Why Chicago
Crazy piece of minutia: SSO and I have the same birthday (day and month at least, only the year is different). On my ‘big one’, SSO planned a weekend in NYC to celebrate with our sons and their partners. It was fabulous and the Peninsula Hotel was an outstanding venue for the occasion. This year was SSO’s ‘big one’. So, we reached out to the boys suggesting several different locations to honor SSO’s Birthday including London, Paris, San Diego, NYC. Surprisingly to us, they came back with a different option, Chicago. It made sense, Chicago was a relatively easy meeting place for all of us to get to (from CO; CA, VA and MA) and easily doable for a weekend without arriving back exhausted and jetlagged. Chicago it was.
Why AMEX Fine Resorts & Hotels
My first, and only source for booking a hotel was AMEX Fine Hotels and Resorts. The benefits are fabulous when travelling for a weekend, especially when you need 4 rooms. Many hotels will oblige to pool the room upgrades and give us a larger suite which we can use to meet in before and after dinner or just hang out in together. The 2 breakfast credits/room is ample for feeding 4 big breakfast men and 3 light breakfast women. The early check-in is a huge bonus especially when you are arriving on the red eye from the west coast and need a few hours of sleep before feeling alive again. The late check-out is also a huge bonus especially when you are only in a city for the weekend and have a later flight on Sunday. These early check-ins and late checkouts facilitate getting the most out of a weekend away. In fact, I had looked at an Airbnb / VRBO house, but for those very reasons, we nixed that idea early on.
Why the Pendry
Given the Family was only going to be in Chicago for the weekend, we wanted to be centrally located and at a hotel we would all enjoy. I had narrowed the choice down among the Langham, the Waldorf Astoria and the Pendry and was watching their rates on AMEX for weeks before booking a hotel. They were fluctuating quite significantly (important to lock it in on a low especially when you are booking 4 rooms). When rates started to settle, it turned out that the delta between the Pendry and the Langham/Waldorf was quite significant ($150/night per room; x 3 nights x 4 rooms = $1800). I would be the first person to admit the Langham/Waldorf are more elegant hotels than the Pendry (more in line with the Montage, the Pendry’s more upscale sister hotel); but given the ‘use case’ (a weekend enjoying the sights of Chicago and some great meals together) and the target audience (3 young men under 30 years old and their partners), the Pendry would be just fine, in fact, what am I thinking? More than just fine. Pendry properties’ reputation and from our limited experience (see: Pendry Park City) exude understated luxury, with interiors clad in elegant neutrals, elevated dining options and impeccable service; it is just more like an 8.5/10 versus a 10/10 for the Langham (see: Langham London)