Most of the hotels in downtown Chicago are pricey but dog friendly and a lot of the downtown cafes and restaurants with outside tables are dog friendly. If you are close to the pier or can get down there, it's a good place to walk your dog and take photos of the lake etc. A lot of shops down there will let you come in with your pups as long as your dog is in a carrier. Have a safe trip.
BTW-There's a Pet place that was suppose to open on 55th that has a brand new pet hotel that someone was telling me about. It has a Petco attached to it. I'll ask around.