Got this hotel on the 11th bid. Began targeting a 4-star in the Millennium Park zone. Bid $60, rejected. Added Midway Airport zone, bid $65, rejected. Added North Michigan Avenue zone, bid $70, rejected. Added Greater Chicago zone, bid $75, rejected. Had my traveling partner try, began bidding again on the same four targets -- $80, $85, $90, and $95 for 4-star hotels; all bids rejected. Then I tried again and bid $85 for 3-star hotel in Millennium Park zone, rejected. Added North Michigan Avenue, bid $90, rejected. Then our last bid was to add Greater Chicago zone and up bid $95; that's when we got the Marriott Medical District. Not happy ending up with a room outside the Loop, in a hotel that is only four stories tall, but this area is only a few subway stops away from the city center so hopefully it will be okay. Considering this hotel lists for $199/night on marriott.com, it makes our $95 winning bid (which I consider a high amount to pay on Priceline for a 3-star hotel) look pretty good. Is it always this tough to score a good deal on a weekend hotel in Chicago?