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.

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

The first thing to note is the location. It’s at the top of the “Magnificent Mile,” which runs down Michigan Avenue from Oak Street down to the river. It’s a solid 10-minute walk from the nearest subway stop (the Red line @ Chicago Ave), but easy to catch a bus on Michigan Avenue. And it’s super touristy.

Looking back, I wish I’d stayed in The Loop instead so I could be closer to Red and Blue line trains because I have a couple of friends in Logan Square.

But upon walking in, I could feel the “Old Chicago” vibe peeps on TripAdvisor talk about so much.

There was no line at the desks, and they’d already prepared an envelope stuffed with coupons, a welcome letter, and a premium wifi code, for my stay.

My Diamond status was acknowledged, and they gave me an upgrade to the Executive (10th/top) floor.

But, a huge reason I picked this hotel was because of the Executive lounge. I’ve done well in the past with breakfast, drinks, and canapes at other Hiltons and was really looking forward to it. But it was closed for renovation until – get this – the following week. Arggh!

In lieu of losing that, they had these coupons for a free pastry, juice, and coffee at the Lavazza. And a free appetizer at Coq d’Or each evening. I would’ve preferred the Executive lounge. But I took the coupons, which were a nice gesture.

I had a feeling these coupons would be kind of a PITA to redeem, though – more on that later.

Though the lounge situation was a letdown, the rest of the check-in was quick. And I always love getting an upgrade!

The room at the Drake Hotel Chicago

The door opened into a small entry room. The bathroom was to the left. And the main room was to the right.

I promptly hung up all my shirts. 🙂

I could see Michigan Avenue from one wall of windows. And a view of Walton Street with Lake Michigan in the distance from the others.

I thought the room and decor was awesome. Very spacious and open. I showed the pics to one of my friends and she said it “looks like Gramma’s house.” Lolerz.

I loved the window treatments, the dark carpet, and the many pieces of art on nearly every wall. The room was bright during the day, but there were 5 lamps around the room to keep it lit in the evenings.

Though the hotel is pretty old, the bathroom was very slick and modern – but extremely small. I had trouble fitting the contents of my little dopp kit on the narrow perimeter of the sink.

In fact, the toiletries provided were stowed on a shelf under the sink instead of on top.

The room was clean and the big king bed was extremely comfy.

I had some trouble getting the room temperature comfortable as the weather fluctuated rapidly during my 5 days there. By the time I finally figured out the perfect temperature (71), it was time to leave.

I don’t know if it was my location at the end of the hall or what, but the wifi in my room was pretty weak and slow. It worked OK on my computer, but my phone was better off with AT&T’s LTE network than the hotel wifi, so I stopped trying.

I was supposed to have “premium” (supposedly faster) internet, but the signal was so weak, I couldn’t test that.

Old buildings like to talk, and this one was no exception. I kept hearing little creaks and whimpers from the heating system and from… really, the building itself. It wasn’t annoying, just worth a mention. I kinda liked it. I wanted to see a ghost. 🙂

Overall, I was pleased with the room except for the wifi. Clean, quiet, comfy bed… the basics were there. But I did have to work in my room for a couple of days, and it was challenging to wait on the internet speeds.

Breakfast or, The Battle of the Coupons

I knew those little coupons were a half-baked concept. When I saw them I thought, oh here we go.

A few of the employees didn’t know what to do with them, what they were for, or what I could actually get with them.

For breakfast the first day, I tried to order a tomato croissant, an OJ, and a coffee.

Uh-uh, the lady said. “You can’t get that!”

“Oh… what can I get?”

“Anything in the pastry case!”

“But… the tomato croissant is in the pastry case.”

“You can’t get that but you can get anything else in the pastry case!”

I was dumbfounded. “OK, so can you show me what I can get? Because I’m confused now.”

She pointed at the pastry case again, and I was getting a little annoyed. I said, “Just pick out anything that’s not too sweet. I don’t really care what it is. Just pick one.”

“You can have the almond croissant!”

I kind of rolled my eyes and said, “Sure. That’s great.”

And grabbed it all and went back to my room.

The next day, I presented my little coupon again.

There was a different lady so I asked again what I could get with it. Again I heard, “Anything in the pastry case!”

“Can I get the tomato croissant?”

“Sure!” she said and put it in a bag. Weird, I thought.

The next day, there was yet another lady in the Lavazza coffee shop.

I tried, again, to get the tomato croissant. She paused. “I’m not sure!”

Before she could say anything else, I yelped out, “Bagel?!”

So I got the bagel that day.

Again, I would’ve preferred the Executive lounge for breakfast. Or a buffet. But the buffet was $14 (half off) with the coupon. So I said no way to that.

The same thing happened at Coq d’Or restaurant, where I could get an “evening refreshment” from 4 to 8pm.

The service was painfully slow. One evening, I had to ask 3 times for service after sitting for about 15 minutes without a greeting or menu. But I was determined to use my coupon.

The server told me I could get any of the appetizers or a flatbread (all around $15). So I asked for the chili. One night, no problem! Another night… you can’t get that. “OK, well what can I get?” *exhale* It was kind of an ordeal every time. Kind of amusing, kind of annoying.

But, they also had a decent $6 happy hour in the evenings, so I got a snack and a beer for $6 – not bad. But again, not the Executive lounge (can you tell I’m real butt-hurt about that?).

In short, this coupon system ended up being trouble for everyone involved. But the free food was worth it, I guess.

Bottom line

I mostly liked staying at The Drake hotel in Chicago. I got a 5-night stay in a room valued at ~$1,400 for 200,000 Hilton points, which is a great deal. I am always flush with Hilton points, so don’t mind burning them. Hilton throws points and me left and right – which is why I love being a Diamond member.

This hotel is certainly a Chicago landmark – with a ritzy address to match. But, I wouldn’t stay here again.

I missed being near the trains and found the location a bit too touristy for what I wanted. There’s also a severe lack of restaurants in the immediate area – although there are a ton of them in other Chicago neighborhoods. I ended up taking a Lyft to get most places because of the long walk in the cold.

Maybe if the Executive lounge had been open and the wifi a bit faster, I’d have a different report. But I’d still rather have a better location than give this one a second chance. It’s fantastic if you love historic buildings, or want to be on the Mag Mile to shop. Other than that, I’d say go elsewhere – there are plenty of options in Chicago.

If you’ve stayed here, how did your visit compare? 

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