Welcome to Betterbidding.
A couple of thoughts/questions:
1. PRICELINE EXPRESS only guarantees 1 bed/double occupancy, although there are listings that will offer bed choice options, and one of the bed choice options may be 2 beds. PRICELINE bidding only guarantees double occupancy; you can call the hotel after booking and ask regarding bedding, but they can say no to requests.
2. What would be your desired budget per night? Are you looking for anything particular in terms of hotel - location, style, etc? I'm quite familiar with Chicago - let me know more about what you are looking for and I'd be happy to research and offer suggestions.
3. Bidding will likely result in getting something for less than PRICELINE EXPRESS, but the issue becomes you have to be willing to accept any hotel at that star rating. With PRICELINE EXPRESS, you can make an educated guess as to what's showing, which may be worth a bit more for a greater chance at something you'll like.
Also, let me know if you have any Chicago city questions.
Please remember to return to BetterBidding and use the PRICELINE and HOTWIRE links on the board to begin your travel purchases... or thru our sister site MAPSandHOTELS.com for your regular rate purchases.