How I book ritzy hotels cheaply

Joe and I stayed at the Intercontinental on Michigan Avenue (in Chicago) last week, and we paid very little to do so. Some friends have been asking about how I get my killer travel deals, so I thought I'd share.

I first check sidestep.com, which finds deals for me that I couldn't easily find on my own. I like Starwood hotels (Sheraton, Westin, and W) best, and if I book directly, I get points toward free travel. Sidestep also gives me a ballpark figure for hotels in the area, on my dates. Be sure to sort by price, or star rating, not by featured hotels or whatever odd thing the default is.

Next, I check hotwire.com and I only look at 4-star hotels or higher. I'm a stickler about this - I learned the hard way. The catch is you don't find out the name of the hotel until you pay. So then I use betterbidding.com to check out the list of Hotwire hotels. They list hotels by Hotwire's criteria (location and amenity), so you can make a very good guess as to which property you're actually getting for a certain price, before you pay. Once or twice, I did get a surprise, when Hotwire added a new property, or changed the star rating or amenities for a hotel. That is a risk, but it's kinda fun, like a grab bag!

Then, once I have a good idea which hotel or hotels I'll end up with, I check those out on tripadvisor.com (awesome site if you don't already use it) to see what the hotel is like, what's nearby, how much parking is (sometimes up to $50/night in Chicago, and not included in the cost of the room through Hotwire), if there's a "resort fee" added on, etc. Often, you can find, in their reviews, what people paid for that hotel on Hotwire or Priceline, which is nice.

On Tripadvisor, keep in mind there will always be some disgruntled people. If the majority of reviewers say a hotel was dirty, I believe them, but if one person says they didn't like it because bottled water was $4, or because the valet was rude to them, I may discount their review. You just can't please all of the people all of the time.

Only then do I book a hotel. I average $80-150 for very nice hotels everywhere, except NYC which is pricier, and you can probably do better off Hotwire.

It's quite the process sometimes, so you have to be really cheap or find surfing relaxing. But I probably save thousands of dollars a year this way, which means I can eat well when I get to my destination, or travel more.