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Hotel Review: The Drake (Hilton), Chicago

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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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5 Hyatt Category 4 Hotels Where the Hyatt Card Annual Free Night Rocks

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Also see: 

I’ve had some pretty good experiences with Hyatt points, even though the way they handled their recent Hyatt Diamond promo was a disaster. #jaded

Anyway, one can have a finite number of Chase cards, but I choose to renew the Chase Hyatt card year after year.

That’s because you get a free night certificate when you renew the card each year, and it’s good at Category 1 through 4 hotels. So obviously, I try to use them at Category 4 properties to get outsized value.

Last year, I gave my free night away to Jay’s grandparents for a night at the Hyatt Regency St. Louis at The Arch (which is a Category 2), because the certificate was about to expire and it was their anniversary. Jay and I both have the Chase Hyatt card, so we gave them 2 nights at the hotel. They loved it!

hyatt category 4 hotels

New year, new options!

I just renewed the card again and paid the $75 annual fee, so I thought I’d take a spin through the Category 4 hotel list to see where I might use the annual free night in 2016.

I found at least 6 hotels where you’ll recoup the annual fee 4x over… or more. It got me thinking.

Never change

Never change

Oh, and because these are all Category 4 hotels, you can also redeem 15,000 Hyatt points for a free night. In many cases, you’ll get over 4 cents per point in value!

5 Hyatt hotels worth 4x or more than the annual fee on the Chase Hyatt card

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