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priceline question-chicago hotels

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We are trying to get a hotel room on priceline for a Thursday through Sunday stay, September 14-17 in Chicago. It seems that in Chicago, weeknights are quite a bit more expensive than weekends at many of the hotels and I'm wondering if the Thursday is hurting our chances of getting a decent price on Priceline for a room. I've read the bidding for travel site over and over and it is one of the most confusing sites I've ever seen and I can't seem to get this question answered. I'm hoping someone here will have something intellegent to say about this.

Should we try to do 2 separate bids and maybe switch hotels? We've looked for a backup to book so we can just keep trying and hope something opens as we get closer to the date but even the 2-3 stars downtown are close to 200 a night. We've been bidding for 4 star hotels on Priceline and have gone up to $150 for the 3 nights with no luck.

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