Sheraton Chicago O’Hare

Last weekend was an adventure, to put it mildly. I was visiting San Jose on a $233 United fare that I had booked back in June, out Saturday and back Sunday night.

Standing in line at LGA to board, I ran into another FlyerTalker who I met on the $120 NYC-PDX fare.   While I mostly napped on my LGA-DEN leg, I ended up getting asked by my seatmate about what she could do in San Jose… for 6 hours while waiting for her flight back.   Under most normal circumstances, this question would puzzle someone; but I apparently have a “FlyerTalk vibe,” so there was no confusion about what was going on.

Saturday night, I get an email from United telling me my Monday morning CLE-LGA flight is cancelled, beginning my string of flight cancellations up until Wednesday morning.  Placed on a map, my various reroutes gave impressive coverage from a single, SJC-NYC one-way trip.

Due to automatic rebookings, it’s very likely I overlooked a few flights:

1. Morning SJC-LAX flight, connecting to UA1001, LAX-EWR.  UA1001 cancels at 8AM.
2. Rebooked at SJC to AA, AA1922 to AA746, SJC-DFW-LGA.  AA746 cancels at 9:30AM.
3. Rebooked AA1530, SJC-ORD, then connecting to AA392, ORD-LGA, on Tuesday.  While I was eating lunch, AA392 got cancelled 2 days in advance.
4. At the ORD Admirals Club, I got rebooked on AA366 for Wednesday.  I ultimately move it to AA398, the 6AM Wednesday departure, over the phone.  It got cancelled Tuesday morning.
5. I got rebooked on AA2488, ORD-BOS, ultimately  moving onto the earlier departure, AA1184, on Tuesday.

As this itinerary ultimately left me with two overnights in Chicago, I wound up staying at the aloft Chicago O’Hare (which is identical to past alofts I have visited) for 4k SPG points and then the Sheraton Chicago O’Hare on a 2.8k/$45 cash and points rate.  I booked a two room suite, which is uncommon for a basic points redemption.  Check-in required prompting to receive internet for free ($9.95/nt otherwise) as my Gold amenity.

My one and only complaint with the room itself was its proximity to the elevators.

Otherwise, I had exactly what I was promised, a two-room suite.

As I was staying on a weeknight, the hotel was charging about $210/nt for prepaid, nonrefundable rates and $249/nt for flexible rates.  In comparison, using the cost of replacement for the points, my nightly rate was approximately $123/nt and fully flexible (cancel by 6PM on the day of arrival).

Nonetheless, as ill-advised as flying into a hurricane might be, buying a walk-up fare on American Sunday morning for ~$480 would have cost about as much as my two nights in Chicago, a one-way car rental from Boston, gas, and tolls ultimately did for my return to New York.