One of the many perks of being a Hilton Honors Aspire card holder is the free weekend night award. The award is given annually on your card-opening anniversary and must be used within a year of receipt. I recently started thinking about how and when to use my Hilton free night award.

I had until August 2019 to use the award, but my schedule has been jam packed with travel. So far this year, I had already gone to California in January and China in February/March. While I have an upcoming work trip in May and a two week trip to Israel in June, both are already booked. So there was no opportunity to use the award on any of those trips.

So instead, Annie and I decided to look into using the free weekend night on a stay-cation in Chicago. After a quick search for the last Saturday in April, I found two great options where we could get a great location and a great value.

The criteria for the search was simple:

Murray is ready for a luxury hotel stay!

Location: something in or near the River North neighborhood where there’s great dining and shopping options
Dog-friendly: we thought it would be fun to take our golden doodle, Murray, with us and wanted a hotel that would allow him
Value: the free weekend night award is a perk I get from a credit card with a hefty annual fee, so the more expensive the room, the better

The options came down to the Conrad and the Waldorf Astoria. Both are in great locations and are dog friendly. So the tie-breaker was value.

The cheapest rate for that Saturday night at the Waldorf Astoria was a prepaid $337. With taxes, the total would come to $395! And flexible rates were in the $400s.