Chicago Hotel Help!
 

My husband and I are thinking about spending the weekend in Chicago for Valentine's Day. He has a lot of Hilton points from all of the traveling that he does for work so we can stay at a Hilton for free. Our options are the Drake and the Hilton Chicago. Does anyone have any advice on which of the two we should stay at? Any help would be appreciated!

Thanks.

I've stayed at both, and personally would choose the Drake, though it really depends on what you want out of your weekend.

The Hilton Chicago is GIGANTIC (1500 rooms), and is located further south along Michigan Avenue, closer to the museums (esp. the Art Institute)and Grant Park. The Drake is smaller (only 500 rooms) and located near the Water Tower and closer to shopping and dining. Both hotels have tried their best to modernize their rooms, though I'd say the Drake did a slightly better job. Both have that old-time appeal of marble lobbies with giant crystal chandeliers, and the rooms offer spectacular views of Lake Michigan.

The two are only about 2 miles apart on Michigan Avenue, but as the above poster says, The Drake is closer to more activities and restaurants.

The Chicago Hilton was at one time, the world's largest hotel and was owned by the family of Supreme Court Justice John Paul Stevens. It was known as the Stevens Hotel and still bears "S" monograms in some places.

We stayed at the Conrad on Hilton points. It is attached to a mall and was a great located. Nice rooms too. I love Chicago and can't wait to go back.

Can you use your Hilton Honors points at the Homewood Suites? We have stayed there in Chicago and love this hotel. It is in a great location for getting out and walking and shopping. They also have breakfast and lite supper included. It is very nice having a suite to have a little more room and we had a great view of the city.
We are saving our Hilton Honors points to go back this fall.

By all means choose the Drake. It has lots of "old Chicago" charm while still being luxurious. Fabulous location. I admittedly have bad memories of that Hilton because I have attended huge conventions there and had to stand in line for 20 mins trying to get on the elevator.

This is all really helpful, thanks so much for the feedback. I didn't know about the other two hotels that you can use hilton points at. They both seem like great options, so thanks again.

On a side note, has anyone heard of anything good going on in the city for Valentine's Day. I was really hoping we would be able to see Wicked, but the schedule will be over by then.

another vote for the Drake. Old world Chicago charm. Hilton seems to have done an ok job at renovating and keeping the feel. I believe they still serve "high tea" in the lobby.

The Chicago Hilton while ok has always felt like a convention hotel to me. I've stayed at both.

To me the Drake seems better placed for shopping and restaurants.