My wife and I are traveling to Chicago 8/1 - 8/4. We have a cancellable room now ($25 cxl chg). My primary question is the old "bird in the hand" scenario. I know the "what if" scenario is impossible to answer, but I'm looking for a best guess on pricing at this point. Ultimately, do I wait a little longer and continue to bid Priceline and watch Hotwire, or do I pull the trigger now. See details on current pricing below. That weekend is unfortunately the weekend of Lollapalooza in Grant Park in Chicago. Our plan is to focus on 4* plus in the North Mich. Avenue area, thinking the young folks will look to stay in the Loop or close to Grant Park in more affordable (lower * levels). The thought is that the demand for NMA 4* plus will be less than south of the river (all other things equal). Good plan?? Here are my 3 options, as I see them. Which one is the best strategy in your opinion? (ThereUAre & AaronJB) 1) Buy the following, which is now available on Hotwire (2 people; 8/1 - 8/4) for $219/night - 4.5 * Magnificent Mile - Streeterville - Fitness, Pool, Rest., Bus. Center, High Spd Internet; Customer Favorite; 4/5 rating on TripAdvisor. I believe this is a match for InterContinental or Hilton Conrad. Rates per the web are $284 InterCont.& $277 for Conrad. If the TripAdvisor rating is an indicator, it's Conrad, not InterContinental. OR 2) Split the stay to save a few more dollars. A) Buy on Hotwire (2 people; 8/2 - 8/4) for $183/night - 4.5* (same as above) Magnificent Mile - Streeterville - Fitness, Pool, Rest., Bus. Center, High Spd Internet; Customer Favorite; 4/5 rating on TripAdvisor; and :) Buy on Hotwire (2 people; 8/1 - 8/2) for $233/night - 4* North Mich. Avenue - Water Tower- Gold Coast - Boutique, Fitness, Rest., Bus. Center, High Spd Internet; 4/5 rating on TripAdvisor. I believe this is a match for The Raffaello Hotel. (This B option would cost the same $233 if booked for all 3 nights; Hotel A drops from $219 to $183 if I drop of the first night). OR 3) Wait and continue to bid PriceLine and monitor Hotwire offers. I have been bidding Priceline permutations for NMA with 3 free rebid zones up to $140 (+$10 bonus; total of $150) for the last few weeks. Last night was the last time I bid. My thought is that the availability and pricing could change soon as some hotels wait until the last 2 weeks before a date to offer to Hotwire/PL or to drop prices. Your thoughts? Thanks for your help!