I spent this past weekend in Chicago with one of my sons. It was my first time in the city, and we did some of the typical sightseeing stuff, including the Shedd Aquarium, the Adler Planetarium, and Navy Pier. Another highlight was the water taxi along the river through downtown. Hindsight shows me this was far too little time in Chi-Town.

We spent our first night near the airport after a late flight in, but the next two were downtown. I split our two nights between the Thompson Hotel Chicago and the Talbott Hotel. Both are recent additions to the World of Hyatt loyalty program. The Thompson is from the chain of the same name while the Talbott is part of the Joie de Vivre chain (SEE: Reminder: Earn 8,000 Points and a Free Night Trying New Hyatt Brands). I used a Hyatt free night certificate at each.

Value Then, Versus Value Now

When I booked the properties, rooms at the Thompson were going for $206 before taxes. Not a bad use of the free night certificate, but nothing earth-shattering. The value at the Talbott was similar. Queen rooms were priced at $165 per night. Some of you might be thinking its crazy to burn a free night for that, but hey, I like saving cash.

But I do have a limit where I’ll hang onto points or a free night certificate. Unfortunately, I happened to check the Hyatt app just after we’d checked into the Talbott to find that rates for a queen room had dropped to a mere $90 per night! Tack on some taxes, and you’re looking at barely over $100 for a stay at a solidly 4-star hotel near the Magnificent Mile.

This was a major bummer, as it was too late to walk back my use of the Hyatt free night certificate. The property is in award category 3, charging 12,000 points for a free night. I try to always get 1.5 cents per Hyatt point, so no matter how you slice it, cash is the better deal in this cash. I wish I would have taken a second look at the hotel rates a couple days prior!

Free Is Still Free

All I have to fall back on is the fact that our weekend nights in Chicago were completely free. I definitely prefer a free stay over paying cash. But it’s also a bummer to “waste” a Hyatt free night certificate when I could have forked over a single Benjamin.

Or maybe spending a free night this way isn’t really a “waste” as all and I should just be thankful my stay was free. It all depends on perspective. I’m still sitting on a couple more certificates, so maybe it is best that I burnt it.

What do you think?  Was this a reasonable use of a free night? Or do you see it as a waste?