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Luxury Chicago Hotel for Couple

Posted on 6/10/26 at 11:28 pm
Posted by donRANDOMnumbers
Hub City
Member since Nov 2006
17533 posts
Posted on 6/10/26 at 11:28 pm
bringing my wife for her 40th birthday.

ive been to chicago a few times and love the downtown area. there are so many options to choose for stay, its overwhelming.

i narrowed down to the Langham or Trump International.

hard to find public reviews on TI though because of Trump's polarization. (ie reddit hates him)

but was hoping for some opinions here.
Posted by deltafarmer
Member since Dec 2019
981 posts
Posted on 6/11/26 at 5:08 am to
You can’t go wrong with either of those. If the Trump hotel is cheaper then I wouldn’t hesitate to stay there.
Posted by b-rab2
N. Louisiana
Member since Dec 2005
12962 posts
Posted on 6/11/26 at 6:54 am to
If you have Hilton points stay at LondonHouse Solid hotel.
Posted by Buck Dancer
New Orleans
Member since Jan 2008
4867 posts
Posted on 6/11/26 at 8:04 am to
We stayed at LondonHouse last time and it was very solid and in a good location. Across the river from Trump Hotel.
Posted by longhorn22
Nicholls St. Fan
Member since Jan 2007
43418 posts
Posted on 6/11/26 at 8:14 am to
London House hotel has a great rooftop!






We stayed at the Pendry last time in Chicago. Top notch! They also have a great rooftop.




If yall are "sporty" in a way look into the Chicago Athletic Association

have Cindys rooftop that overlooks the bean and also some cool spots inside the hotel to hangout in and get a good cocktail. One of our favorite hangout spots.


Posted by Chucktown_Badger
The banks of the Ashley River
Member since May 2013
37554 posts
Posted on 6/11/26 at 8:20 am to
quote:

i narrowed down to the Langham or Trump International.


GF used to be the director of sales there. Great spot.

The St Regis is pretty awesome as well.
This post was edited on 6/11/26 at 8:21 am
Posted by Motownsix
NOLA
Member since Oct 2022
3390 posts
Posted on 6/11/26 at 8:39 am to
For me i like to stay in certain sections of Chicago for different reasons. Each one has their supply of upscale hotels.
Recently stayed at The Drake in the Streeterville/Gold Coast hood and liked the hotel a lot.
Posted by Chucktown_Badger
The banks of the Ashley River
Member since May 2013
37554 posts
Posted on 6/11/26 at 9:35 am to
quote:

Recently stayed at The Drake


Are those rooms really small? Would be my concern given how old it is.

Also, obligatory

This post was edited on 6/11/26 at 9:37 am
Posted by yellowfin
Coastal Bar
Member since May 2006
99034 posts
Posted on 6/11/26 at 9:52 am to
Our room at the Drake was small and it was a mid tier room. It was also dated
Posted by donRANDOMnumbers
Hub City
Member since Nov 2006
17533 posts
Posted on 6/11/26 at 10:02 am to
i had London House on the list as well due to the rooftop bar!
Posted by NOLALGD
Member since May 2014
2790 posts
Posted on 6/11/26 at 11:35 am to
quote:

The St Regis is pretty awesome as well.


This here. Also think about your view, some hotels are better for skyline and river views, others have more rooms with great lake views.
Posted by Donkus
Shreveport
Member since Feb 2013
1650 posts
Posted on 6/11/26 at 12:21 pm to
Sofitel Magnificent Mile was great with several high end restaurants within walking distance. Also having a grocery on the same block came in clutch a couple of times.
Posted by hoopsgalore
Chicago
Member since Nov 2013
9158 posts
Posted on 6/11/26 at 1:43 pm to
quote:

i narrowed down to the Langham or Trump International.



Stay at The Langham.
This post was edited on 6/11/26 at 1:44 pm
Posted by OhioLSUfan
Columbus, OH
Member since Oct 2007
2061 posts
Posted on 6/21/26 at 4:34 pm to
The Palmer House Hilton is my vote
Posted by Chucktown_Badger
The banks of the Ashley River
Member since May 2013
37554 posts
Posted on 6/22/26 at 12:53 pm to
quote:

The Palmer House Hilton


The lobby is beautiful but that's about where the "luxury" goes there. I did not like it at all. Rooms are small, dated, a bit dingy, there was no coffee in the rooms...I could go on. Not in the same universe as some of the other hotels being considered.
Posted by EKinGB
Member since Oct 2025
6 posts
Posted on 6/25/26 at 10:04 pm to
The Fleid Museum is underrated for kids. The Shedd Aqurium is awesome.Linc Parc Zoo is ok.
Posted by HoustonGumbeauxGuy
Member since Jul 2011
33739 posts
Posted on 6/27/26 at 7:38 pm to
Honest question.

What’s the point? If you’re visiting an amazing city like Chicago the last place you wanna be is in your hotel room.

Same concept applies to Las Vegas
Posted by donRANDOMnumbers
Hub City
Member since Nov 2006
17533 posts
Posted on 6/27/26 at 10:31 pm to
its all about the wife being impressed, and bang for your buck.
Posted by LemmyLives
Texas
Member since Mar 2019
17562 posts
Posted on 6/27/26 at 10:54 pm to
quote:

If you’re visiting an amazing city like Chicago the last place you wanna be is in your hotel room.


Geez. You should already know by now that opening the door to the room, seeing the view from the room, sets the wife's expectation on whether you've F*ed up or not for her birthday.

OP, tell the hotel what the occasion is, and the $4 worth of cheesecake they put in your room will make your wife think you cared that much. You spent nine seconds worth of effort to tell the hotel you wanted something special in the booking, and you benefit. Oh wow, what a surprise!
Posted by donRANDOMnumbers
Hub City
Member since Nov 2006
17533 posts
Posted on 6/30/26 at 2:27 pm to
QUICK UPDATE ON OUR TRIP

We ended up not making a decision until last minute but accommodations worked out just as well.

Stayed at Trump International in a Deluxe Suite River View for 3 nights.
The room was very nice, and very big. The view was excellent.
Wife was interested in staying in the Langham. But when i brought that up on the trip she cited how amazing our view was at Trump, so it was a win.
It was also priced better, about $800 less than Langham overall. (The room wasn't less per night technically, Trump Intl had a deal where the 3rd night was free. So two nights in that suite were less than the regular King Room at Langham for the same duration)

I would stay there again, but would likely try another spot out since there are so many options to explore.

Two Dinners:

1. Gene and Georgetti - we wanted to go somewhere that felt local. I am glad we went, but would likely not go back. The old fashioned was excellent. The food was good, but not great.

2. Gibsons Italia - this restaurant is incredible. Should be at the top of anyone's list.


Two Lunches:

1. Sushi San - great sushi spot. wife didn't want to drop straight into a pizza place off the bat. it was good, but would likely try a different place since there are so many options.

2. Lou Malnati's - great pizza spot. Would recommend going for the nostalgia. I would try other spots out for same reason as others.
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