from tkinter import * import webbrowser def weblink(*args): index = lb.curselection()[0] item = lb.get(index) if 'https://' in item: webbrowser.open_new(item) root = Tk() lb = Listbox(root) lb.bind('<>', weblink) for item in list_of_items: lb.insert(END, item) lb.pack() root.mainloop()