If you want to go to Water Tower, then I would go with the Whitehall deal on easyclicktravel. The Whitehall is literally two blocks from WT and 1 block from Hancock Observatory and a couple of blocks from 900 N. Michigan Mall. Plus, there is an subway station not far away on Chicago and State if you want a quick way to get into the downtown/loop area. It does get some mixed reviews, but $119 regular rate from EasyClickTravel is about $30-40 less than regular rate everywhere else, and the location is first-rate. I definitely know where you're coming from in regards to dust/smoke allergies. The only time I've ever had a bad issue was at the W City Center, which was an otherwise nice hotel. The majority of the room wasn't dusty, but the corners (behind the bed, etc) looked like they hadn't been dusted in ages. If you have an allergy problem while here, look for a product called Sinofresh. It's an over-the-counter non-medicated nose spray that is sold at local drug stores (CVS/Walgreens/Osco in the allergy/sinus section). It's not a massively marketed product, so I don't think it's available in all markets. It's a little expensive ($15), but I think it works - it's an antiseptic spray for the nose that cleans out dust/mold/etc. Check the label before using (even though it's non-medicated). Personally, I've never had a problem with getting non-smoking in downtown Chicago when booking via Hotwire or Priceline (and in some cases, it has been what's booked with the hotel by the service). That's not to say that it is 100% guaranteed, but there seems to be more non-smoking rooms than smoking rooms in downtown Chicago. Where I've had a problem with it is booking rooms for friends in Wisconsin via Hotwire or Priceline, where they have gotten stuck w/smoking a couple of times. When booking on PL or Hotwire, bed requests are up to the hotel and depend on the traffic of the day, too. Nothing is guaranteed, but you are not going on what appears to be a particularly busy day, given rates. The only reason I don't recommend the Palmer House is that, if you're going to be out later in the evening, the loop area can be very quiet. Not unsafe quiet necessarily, but it's largely a business district and when everyone goes home, it definitely empties out. The area North of the river remains more lively later into the night. Otherwise, it would work if you took a taxi back at night. Water Tower would be maybe a 20-25 minute walk. I definitely agree with you on the Sheraton. I still like the Whitehall EasyClickTravel idea, but Other possibilities I'm seeing: Drake - massive older landmark hotel on the North end of the Michigan Ave. shopping area, close to Water Tower. Some mixed reviews, but a definite landmark building with a lot of history. $160 on Expedia. Hotel Indigo - I recommend this newer boutique hotel a lot; it's a renovated hotel in the Gold Coast area (about a 5-7-minute walk to Water Tower) Warm color palette/decor (fits as a "romantic" hotel for couples), and around the corner from the Division/State tavern/pub area. A lot of restaurants nearby and a subway station a few blocks away. Gets good reviews. Not a 4*, but a strong 3/3 1/2* $169. Fairmont - This would be a nice 4* for $149 on Expedia. It's South of the river, right by Millennium Park. Being on Michigan Ave and close enough to the river, this wouldn't be quite as quiet as the area by the Palmer. Embassy Suites Lakefront - Not the best choice for a couple (mainly a family hotel and a lot of kids running around) but great location across from where the Sheraton is + free breakfast. $179+ free room upgrade (doesn't specify details) on Hotels.com Hotel Monaco - This is a funky (in terms of style) 4* along the river that has some fun amenities, such as the ability to have a goldfish for your stay. Wine reception at night. $175 on Expedia. Westin River North - The rooms don't have the same sleek, Japanese style that the lobby does (this used to be the Japanese-owned Hotel Nikko), but they do boast the Westin Heavenly Amenities (Bed/Shower/etc) and I feel this is a nicer property than the Michigan Ave. Westin. $180 on Expedia. Across from the House of Blues.