This past week, I ventured up to Chicago to see Hamilton and hang out with some old college buddies.
I booked 5 nights at The Drake hotel Chicago, located on the Magnificent Mile/Michigan Avenue, with Hilton points. The 5th night was free on this award booking, so I paid 200,000 Hilton points (50,000 X 4) for the entire stay.
My eventual room would’ve cost $1,400+ out of pocket
Because I’m Diamond with Hilton, I got an upgrade to a King Bed on the Executive Floor. Similar room rates to when I stayed say this would’ve been ~$1,404 in cash. But I didn’t have to pay taxes on the award booking, which are over 17% per night (!!!).
That means my Hilton points were worth .07 cents each – and more when you count the free breakfast and free food in the evenings. That’s a good rate for Hilton points!
I took a Lyft from Midway after flying on Southwest from Dallas-Love Field. Traffic was backed up, but I made it to The Drake in about 30 minutes.
