I have a bunch of Hilton points burning a hole in my pocket. Trying to decide between the two for a four night vacation in late spring.
The locations are similar (slight nod to Conrad). The Drake is older, I assume rooms have been remodeled, but the Conrad is probably the better bet.
Fairly easy decision for the Conrad. The Drake has some nice rooms, but the average room there can be old and small.
I live in Chicago, and I’ve been in both, but only stayed at the Conrad. The only reason I stayed at the Conrad was because I got a special offer.
The Drake is old school. Very old school. And it’s old. I don’t know what the rooms are like, but I’ve been to several events there, and they were all VERY nice, well done, fancy affairs. They cater to fancy and elegant. I imagine if you like the old school charm, you’ll enjoy the Drake. The Drake would be an experience. But my experience with old hotels is you can get a magnificent room, or you can get a really small, dumpy room - sometimes luck of the draw - and if you have status, it may help, or if you are using points, it may not.
The Conrad was nice, new, modern, clean. Sort of a high-rise hotel. If you get the right room, you can get some great views. It was a really nice hotel. If you were traveling to Chicago and had the money, it’s a really nice hotel. But it’s not Peninsula nice. There are some other hotels in Chicago that are similar, but cater to more wealth. This is close to as nice, but without the catering to money.
The two hotels are not too far apart from one another. The Conrad is less than a block off the middle of Michigan Ave. The Drake is further up the street. Location should not be an issue unless you are taking the “L” and the Conrad is closer to one of the Red line stops.
Thanks for the tips!
Between the two is an avenue which used to be so chic and glamorous.
Conrad. The Drake is nice but old. I like the Conrad’s location better. It as been years but my last stay at The Drake they refused to honor a promotion. We went back and forth but it wasn’t much money so I just gave up. But their attitude was bad enough that I swore the place off.
I would stay at the Waldorf if you have enough points.
I would not stay at Drake. Like other have said it needs a complete remodel.
Keep an eye on the Covid restrictions. Right now you need a negative test to come to Chicago and things are still very tight in terms of restaurants and other public places. Our numbers look pretty good but no one can predict what it will be like in spring.
George