBuilderCreateExpression(builder : DIBuilder,
-                                                                      addr : Int64*, length : SizeT) : LibLLVM::MetadataRef
+                                                                      addr : UInt64*, length : SizeT) : LibLLVM::MetadataRef
 
   fun di_builder_get_or_create_array = LLVMExtDIBuilderGetOrCreateArray(builder : DIBuilder, data : LibLLVM::MetadataRef*, length : SizeT) : LibLLVM::MetadataRef
   fun di_builder_create_enumerator = LLVMExtDIBuilderCreateEnumerator(builder : DIBuilder, name : Char*, value : Int64) : LibLLVM::MetadataRef