Walmart has the SwissGear SA5320 16.5" Messenger Bag (Gray or Blue) for $14 + $6 shipping fee = $20 shipped. Free shipping on $35+. It features a 13" padded laptop pocket, mesh organizer panel, and two side mesh bottle pockets.
eBay has the Samsonite 20" Bartlett Upright Spinner Luggage (62251XXXX) for $56 - $14 off in cart = $42 with free shipping. Also get in 24" for $53 and in 29" for $64.
Amazon has the 2-Piece Travelpro TourGo Softside Lightweight Luggage Set (Black) for $50 with free shipping. Retail price: $410. Set includes one carry on expandable softside spinner that meets carry on sizer bin restrictions for most domestic airlines and one checked medium expandable softside spinner.
Has excellent Amazon Reviews.