diff --git a/Include/internal/pycore_token.h b/Include/internal/pycore_token.h
index 571cd6249f2812..8e1f8aef59ad3b 100644
--- a/Include/internal/pycore_token.h
+++ b/Include/internal/pycore_token.h
@@ -93,6 +93,8 @@ extern "C" {
 #define ISSTRINGLIT(x)          ((x) == STRING           || \
                                  (x) == FSTRING_MIDDLE)
 
+#define GENERATE_2CHAR_CODE(x, y) ((int)((x) << 8 | (y))) // Generate a 16-bit integer from 2 8-bit characters
+#define GENERATE_3CHAR_CODE(x, y, z) ((int)((x) << 16 | (y) << 8 | (z))) // Generate a 24-bit integer from 3 8-bit characters
 
 // Export these 4 symbols for 'test_peg_generator'
 PyAPI_DATA(const char * const) _PyParser_TokenNames[]; /* Token names */
diff --git a/Parser/token.c b/Parser/token.c
index 4f163f21609a0a..609d484840cb82 100644
--- a/Parser/token.c
+++ b/Parser/token.c
@@ -81,30 +81,30 @@ int
 _PyToken_OneChar(int c1)
 {
     switch (c1) {
-    case '!': return EXCLAMATION;
-    case '%': return PERCENT;
-    case '&': return AMPER;
-    case '(': return LPAR;
-    case ')': return RPAR;
-    case '*': return STAR;
-    case '+': return PLUS;
-    case ',': return COMMA;
-    case '-': return MINUS;
-    case '.': return DOT;
-    case '/': return SLASH;
-    case ':': return COLON;
-    case ';': return SEMI;
-    case '<': return LESS;
-    case '=': return EQUAL;
-    case '>': return GREATER;
-    case '@': return AT;
-    case '[': return LSQB;
-    case ']': return RSQB;
-    case '^': return CIRCUMFLEX;
-    case '{': return LBRACE;
-    case '|': return VBAR;
-    case '}': return RBRACE;
-    case '~': return TILDE;
+        case '!': return EXCLAMATION;
+        case '%': return PERCENT;
+        case '&': return AMPER;
+        case '(': return LPAR;
+        case ')': return RPAR;
+        case '*': return STAR;
+        case '+': return PLUS;
+        case ',': return COMMA;
+        case '-': return MINUS;
+        case '.': return DOT;
+        case '/': return SLASH;
+        case ':': return COLON;
+        case ';': return SEMI;
+        case '<': return LESS;
+        case '=': return EQUAL;
+        case '>': return GREATER;
+        case '@': return AT;
+        case '[': return LSQB;
+        case ']': return RSQB;
+        case '^': return CIRCUMFLEX;
+        case '{': return LBRACE;
+        case '|': return VBAR;
+        case '}': return RBRACE;
+        case '~': return TILDE;
     }
     return OP;
 }
@@ -112,83 +112,27 @@ _PyToken_OneChar(int c1)
 int
 _PyToken_TwoChars(int c1, int c2)
 {
-    switch (c1) {
-    case '!':
-        switch (c2) {
-        case '=': return NOTEQUAL;
-        }
-        break;
-    case '%':
-        switch (c2) {
-        case '=': return PERCENTEQUAL;
-        }
-        break;
-    case '&':
-        switch (c2) {
-        case '=': return AMPEREQUAL;
-        }
-        break;
-    case '*':
-        switch (c2) {
-        case '*': return DOUBLESTAR;
-        case '=': return STAREQUAL;
-        }
-        break;
-    case '+':
-        switch (c2) {
-        case '=': return PLUSEQUAL;
-        }
-        break;
-    case '-':
-        switch (c2) {
-        case '=': return MINEQUAL;
-        case '>': return RARROW;
-        }
-        break;
-    case '/':
-        switch (c2) {
-        case '/': return DOUBLESLASH;
-        case '=': return SLASHEQUAL;
-        }
-        break;
-    case ':':
-        switch (c2) {
-        case '=': return COLONEQUAL;
-        }
-        break;
-    case '<':
-        switch (c2) {
-        case '<': return LEFTSHIFT;
-        case '=': return LESSEQUAL;
-        case '>': return NOTEQUAL;
-        }
-        break;
-    case '=':
-        switch (c2) {
-        case '=': return EQEQUAL;
-        }
-        break;
-    case '>':
-        switch (c2) {
-        case '=': return GREATEREQUAL;
-        case '>': return RIGHTSHIFT;
-        }
-        break;
-    case '@':
-        switch (c2) {
-        case '=': return ATEQUAL;
-        }
-        break;
-    case '^':
-        switch (c2) {
-        case '=': return CIRCUMFLEXEQUAL;
-        }
-        break;
-    case '|':
-        switch (c2) {
-        case '=': return VBAREQUAL;
-        }
-        break;
+    switch (GENERATE_2CHAR_CODE(c1, c2)) {
+        case GENERATE_2CHAR_CODE('!', '='): return NOTEQUAL;
+        case GENERATE_2CHAR_CODE('%', '='): return PERCENTEQUAL;
+        case GENERATE_2CHAR_CODE('&', '='): return AMPEREQUAL;
+        case GENERATE_2CHAR_CODE('*', '*'): return DOUBLESTAR;
+        case GENERATE_2CHAR_CODE('*', '='): return STAREQUAL;
+        case GENERATE_2CHAR_CODE('+', '='): return PLUSEQUAL;
+        case GENERATE_2CHAR_CODE('-', '='): return MINEQUAL;
+        case GENERATE_2CHAR_CODE('-', '>'): return RARROW;
+        case GENERATE_2CHAR_CODE('/', '/'): return DOUBLESLASH;
+        case GENERATE_2CHAR_CODE('/', '='): return SLASHEQUAL;
+        case GENERATE_2CHAR_CODE(':', '='): return COLONEQUAL;
+        case GENERATE_2CHAR_CODE('<', '<'): return LEFTSHIFT;
+        case GENERATE_2CHAR_CODE('<', '='): return LESSEQUAL;
+        case GENERATE_2CHAR_CODE('<', '>'): return NOTEQUAL;
+        case GENERATE_2CHAR_CODE('=', '='): return EQEQUAL;
+        case GENERATE_2CHAR_CODE('>', '='): return GREATEREQUAL;
+        case GENERATE_2CHAR_CODE('>', '>'): return RIGHTSHIFT;
+        case GENERATE_2CHAR_CODE('@', '='): return ATEQUAL;
+        case GENERATE_2CHAR_CODE('^', '='): return CIRCUMFLEXEQUAL;
+        case GENERATE_2CHAR_CODE('|', '='): return VBAREQUAL;
     }
     return OP;
 }
@@ -196,52 +140,12 @@ _PyToken_TwoChars(int c1, int c2)
 int
 _PyToken_ThreeChars(int c1, int c2, int c3)
 {
-    switch (c1) {
-    case '*':
-        switch (c2) {
-        case '*':
-            switch (c3) {
-            case '=': return DOUBLESTAREQUAL;
-            }
-            break;
-        }
-        break;
-    case '.':
-        switch (c2) {
-        case '.':
-            switch (c3) {
-            case '.': return ELLIPSIS;
-            }
-            break;
-        }
-        break;
-    case '/':
-        switch (c2) {
-        case '/':
-            switch (c3) {
-            case '=': return DOUBLESLASHEQUAL;
-            }
-            break;
-        }
-        break;
-    case '<':
-        switch (c2) {
-        case '<':
-            switch (c3) {
-            case '=': return LEFTSHIFTEQUAL;
-            }
-            break;
-        }
-        break;
-    case '>':
-        switch (c2) {
-        case '>':
-            switch (c3) {
-            case '=': return RIGHTSHIFTEQUAL;
-            }
-            break;
-        }
-        break;
+    switch (GENERATE_3CHAR_CODE(c1, c2, c3)) {
+        case GENERATE_3CHAR_CODE('*', '*', '='): return DOUBLESTAREQUAL;
+        case GENERATE_3CHAR_CODE('.', '.', '.'): return ELLIPSIS;
+        case GENERATE_3CHAR_CODE('/', '/', '='): return DOUBLESLASHEQUAL;
+        case GENERATE_3CHAR_CODE('<', '<', '='): return LEFTSHIFTEQUAL;
+        case GENERATE_3CHAR_CODE('>', '>', '='): return RIGHTSHIFTEQUAL;
     }
     return OP;
 }
diff --git a/Tools/build/generate_token.py b/Tools/build/generate_token.py
index 16c38841e44a4d..5b8d1c331fe277 100755
--- a/Tools/build/generate_token.py
+++ b/Tools/build/generate_token.py
@@ -83,6 +83,8 @@ def update_file(file, content):
 #define ISSTRINGLIT(x)          ((x) == STRING           || \\
                                  (x) == FSTRING_MIDDLE)
 
+#define GENERATE_2CHAR_CODE(x, y) ((int)((x) << 8 | (y))) // Generate a 16-bit integer from 2 8-bit characters
+#define GENERATE_3CHAR_CODE(x, y, z) ((int)((x) << 16 | (y) << 8 | (z))) // Generate a 24-bit integer from 3 8-bit characters
 
 // Export these 4 symbols for 'test_peg_generator'
 PyAPI_DATA(const char * const) _PyParser_TokenNames[]; /* Token names */
@@ -149,6 +151,31 @@ def make_h(infile, outfile='Include/internal/pycore_token.h'):
 }
 """
 
+def generate_one_char_tokens(tokens):
+    result = []
+    result.append('    switch (c1) {\n')
+    for c, name in sorted(tokens.items()):
+        result.append("        case '%s': return %s;\n" % (c, name))
+    result.append('    }\n')
+    return ''.join(result)
+
+def generate_two_char_tokens(tokens):
+    result = []
+    result.append('    switch (GENERATE_2CHAR_CODE(c1, c2)) {\n')
+    for (c1, c2), name in sorted(tokens.items()):
+        result.append("        case GENERATE_2CHAR_CODE('%s', '%s'): return %s;\n" % (c1, c2, name))
+    result.append('    }\n')
+    return ''.join(result)
+
+def generate_three_char_tokens(tokens):
+    result = []
+    result.append('    switch (GENERATE_3CHAR_CODE(c1, c2, c3)) {\n')
+    for (c1, c2, c3), name in sorted(tokens.items()):
+        result.append("        case GENERATE_3CHAR_CODE('%s', '%s', '%s'): return %s;\n" % (c1, c2, c3, name))
+    result.append('    }\n')
+    return ''.join(result)
+
+
 def generate_chars_to_token(mapping, n=1):
     result = []
     write = result.append
@@ -172,14 +199,15 @@ def generate_chars_to_token(mapping, n=1):
 def make_c(infile, outfile='Parser/token.c'):
     tok_names, ERRORTOKEN, string_to_tok = load_tokens(infile)
     string_to_tok['<>'] = string_to_tok['!=']
-    chars_to_token = {}
+    chars_to_token = {
+        1: {},
+        2: {},
+        3: {},
+    }
     for string, value in string_to_tok.items():
         assert 1 <= len(string) <= 3
         name = tok_names[value]
-        m = chars_to_token.setdefault(len(string), {})
-        for c in string[:-1]:
-            m = m.setdefault(c, {})
-        m[string[-1]] = name
+        chars_to_token[len(string)][string] = name
 
     names = []
     for value, name in enumerate(tok_names):
@@ -190,9 +218,9 @@ def make_c(infile, outfile='Parser/token.c'):
 
     if update_file(outfile, token_c_template % (
             ''.join(names),
-            generate_chars_to_token(chars_to_token[1]),
-            generate_chars_to_token(chars_to_token[2]),
-            generate_chars_to_token(chars_to_token[3])
+            generate_one_char_tokens(chars_to_token[1]),
+            generate_two_char_tokens(chars_to_token[2]),
+            generate_three_char_tokens(chars_to_token[3])
         )):
         print("%s regenerated from %s" % (outfile, infile))