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Hotel Review: The Drake (Hilton), Chicago

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.

the drake hotel chicago

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.

Arrival and check-in

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Lyft: Cheaper & Better Than Uber, Now With Cashless Tipping

It took me a long time to get into the whole “Uber” thing. I was always like… why not just take a taxi?

The price wasn’t that much cheaper until recently.

The few times I uber-ed, the main thing I liked was the cashless tipping. The price, all things considered, was equal to a cab (I say/write this in NYC).

Then, they slashed fares. 

uber vs lyft

Underdog extraordinaire

And, I started going to Dallas a whole lot more, without a car. I grew accustomed to firing up Uber as I walked outside and getting a ride to my condo. Again, with the cashless tipping.

I love the simplicity of the bundled fare. You just get out when you arrive, and you’re on your way. The receipt comes via email seconds after the door closes.

…But now there’s no cashless tipping

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