First off, thank you for all the help. Your advice led me to these two great deals. I will follow up on my second bid in separate post but I figured I would show all the pieces of the puzzle in this thread. I first tried $110 for 3.5* for both nights with no luck. On the recommendation, I bid $67 for a 4* on the Friday night only (10/9). First bid was accepted for Millennium Park, Loop & Grant Park Area and I won the Hyatt Regency Chicago (total was $84.76). Since Saturday morning was the only committed time I needed to be downtown, I toyed with going home Sat evening (3 hour train ride) or other areas/activities I could stay/do. Reading the Tripadvisor reviews, I decided to target the 4* Hyatt Regency Mccormick Place. This way we could visit the Soldier Field, Shedd Aquarium, Adler Planetarium, and the Field Museum or use 3 transit options if we decide to go downtown on Sunday. Apparently, the hotel has an hourly shuttle to downtown, a cab ride is ~$15, or the #3 bus stops near the hotel. I will be sure to report back on how this worked out. I began with a 4* bid Greater Chicago Area for $67 for Saturday night (10/10). Usually, I am bummed if my first bid is accepted when I have free re-bid zones, but I just can't believe I got it. Total was $84.76 Total for the 2 nights was $170. Thanks again, used the PRICELINE links!