To add to milepig's itinerary, I'd also suggest strolling along Wacker Drive from Michigan to Lake, and taking the "L" for these segments (day or night): Brown Line out to Armitage, Pink Line out to Damen, and Orange Line out to Halsted. Personally, my favorite angle on the skyline is from the west-northwest, rather than from the lakefront; since the skyline extends west and north from the loop, those just northwest get to be enveloped by city lights.

Some mid-range hotels with good river views: Hotel 71, Club Quarters on Wacker (not on Adams), and the Holiday Inn at Mart Centre -- which wins the award for "ugliest building with the best view." Some high-rise hotels a bit removed from downtown have good views on clear days, like the Hyatt Regency McCormick Place or Crowne Plaza Metro.

Rooftop bars have become a fad lately, and offer some really great views -- and you don't even have to buy a drink.

Chicago has many boat tours, from seeing the river from an architectural view point to dining and seeing the city from the lake at night. Both these companies are Chicago institutions and have been around for years. Both will meet your wants. Spirit of chicago will also give you a dining experience as well. You want a lake tour to see the skyline at it's best. Most river tours will take you through the locks and enter the lake, but the lake tour will take you up and down the skyline for the best view. Seeing the skyline from the lake at night is a glorious experience.

http://www.shorelinesightseeing.com/

http://www.spiritofchicago.com/ch/in...FQ8MDQodiFOE7w

I assume you are asking about lodging? Based on many of the sugestions here take a look at where the Fairmont Hotel is (and there are plenty more in that area). This is a good location that would allow you to get to the Adler and Millennium Park and the lakefront. The loop is fairly dead after business hours so I wouldn't do that. An evening walk north on Michigan Avenue is really nice. If you have time during the day you can continue north along the lakefront (see: Oak Street beach) towards North Avenue beach. The views back south are great. Going to Adler to the south and North Ave beach to the north is fairly agressive. I think we are assuming that "wandering" means likes to walk distances.

Others can chime in, but I'm thinking a round trip starting at Millennium, going to Buckingham Fountain, south and east to Adler and return would take at least a couple of hours walking at a decent pace but allowing time to take in the sights. A round trip from the Fairmont to the end of Navy Pier an hour and a half (again briefly taking in the sights, but no alotment for relaxing)?

I would Priceline a hotel in either the Millenium Park/Loop or N. Michigan Ave. areas. The areas are fairly compact and walkable between each other.

I would check prices at the Blake Hotel. Good location in the near South Loop for what you're wanting to do, and they sometimes have great rates (and sometimes don't). Avoid the Congress Hotel at all costs, and also the TravelLodge on Harrison unless you want bedbugs.