Tomorrow, thanks to a really good sister, I will be spending one night in a fancy hotel in Chicago with my husband and without my children! In preparation I got to use a lot of the online travel planning tools and I thought I’d share what I learned.

Expedia.com
This site lets you do fairly elaborate searches, where you can pick area, class (or stars), dates, and more. They seem to offer good travel advisories, such as letting you know if the staff in a hotel are on strike and picketing. They seemed to track hotels in smaller cities too.

Hotels.com
This is a great site for getting an overview of the hotels in a given area – if that area is a fairly large city. They appear as if they will track hotels in any area – but I tried a few places and they came up with nothing. I did like their last minute deals section.

Priceline.com
Everyone else seems to have used this site – you select some criteria and then post a dollar amount you are willing to pay for a hotel that meets your criteria. The scary thing is you say yes to a type of hotel – not a specific hotel. But it seems like a great place to make a deal.

What I learned about all of the sites is that the closer to your visit, the better the deal. So, I checked back periodically to get a price that would let me spend more money on the great Chicago restaurants. In the end I got a 4 star hotel room off North Michigan Avenue for $100 from Priceline.