Whiskey Sky

Whisky Sky is a nice, small lounge in the W hotel with a certain amount of trendy. This is a good place to take out-​of-​towners with its nice cityscape view after dark. The drink (for me, wine) selection is nothing special. The crowd is sometimes interesting (my last time there I talked with a woman who claimed to have hopped on a plane from NYC just for the W’s spa). Bearing in mind that I am not a big nightcrawler and am not super picky about my night spots, I would recommend this place.

I came here for New Year’s Eve and it was perfect. Not too crowded, lots of drinks and overall fun environment.

This bar was a real disappointment. Tiny, freezing (waitresses warming their hands on the candles) and empty on a Saturday night. The views of the lake ?? Couldn’t see any great views I read in other reviews. Not worth the visit.

Whiskey Sky. It sounds like either a title for an album, or very cool stripper name. It is neither, but it is the name of the lounge/​bar located on the top floor of The W Hotel. This place is very small, but I was forewarned so I wasn’t in complete shock. There is seating alongside the windows, and a few small tables, and the small bar area. We went here for to have a few drinks for my friends birthday, also because another friend of mine was spinning there that night. No, not spinning like spin class, but providing the auditory stimulation for the evening.
The drinks are on the pricey side, but that is to be expected at a place downtown, right across Lake Michigan. The music was obviously exceptional, and the company was as well. This place is very intimate, and don’t expect to have a dance battle in here. This is exactly what it needs to be. A lounge where you can just chop it up and zone out. Please google the previous sentence, if you do not understand what I just said.
This is a great spot to watch the Fireworks from Navy Pier on Wednesdays and Saturdays during the summer months. Also if you don’t feel like going to some obnoxious club/​bar downtown, this place is a good alternative. I enjoyed my time here, and would definitely come back.

First of all, this is the W. You’re going to pay for drinks, get over it. This particular W hotel does not have a sky patio bar, so this bar is on the 33^rd floor but totally enclosed. The place is tiny and so is the bartender… well, not all parts of her are tiny, but ummm yeah. We were up here at 10pm on a Tuesday and fireworks went off at Navy Pier, awesome view. Bathrooms are a bit weird, since there isn’t a main door, only a see-​through curtain. Make sure you button up prior to going to the sink because everyone can see you as they walk by.

It makes me sad to see everyone not having a great time here!
My friend and I came here on a Sunday night while staying at the W. I was very impressed with the views of the city from the place! The bar was empty and Pricilla was our Mixologist. What an absolute delight she was! She MADE this bar! We sat there for at least an hour and a half talking about shit and when she asked us what we wanted, we didn’t really know what to get! She asked if we wanted to «try something new» in which she took what flavors and alcohols we like and made AMAZING cocktails!
I would NOT be able to give less than 5 stars for the amazing service and drinks that she gave us! I will definitely come back to visit her!

Great view of the lake and Navy Pier, but over priced drinks. The decoration is outdated (90’s). It’s time to revamp the place.

I stayed at this hotel which was very nice considering its location and view but I must say that the bar did not have that appeal to me which I encountered when entering the hotel’s lobby. The bar was mediocre at best and its crowd was okay as well. There was music playing by a DJ and the drinks were delicious, lights dimmed and the views were awesome. As a bar, it’s alright by me but as a night time party in the windy city, this was not the spot. Look to dance elsewhere.

This place has totally beastly views of Navy Pier. But, once you get past that, it’s small and hosts an awkward crowd. Plus, the drinks were way overpriced. A cool stop once, but I probably won’t be back.
The bathrooms were pretty cool, though.

Good news, everyone: I found the creepiest place in Chicago.
I have been to a lot (a LOT) of bars and lounges in my time, and as a frequent business traveler that includes the bars/​lounges in some of the swankier and trendier hotels. I had high aspirations for Whiskey Sky (get it? because it’s HIGH UP?) but ended up just feeling blind and not buzzed when I left.
Allow me to explain: this place is like being in someone’s tiny little living room — a tiny little living room where it’s so dark you can hardly see the bar and the carpeting looks like it hasn’t had any love in a long time. Also, the service wasn’t great and the martinis are $ 14 and not too strong — all in all, not really worth your time. There are many better bars and many better places to get a pricey cocktail. But okay yeah the view is cool so take some photos and get out.

Over price. Not worth going up the elevator even if you are on the 30^th floor.

I went to this bar last night with a friend of mine. One of my favorite bars back home is Whiskey Blue in the W hotel in New Orleans. I had also heard of other W hotel bars and lougnes so I thought I had a pretty good idea what Whiskey Sky would be like. I couldn’t have been more wrong.
The first thing that stood out was that this place is tiny. My apartment is bigger than the lounge. The only available seating is against the window and at the bar. There aren’t any tables in the middle of the bar. To be fair, if there were tables around, then there would be absolutely no room to move around. The margarita I had was expensive but at least it was strong. My friend had a strawberry mojito and she seemed to like it. The music was also very loud.
I love the W hotel brand. I’ve stayed in them before and know how trendy they can be. That being said, I was really disappointed when I left Whiskey Sky. I expected a lot better.

I’ll be honest. There is a hella lota yuck up in here on the 33^rd floor.
Between the godawful loud dance music (they are playing an actual remix of that dreadful «She’s Homeless» song from uh, 1991?!) and the people trying to be «hip,» I feel like I’m about to witness the worst Jersey Shore dance off in Chicago (to be fair, this lot is wearing Armani instead of Christian Audigier. I’ll put it to you this way, if this were summer, there would be some egregious mandal action going on).
The downstairs lounge which is a bit more civilized (but still full of decidedly greasy rich young man types avec Macbook Pros on the make) closes at midnight, so I was forced to come up here to get some work done. I should have known when some giant grey haired dude was waiting for me on the elevator at floor 32 and uttered, «are you checking in?» that I was in for it. «What are you up to tonight?» I have my laptop, asshole, what do you think?
That said, I like how dark it is in here and I like the view of the glittering skyscrapers and the bartender is nice AND I am drinking a delicious absinthe cocktail.

Went here for a private event and this place was nothing like anything a W should be like! I love their patio lounge downstairs, but Whiskey Sky is just a crampy tight unexciting bland boring little lounge bar!
And there is no lack of roof-​top places in Chicago and of course, ones with a view.
They pretend to be classier and more restricted than they really are, because really, who’s trying so hard to get in here?!

The good:
–Great view of Navy Pier
–Decent DJ the night we were there
The bad:
–My first drink was so sweet it was practically undrinkable (don’t worry, I drank all of it and got through it by complaining repeatedly). I think it was called Pure Silk and was some grapefruit number that certainly should have been more tart than sweet.
–Drink prices were steep. $ 15 for the undrinkable cocktail and then $ 17 for my glass of champagne.
The ugly:
–The group next to us all night. Cougars in ridiculous clothes (gold lame pants with zippers, another in animal print… I do have photos of the hideousness I might have to post). They made for good people watching at least.
–Crowd overall is sort of a mixed bag.

This place is about the size of a large walk-​in closet and about as equally dark as a closet with no lights in it. A group of friends and I got here a wee bit early 11ish on Saturday night and there was not much happening, only a few people at the bar and no one sitting on the couches. Bouncer did approach us to tell us that we’d have to move when the people who the table was reserved for showed up – and we were like, ok dude, this place is empty and a joke!
View is good, drink prices are steep, try the lounge/​bar downstairs (The Living Room Bar), it’s much more happening.

Since the boy and I stayed at the Dubya for our holiday gift-​exchange/​romantic getaway (getaway…like 2 miles away… but whatever), we had our pre-​dinner cocktails at the hotel bar, Whiskey Sky.
It certainly was in the sky, no doubt about that! It is a very wee bar, and it has a very posh and swanky feel. We were dressed up for dinner, and the only other people in the bar were lawyer-​looking types in suits, so I felt very elite and important. And a bit snobby. I can’t help it, I suck attitude through my pores.
We sat at the bar, instead of on one of the couches, and the bartender was a very friendly Barbie doll. I can’t remember the name of the cocktail I had, but it contained elderflower liqueur which was so delicious! So much so that it made me want to go buy a bottle of the stuff and save my money in the future! It’s a fun place to go to dress up and look at other dressed up people, and it’s worth a look if you’re staying at the W. Not sure I’d trek all the way downtown (and up the elevator) again for it, but we had a really good time and a great drink!

Whiskey Sky is a shoebox of a room with a spectacular view and not so spectacular interior. So best thing in this lounge is not the curtains, chairs, bar, bartenders, or service, but rather the windows.
Prices are a bit steep for the quality of the drinks but I guess you’re paying altitude tax. So I’m sticking to my generalization about high altitude bars/​restaurants: People are paying for the view and not for substance. Hey, take Signature Room for instance. But, to be fair, I like the Signature room much more than Whiskey Sky.
To sum it up, to walk through the swanky W hotel and then arrive 33 floors up to Whiskey Sky is a bit of a downer. Maybe Cindy Crawford should have designed this Whiskey branch, Mr. Gerber.

So the Whiskey Sky Bar was open Christmas Day at 8pm. THANK GOD!
Located on the 33^rd floor of the W Lakeshore, the view was great! Not amazing but great. Considering we were DYING for a drink at 8pm we were one of the first people there. Actually, aside from the two bartenders, there were only about 5 other people there besides us. A guy who knew the bartender, two guidos straight out of Jersey and a douchbag (because of his Anthony Robbins self-​help speak he kept laying on everyone and his pathetic rags to riches story he kept vomiting on all the patrons) and his g/​f who should have been with a much cooler guy than the douchebag.
The experience was entertaining at most. The bartenders were very sweet and helpful in helping you decide on a drink. Although pricey (it is a hotel bar) the drinks were good and because of the attentive service, well worth the price. Several drinks later and a few laughs about the douchbag later, we were having a great time!
Not sure what is it like on a normal night (not X-​mas) but it is small so it may get packed!

My friend is staying at the hotel, so a few of us had drinks at Whiskey Sky. Don’t come here unless you’ve already had a lot to drink.
It’s a small bar, and I swear, I thought a tourist in a cowboy hat was going to start doing the electric slide.