Hi! First-time poster, instant devotee! Great board - thanks for all of those who help us cross-eyed bidders. My circumstances are a little strange - would you like a challenge? I'm an experienced DIY traveler, but I have used HOTWIRE and PRICELINE only a few times. Would love your input for this odd circumstance. Going to Chicago for one night, July 10. Our budget is $150 per night before taxes, though of course we'd love to get something under $100. The group is 5 adults (incl. 2 couples) and 4 kids (ages 5-16). Some of us will be doing an all-night bike ride, an annual event in Chicago, so we won't really be sleeping, which means our needs are flexible. We prefer two rooms in a suite hotel, like Embassy Suites, with either king or double beds and a pull-out. We love the Hilton Suites by the John Hancock Tower (NMA-Gold Coast area), but they don't have availability. We are also open to three standard rooms at $100 or so each. And in a pinch, we could get by with 2 standard rooms with 2 beds each, if we take a chance on bidding. We really want a pool and a hot tub. We prefer Mag Mile-Streeterville or NMA-Gold Coast. Third choice is Museum Campus-McCormick Place. Regarding location, owe bike from Millennium Park to the hotel after the ride, around 5 or 6 a.m. There's low traffic that hour, so most streets are bikeable. We just need a safe area, and obviously can't get on a highway. I'm not as familiar with the area south of the park as I am north and west, so I'm a little hesitant about risking a hotel south of the park. We could easily ride as far north as the Gold Coast. My options on HOTWIRE include only 1 hotel with a pool - 4* in Museum Campus-McC Place, $79, Trip Advisor rating 4/5. Seems to be the Hilton, which matches the TA rating. Your list only includes two 4* hotels in this area, and the other is Hyatt McCormick Place, which has a 3.5/5 rating on Trip Advisor. Do you think it's the Hilton? However, according to your brilliant Calendar of Wins, several people scored the Embassy Suites Lakefront on and around July 10 for under $90. It's the most-frequently "won" hotel in that time period. I don't know when that hotel was "won" - I suppose it could have been weeks ago. This hotel would be ideal. The hotel reports no availability (I realize one of the sites could be holding rooms). I'm tempted to bid on Priceline for $90, 3.5* or 4* hotel, with the hope of getting the Embassy Suites Lakefront. I realize this is a big risk, but I'm wondering how big. What's your take? Thanks a bunch! Lucky7