So your plan is two rooms and five people? So 2 people sharing a bed in one room, then 2 people sharing a bed plus one more person on a rollaway in the second? (Or, I suppose, two real beds in the second room would work also.) I think your odds of getting the rollaway are about the same in either Loop or NMA. And those odds are probably "ok"... maybe 60/40? But that's just a guess, knowing the hotels. The larger ones that come up more often also often have smaller "priceline" rooms. A lot of it is a function of how early you can check in and how well you treat the desk clerk. Have you checked hotwire, telling it you want two rooms and a total of five people? That will guarantee you the rollaway. Have you seriously considered staying in Evanston, tho? It's a great town. If you're thinking of the Hilton Garden Inn, it's a very nice hotel from everything I've heard. Same with the Orrington, which was recently renovated. The HGI is in the middle of a three+ block entertainment zone -- very nice movie theatre, book store, many excellent restaurants, etc. The parking is much cheaper in Evanston, if you're driving. As I recall, outside of about an eight block radius of the center of downtown, overnight street parking becomes free. The HGI is a block from the L purple line and Metra stations. This gives you two affordable and relatively fast ways (45 minutes) to get downtown. And, obviously, if you're reserving direct you have more better control over what you're getting. Think about it. (Also note, rates downtown for your stay are very high, with the two big Loop hotels (Hilton Chicago and Palmer House) both showing sold out for at least part of your stay.)