Get the same input multiple times in python tkinter?

Behavior of your program is a bit unclear for me, but I try to help.

First solution: show tkinter askstring dialog num times. You can break for loop if user press Cancel button. It's not exactly what you want, but it's very easy to implement:

from tkinter import *import tkinter.simpledialog as simpledialogdef add_users():    n = simpledialog.askinteger('', 'How many users are you going to put in?', initialvalue=1, minvalue=1, maxvalue=10)    if not n: # 'Cancel'        return    for i in range(n):        user = simpledialog.askstring('', 'User #%s from #%s' % (i+1, n))        if user is None: # 'Cancel'            return        # Do something useful        print(user)root = Tk()Button(root, text='Add users', command=add_users).pack(padx=50, pady=50)Button(root, text='Quit', command=root.destroy).pack(pady=30)root.mainloop()

Second (if you want to put entry and all new names to window with quit button):

from tkinter import *import tkinter.simpledialog as simpledialogclass YourApp():    def __init__(self):        self.root = Tk()        Button(self.root, text='Quit', command=self.root.destroy).pack(pady=20)        self.ask_button = Button(self.root, text='Add users', command=self.add_users)        self.ask_button.pack(padx=50, pady=50)        self.root.mainloop()    def add_users(self):        self.users_count = 0        self.user_name = StringVar()        self.frame = Frame(self.root)        self.frame.pack()        self.users_count = simpledialog.askinteger('', 'How many users are you going to put in?', initialvalue=1, minvalue=1, maxvalue=10)        self.user_entry = Entry(self.frame, textvariable=self.user_name)        self.user_entry.pack(pady=10)        self.user_entry.bind('<Key-Return>', self.on_new_user)        self.user_entry.focus_set()    def on_new_user(self, event):        # your code        print(self.user_name.get())        Label(self.frame, text='User Inputted: %s' % self.user_name.get()).pack()        self.users_count -= 1        if not self.users_count:            self.user_entry.destroy()        self.user_name.set('')YourApp()

There are three geometry managers in Tkinter: place (it's very similar to canvas in your case), grid and pack.Canvas usually used for drawing pictures or graphs.