Happy Labor Day! Our Stay @ The Waldorf Astoria Chicago (Again)

Just got done with an amazing last minute forced redemption! When my wife signed up for the Hilton Honors Surpass card way back in 10 Sep 2017 she received the bonus of a free weekend night on 10 Sept 2018. However I went an entire year without using it until my quarterly audit of free nights revealed this old email:

I had only a 2 week window to redeem this free weekend night, naturally I went with the most expensive property I could find for a staycation:

Eight hundred and sixty five dollars! This seems insane by even NYC standards! I booked the lowest level room with the cert, but got this email from the concierge days before our check in:

Ms. (Dr. Derp)

Thank you for choosing the Waldorf Astoria Chicago for your upcoming getaway!

As a Hilton honors gold member, part of your benefits are a complimentary one level upgrade based upon availability upon your time of arrival.  Should an upgrade be available when you arrive, we will be happy extend this benefit to you!  If you wanted to secure a multilevel upgrade prior to your arrival, I would be happy to assist.

Upon reviewing your reservation, I am able to offer a upgrade of four tiers—putting you in the Deluxe One-Bedroom Suite
 for a difference of $140 per night.

The Deluxe One-Bedroom Suite, at a spacious 760 ft2  features a living room with Queen sleeper sofa and a beautiful walk-out terrace, private King bedroom, fireplace, corner views, additional powder room.  Please contact me if you would like to secure this enhancement. 

Furthermore, as your personal concierge, I am also happy to assist you with securing dining reservations, spa appointments, airport transportation, in-room amenities, and any additional preferences you might have.

May I note your estimated time of arrival? I look forward to speaking with you.

Warmest Regards,

Charlie Schumacher | Personal Concierge

Telephone: (312) 646-1300

Note that my wife is not DIamond since she has not opened a Hilton Honors Aspire card (yet) since she is just coming off her 5/24 fast. However she had gold because of her AmEx Platinum! Like a sucker I went for the $140 upgrade on top of mentioning that it was my wife’s promotion to O-5. I also pressed on the concierge about any amenities offered for a guest with diamond status and he had this to say:

Mr. & Mrs. (Derp),

Congratulations on your promotion!  May I send a complimentary bottle of Champagne to the room to help celebrate?

I’d be more than happy to secure your reservation for an upgrade, into our Deluxe One-Bedroom Suite.

Unfortunately we are only able to attach one profile to a reservation.  But the great news is on property both Gold and Diamond member receive the same benefits so no need to change the profile!

Will you by chance need restaurant recommendations?

No love for Diamond members, but upon check in we did get a nice deluxe one bedroom suite, and a bottle of $60 Chandon from Napa Valley (notably NOT Champagne, but I get it):

The dining in menu price for a bottle would be $60:

Oh well, at least a nice card came with the whole bottle:

The room was nice, but it had a balcony that looked over to an alley, but you could catch all the hijinx occuring on rush street below:

Not bad for $140 I guess, but I would be pretty pissed if I paid $860 for suite #1104! The tub was nice and deep and I had an entirely separate powder room to befoul! The fireplace and couch in the sitting area was a nice touch:

I wish it was a resort, just to be able to raid the minibar for the $250 in credits:

The Hilton gold status also came with free WiFi as well as a $30 credit for food:

We ate at Margeaux Brasserie for dinner, and they applied the $30 credit to that meal on checkout. It was a much better option since they gave little coconut muffins as a departing treat. I enjoyed it with my butler delivered coffee wake up call the next morning:

The butler was very nice and fetched more Salvatore Ferragamo toiletries and water bottles:

One unexpected amenity was a free book at turndown service:

I am not sure if I would have gone for the upgrade again for $140. Honestly I got kinda lost in the middle of the night in the one bedroom suite! It would be perfect for travel with large families.

In about a year I should have 6 of these weekend nights coming to me annually from my upgrade of lower tier Hilton Honor Cards. It might be better to book two simultaneous adjoining rooms to accommodate groups of people, rather than one giant room! What a good problem to have I guess. Do you prefer suites or adjoining rooms?


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