Avber via Amazon offers the Avber Women's Vintage Messenger Bag in Brown, Blue, or Purple for $39.99. Coupon code "LEOP3V8F" cuts the price to $27.99. With free shipping, that's up to $102 off and the lowest total price we could find. It includes a removable strap, multiple inner pockets, and a twist lock. It can can accomodate iPad mini or 10" notebook.
6pm offers the Coach Women's Bleecker Soft Port Duffle Handbag in Red Currant for $214.99 with free shipping. That's $143 off list and the lowest total price we could find. It features inside zip, cell phone, and multifunction pockets and a top zip closure.
Update: It's now available in Black for $179.99 with free shipping.