diff --git a/python/hopsworks/core/dataset_api.py b/python/hopsworks/core/dataset_api.py
index abd20a256..4893e2dc1 100644
--- a/python/hopsworks/core/dataset_api.py
+++ b/python/hopsworks/core/dataset_api.py
@@ -16,13 +16,24 @@
 
 import math
 import os
+import time
 from tqdm.auto import tqdm
 import shutil
 import logging
+import copy
 
 from hopsworks import client
 from hopsworks.client.exceptions import RestAPIError
 from hopsworks.client.exceptions import DatasetException
+from concurrent.futures import ThreadPoolExecutor, wait
+
+
+class Chunk:
+    def __init__(self, content, number, status):
+        self.content = content
+        self.number = number
+        self.status = status
+        self.retries = 0
 
 
 class DatasetApi:
@@ -33,7 +44,7 @@ def __init__(
         self._project_id = project_id
         self._log = logging.getLogger(__name__)
 
-    DEFAULT_FLOW_CHUNK_SIZE = 1048576
+    FLOW_PERMANENT_ERRORS = [404, 413, 415, 500, 501]
 
     def download(self, path: str, local_path: str = None, overwrite: bool = False):
         """Download file from Hopsworks Filesystem to the current working directory.
@@ -126,7 +137,16 @@ def download(self, path: str, local_path: str = None, overwrite: bool = False):
 
         return local_path
 
-    def upload(self, local_path: str, upload_path: str, overwrite: bool = False):
+    def upload(
+        self,
+        local_path: str,
+        upload_path: str,
+        overwrite: bool = False,
+        chunk_size=1048576,
+        simultaneous_uploads=3,
+        max_chunk_retries=1,
+        chunk_retry_interval=1,
+    ):
         """Upload a file to the Hopsworks filesystem.
 
         ```python
@@ -144,6 +164,10 @@ def upload(self, local_path: str, upload_path: str, overwrite: bool = False):
             local_path: local path to file to upload
             upload_path: path to directory where to upload the file in Hopsworks Filesystem
             overwrite: overwrite file if exists
+            chunk_size: upload chunk size in bytes. Default 1048576 bytes
+            simultaneous_uploads: number of simultaneous chunks to upload. Default 3
+            max_chunk_retries: maximum retry for a chunk. Default is 1
+            chunk_retry_interval: chunk retry interval in seconds. Default is 1sec
         # Returns
             `str`: Path to uploaded file
         # Raises
@@ -171,9 +195,11 @@ def upload(self, local_path: str, upload_path: str, overwrite: bool = False):
                     )
                 )
 
-        num_chunks = math.ceil(file_size / self.DEFAULT_FLOW_CHUNK_SIZE)
+        num_chunks = math.ceil(file_size / chunk_size)
 
-        base_params = self._get_flow_base_params(file_name, num_chunks, file_size)
+        base_params = self._get_flow_base_params(
+            file_name, num_chunks, file_size, chunk_size
+        )
 
         chunk_number = 1
         with open(local_path, "rb") as f:
@@ -187,21 +213,41 @@ def upload(self, local_path: str, upload_path: str, overwrite: bool = False):
             except Exception:
                 self._log.exception("Failed to initialize progress bar.")
                 self._log.info("Starting upload")
-
-            while True:
-                chunk = f.read(self.DEFAULT_FLOW_CHUNK_SIZE)
-                if not chunk:
-                    break
-
-                query_params = base_params
-                query_params["flowCurrentChunkSize"] = len(chunk)
-                query_params["flowChunkNumber"] = chunk_number
-
-                self._upload_request(query_params, upload_path, file_name, chunk)
-                chunk_number += 1
-
-                if pbar is not None:
-                    pbar.update(query_params["flowCurrentChunkSize"])
+            with ThreadPoolExecutor(simultaneous_uploads) as executor:
+                while True:
+                    chunks = []
+                    for _ in range(simultaneous_uploads):
+                        chunk = f.read(chunk_size)
+                        if not chunk:
+                            break
+                        chunks.append(Chunk(chunk, chunk_number, "pending"))
+                        chunk_number += 1
+
+                    if len(chunks) == 0:
+                        break
+
+                    # upload each chunk and update pbar
+                    futures = [
+                        executor.submit(
+                            self._upload_chunk,
+                            base_params,
+                            upload_path,
+                            file_name,
+                            chunk,
+                            pbar,
+                            max_chunk_retries,
+                            chunk_retry_interval,
+                        )
+                        for chunk in chunks
+                    ]
+                    # wait for all upload tasks to complete
+                    _, _ = wait(futures)
+                    try:
+                        _ = [future.result() for future in futures]
+                    except Exception as e:
+                        if pbar is not None:
+                            pbar.close()
+                        raise e
 
             if pbar is not None:
                 pbar.close()
@@ -210,10 +256,47 @@ def upload(self, local_path: str, upload_path: str, overwrite: bool = False):
 
         return upload_path + "/" + os.path.basename(local_path)
 
-    def _get_flow_base_params(self, file_name, num_chunks, size):
+    def _upload_chunk(
+        self,
+        base_params,
+        upload_path,
+        file_name,
+        chunk: Chunk,
+        pbar,
+        max_chunk_retries,
+        chunk_retry_interval,
+    ):
+        query_params = copy.copy(base_params)
+        query_params["flowCurrentChunkSize"] = len(chunk.content)
+        query_params["flowChunkNumber"] = chunk.number
+
+        chunk.status = "uploading"
+        while True:
+            try:
+                self._upload_request(
+                    query_params, upload_path, file_name, chunk.content
+                )
+                break
+            except RestAPIError as re:
+                chunk.retries += 1
+                if (
+                    re.response.status_code in DatasetApi.FLOW_PERMANENT_ERRORS
+                    or chunk.retries > max_chunk_retries
+                ):
+                    chunk.status = "failed"
+                    raise re
+                time.sleep(chunk_retry_interval)
+                continue
+
+        chunk.status = "uploaded"
+
+        if pbar is not None:
+            pbar.update(query_params["flowCurrentChunkSize"])
+
+    def _get_flow_base_params(self, file_name, num_chunks, size, chunk_size):
         return {
             "templateId": -1,
-            "flowChunkSize": self.DEFAULT_FLOW_CHUNK_SIZE,
+            "flowChunkSize": chunk_size,
             "flowTotalSize": size,
             "flowIdentifier": str(size) + "_" + file_name,
             "flowFilename": file_name,