I was going to suggest Hyatt at McCormick Place, (Greater Chicago zone) but after checking the convention schedule, feel your chance of getting a good deal is not likely due to that : http://www.chicago.il.org/smi/calendar.cfm You most likely need to split your stays into 2 or more bids. Unless you must stay in NMA or River North or Loop, you may actually get some very good deals at North Shore area. Hyatt Deerfield is conveniently located less than a mile on the same road of the Milwaukee District North Line train station on Lake Cook Road. They have free shuttle to the station and from there it is about 50 minutes train ride right into town. http://metrarail.com/Sched/md_n/mdn_wki.shtml This Hyatt while it is a 3*, it is newer and nicer than the Hyatt Regency at NMA. It is a low rise hotel. And you can have it for $34 - $35 !!! The other hotel shows up at Deerfield is Marriott Suites. But recently it is mostly Hyatt Deerfield. Oh, if you split the stays between you and wifey, and if you get the Hyatt, you will earn a free night for each 2 stays you do up till 09/30. The free nights earned can be used till 11/30. You do need to join Goldpassport (Hyatt's frequent guest program), register for the Faster Free Night promo, charge some incidentals such as a drink, a dessert, etc to your room and pay by Mastercard. The free night earned can be used anywhere in the world in the whole Hyatt system. A marvelous deal.