The Allegro is a Kimpton hotel, a very well-run chain with good amenities. I've stayed at Kimptons in Chicao (but not the Allegro) and DC and have never been disappointed. If you join Kimpton InTouch (free), the hotel is likely to allow free in-room wi-fi even though you booked through Hotwire. No offense to Aaron, but the Allegro is in the far west (northwest, actually) part of the Loop--not in the neighborhood called the West Loop. It's on Randolph between LaSalle and Wells. That places it about a half mile to Millenium Park or the lower end of Mag Mile shopping, and about 1½ miles to the Hancock Building or Navy Pier. Wrigley Field, Chinatown, or Lincoln Park are easy rides on the El (or bus, if you prefer). Estimate the number of public transportation rides you'll be taking; that'll give you a good idea whether the three-day pass is worth it. Remember, it's $20 per person. Either way, it's good to get your Ventra card ahead of time. All the info you need is on, or linked to from, the CTA web site. Re nickel and dime-ing, as you mentioned, Chicago is a big city, with lots of business travelers, so if you stay downtown (vs. the suburbs), yeah, it'll be harder, but not completely impossible, to locate those free services. For example, the Blackstone Renaissance on S. Michigan Ave, where I stayed last time (via BB/Hotwire), offers free wi-fi. And in many (most?) places that charge, there's free wi-fi in the lobby or other public area. Some places do offer a free breakfast; Embassy Suites, which can appear on Hotwire, is one. Parking, well, that's another matter. Occasionally you might spot a parking-included (or reduced-fee) deal on Travelzoo or the like, but generally it's just something you need to figure in to your total cost if you want to stay anywhere in or near downtown. The only free parking I know of in that area is the HoJo in River North. Are you driving there? If so, I can post a couple of links to Chicago parking information, plus clue you in to a couple of places I tend to use--depending on where you'll be staying, of course. Also, as you know, where to go for deep dish pizza is a matter of furious debate. Do you have a place or two picked out? Regarding other food, if you'd like some input, post what kind of food you'd prefer and I'd be glad to offer some suggestions, as would others, I'm sure.