diff --git a/src/expr.rs b/src/expr.rs
index c15e680333b..25226991fbc 100644
--- a/src/expr.rs
+++ b/src/expr.rs
@@ -1842,11 +1842,14 @@ fn rewrite_let(
 ) -> Option<String> {
     let mut result = "let ".to_owned();
 
+    // TODO(ytmimi) comments could appear between `let` and the `pat`
+
     // 4 = "let ".len()
     let pat_shape = shape.offset_left(4)?;
     let pat_str = pat.rewrite(context, pat_shape)?;
     result.push_str(&pat_str);
 
+    // TODO(ytmimi) comments could appear between `pat` and `=`
     result.push_str(" =");
 
     let comments_lo = context
diff --git a/src/pairs.rs b/src/pairs.rs
index 96f023b3b0e..9dac20d3699 100644
--- a/src/pairs.rs
+++ b/src/pairs.rs
@@ -42,9 +42,13 @@ pub(crate) fn rewrite_all_pairs(
     context: &RewriteContext<'_>,
 ) -> Option<String> {
     expr.flatten(context, shape).and_then(|list| {
-        // First we try formatting on one line.
-        rewrite_pairs_one_line(&list, shape, context)
-            .or_else(|| rewrite_pairs_multiline(&list, shape, context))
+        if list.let_chain_count() > 0 && !list.can_rewrite_let_chain_single_line() {
+            rewrite_pairs_multiline(&list, shape, context)
+        } else {
+            // First we try formatting on one line.
+            rewrite_pairs_one_line(&list, shape, context)
+                .or_else(|| rewrite_pairs_multiline(&list, shape, context))
+        }
     })
 }
 
@@ -255,6 +259,37 @@ struct PairList<'a, 'b, T: Rewrite> {
     separators: Vec<&'a str>,
 }
 
+fn is_ident(expr: &ast::Expr) -> bool {
+    match &expr.kind {
+        ast::ExprKind::Path(None, path) if path.segments.len() == 1 => true,
+        ast::ExprKind::Unary(_, expr)
+        | ast::ExprKind::AddrOf(_, _, expr)
+        | ast::ExprKind::Paren(expr)
+        | ast::ExprKind::Try(expr) => is_ident(expr),
+        _ => false,
+    }
+}
+
+impl<'a, 'b> PairList<'a, 'b, ast::Expr> {
+    fn let_chain_count(&self) -> usize {
+        self.list
+            .iter()
+            .filter(|(expr, _)| matches!(expr.kind, ast::ExprKind::Let(_, _, _)))
+            .count()
+    }
+
+    fn can_rewrite_let_chain_single_line(&self) -> bool {
+        if self.list.len() != 2 {
+            return false;
+        }
+
+        let fist_item_is_ident = is_ident(self.list[0].0);
+        let second_item_is_let_chain = matches!(self.list[1].0.kind, ast::ExprKind::Let(_, _, _));
+
+        fist_item_is_ident && second_item_is_let_chain
+    }
+}
+
 impl FlattenPair for ast::Expr {
     fn flatten(
         &self,
diff --git a/tests/source/let_chains.rs b/tests/source/let_chains.rs
index f5f8285aa10..88ee126bfbd 100644
--- a/tests/source/let_chains.rs
+++ b/tests/source/let_chains.rs
@@ -13,4 +13,109 @@ fn main() {
 
     if let XXXXXXXXX { xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx, yyyyyyyyyyyyy, zzzzzzzzzzzzz} = xxxxxxx()
     && let Foo = bar() { todo!() }
-}
\ No newline at end of file
+}
+
+fn test_single_line_let_chain() {
+    // first item in let-chain is an ident
+    if a && let Some(b) = foo() {
+    }
+
+    // first item in let-chain is a unary ! with an ident
+    let unary_not = if !from_hir_call
+        && let Some(p) = parent
+    {
+    };
+
+    // first item in let-chain is a unary * with an ident
+    let unary_deref = if *some_deref
+        && let Some(p) = parent
+    {
+    };
+
+    // first item in let-chain is a unary - (neg) with an ident
+    let unary_neg = if -some_ident
+        && let Some(p) = parent
+    {
+    };
+
+    // first item in let-chain is a try (?) with an ident
+    let try_ = if some_try?
+        && let Some(p) = parent
+    {
+    };
+
+    // first item in let-chain is an ident wrapped in parens
+    let in_parens = if (some_ident)
+        && let Some(p) = parent
+    {
+    };
+
+    // first item in let-chain is a ref & with an ident
+    let _ref = if &some_ref
+        && let Some(p) = parent
+    {
+    };
+
+    // first item in let-chain is a ref &mut with an ident
+    let mut_ref = if &mut some_ref
+        && let Some(p) = parent
+    {
+    };
+
+    // chain unary ref and try
+    let chain_of_unary_ref_and_try = if !&*some_ref?
+        && let Some(p) = parent {
+    };
+}
+
+fn test_multi_line_let_chain() {
+    // Can only single line the let-chain if the first item is an ident
+    if let Some(x) = y && a {
+
+    }
+
+    // More than one let-chain must be formatted on multiple lines
+    if let Some(x) = y && let Some(a) = b {
+
+    }
+
+    // The ident isn't long enough so we don't wrap the first let-chain
+    if a && let Some(x) = y && let Some(a) = b {
+
+    }
+
+    // The ident is long enough so both let-chains are wrapped
+    if aaa && let Some(x) = y && let Some(a) = b {
+
+    }
+
+    // function call
+    if a() && let Some(x) = y {
+
+    }
+
+    // bool literal
+    if true && let Some(x) = y {
+
+    }
+
+    // cast to a bool
+    if 1 as bool && let Some(x) = y {
+
+    }
+
+    // matches! macro call
+    if matches!(a, some_type) && let Some(x) = y {
+
+    }
+
+    // block expression returning bool
+    if { true } && let Some(x) = y {
+
+    }
+
+    // field access
+    if a.x && let Some(x) = y {
+
+    }
+}
diff --git a/tests/target/let_chains.rs b/tests/target/let_chains.rs
index 36fd0ba1590..165641521cf 100644
--- a/tests/target/let_chains.rs
+++ b/tests/target/let_chains.rs
@@ -1,5 +1,7 @@
 fn main() {
-    if let x = x && x {}
+    if let x = x
+        && x
+    {}
 
     if xxx && let x = x {}
 
@@ -12,7 +14,10 @@ fn main() {
     {}
 
     if aaaaaaaaaaaaaaaaaaaaa && aaaaaaaaaaaaaaa
-        || aaaaaaaaa && let Some(x) = xxxxxxxxxxxx && aaaaaaa && let None = aaaaaaaaaa
+        || aaaaaaaaa
+            && let Some(x) = xxxxxxxxxxxx
+            && aaaaaaa
+            && let None = aaaaaaaaaa
     {}
 
     if let Some(Struct { x: TS(1, 2) }) = path::to::<_>(hehe)
@@ -39,3 +44,85 @@ fn main() {
         todo!()
     }
 }
+
+fn test_single_line_let_chain() {
+    // first item in let-chain is an ident
+    if a && let Some(b) = foo() {}
+
+    // first item in let-chain is a unary ! with an ident
+    let unary_not = if !from_hir_call && let Some(p) = parent {};
+
+    // first item in let-chain is a unary * with an ident
+    let unary_deref = if *some_deref && let Some(p) = parent {};
+
+    // first item in let-chain is a unary - (neg) with an ident
+    let unary_neg = if -some_ident && let Some(p) = parent {};
+
+    // first item in let-chain is a try (?) with an ident
+    let try_ = if some_try? && let Some(p) = parent {};
+
+    // first item in let-chain is an ident wrapped in parens
+    let in_parens = if (some_ident) && let Some(p) = parent {};
+
+    // first item in let-chain is a ref & with an ident
+    let _ref = if &some_ref && let Some(p) = parent {};
+
+    // first item in let-chain is a ref &mut with an ident
+    let mut_ref = if &mut some_ref && let Some(p) = parent {};
+
+    // chain unary ref and try
+    let chain_of_unary_ref_and_try = if !&*some_ref? && let Some(p) = parent {};
+}
+
+fn test_multi_line_let_chain() {
+    // Can only single line the let-chain if the first item is an ident
+    if let Some(x) = y
+        && a
+    {}
+
+    // More than one let-chain must be formatted on multiple lines
+    if let Some(x) = y
+        && let Some(a) = b
+    {}
+
+    // The ident isn't long enough so we don't wrap the first let-chain
+    if a && let Some(x) = y
+        && let Some(a) = b
+    {}
+
+    // The ident is long enough so both let-chains are wrapped
+    if aaa
+        && let Some(x) = y
+        && let Some(a) = b
+    {}
+
+    // function call
+    if a()
+        && let Some(x) = y
+    {}
+
+    // bool literal
+    if true
+        && let Some(x) = y
+    {}
+
+    // cast to a bool
+    if 1 as bool
+        && let Some(x) = y
+    {}
+
+    // matches! macro call
+    if matches!(a, some_type)
+        && let Some(x) = y
+    {}
+
+    // block expression returning bool
+    if { true }
+        && let Some(x) = y
+    {}
+
+    // field access
+    if a.x
+        && let Some(x) = y
+    {}
+}