Because It’s Fun – Y Lounge and the Redhead

Y Bar - Dirty Martini
LAX2ORD, no. 4

Stumbling up Clark Street, I asked him, “Where are we off to?”

“Why? A Lounge,” he replied.

I answered quickly, “I’m keeping track of all the places I go.”

He flashed a silly smile. “You’ll like it. It’s kind of LA. And very lounge-y.”

“So you said.” I was curious about “LA” as an adjective. I pressed gently, “Which place is it?”


Was he trying to be coy? Cute? “So I can remember it before I have too many drinks.” Nothing is cute when it comes to details of a delicious life. “You know, for the blog.”

He laughed out loud. “You’re going to blog the bar?”

It was a comedy of errors, ghost-written by a visually and aurally stimulating setting, amazing Mexican food, level 10 conversation at warp speed, and margaritas to match – all a barely lethal combination that brought out my best Spanish gibberish. Four-five-six margaritas at Frontera Grill doesn’t sound like much given the size of the glasses, but as they say, good (strong) things come in small packages. We were giddy. Trying to get him to reveal, what we call in Korean, ee-cha (the second car in a train of nightlife stops) had taken at least half a block headed north on Clark, and after we finally did determine that “Why? Lounge” was really, “Y Lounge,” we erupted into another half block of happily buzzed laughter headed west on Ontario. It was a perfect evening for a black leather jacket, but a little windy.

the biggest mcdonald's i've ever seen
now that is super-sized

About halfway to a hard buzz, my inner F.O.B.-ulosa tourist took advantage of my weakened sensibilities, and I took a picture of a McDonald’s. I know. *shakes head* I’m not sure why I thought it quite important to stop and snap a photo of a McDonald’s in the River North district of Chicago, but I am guessing that at the time, I believed it to be the largest McDonald’s I’ve ever seen. Super-size, really. No one, not even our very gracious host of the evening whom I’ll just call The VIP from now on, batted an eyelash. Either they had already been blinded into silence by my flashbulb fantasy at Frontera, or they were as nonsensically buzzed as I was, or they just thought that cute little LA girl hasn’t seen very many McDonald’s. LOL! Of course I have. I’ve just never seen one quite so…*gasp!* for the melodrama…ginormous.

On the way to Y Lounge, The VIP pointed out Portillo’s and Al’s Beef as possible stops for my daytime gastronomical tour of Chicago the next day. I nodded in appreciation for the recommendation knowing full well that there was no way I’d remember them in the morning.

Y Lounge is on Ontario, in an area that has quite a few bars, clubs, and lounges. Soundbar is next door; Spy Bar is around the corner. You might not find Y Lounge if you don’t know to look high for a glowing yellow “Y,” but at least you’d know you found it when you run into the big dude in the leather jacket out front. Now I’m not big into the guestlist game. Dressing to impress the bouncer, adopting an air of heiress entitlement, flirtation bribery, people in line when there are seven people inside the club – it’s all very stupid to me, and very L.A., but apparently, such pompous circum-dance is not limited by geography. They play the game in Chicago, too. Luckily, we just happened to be with The VIP, and sashayed up the stairs, passed the coat check for priorities – the bar.

y marks the spot
y marks the spot
y lounge, chicago, IL - dirty martini
filthy. delicious.

I thought drinks would be cheaper than the ridiculously over-inflated prices in LA, but they’re about the same, at least at Y Lounge. We started – LOL! I can’t believe I just said I “started” when technically, my count for the evening was already at six – we started with martinis all around, except my citron/soda. I tasted the martini, which was absolutely filthy delicious, but I can’t order martinis in a crowded lounge that’s playing move music. Half of the precious elixir splash-bounces right out of that highly stylish, yet utterly impractical glass. I can do a martini at dinner in a restaurant. Maybe even seated at a quiet bar. In a lounge rubbing up against strangers that would otherwise raise a perfectly plucked eyebrow? Not on my beloved little olive’s life.

We eventually checked our coats, so many black leather jackets becoming dangerously prone to mass static-shock. Besides, Y Lounge is a place to flaunt like you’re not trying to. Along the front wall, you and your metro date can drape yourselves for a Calvin Klein spread on low leatherette seats, though I don’t remember if they were actually leather. The marble-topped bar runs along the right wall, providing a place to perch your elbows when you’re pressed backwards up against it. It glows golden from underneath, meant to be ooh-la-la, but all I could think of when I placed my cocktail on it was marble pound cake. LOL! The bar faces what looks like the main “lounge” area with the same low seating set up in adjacent miniature sitting areas. When I innocently suggested we sit down (we did walk, after all), I was promptly alerted with a look and a raised matrini glass pointing toward the front of the lounge area – there’s a security guard separating the nightlife bourgie from the plebes. The funny thing is, there were no bourgie out. The main lounge was pretty much empty. A waif dressed in all-white (that’s my outfit!), wife-beater tank top, micro mini skirt, very-trendy-for-now ankle boots, and a hat oocasionally made an appearance on what appeared to be a shelf that couldn’t have held her if she weighed an ounce more. She was a dancer, I think. Club-provided eye-candy. Otherwise, a very drunk bourgie.

We engaged in conversation as if we hadn’t just spent hours at Frontera Grill catching up already, and even engaged total strangers in conversation. About halfway through it all, I politely excused myself, presumably to, well, go to the bathroom, but in reality, to do “the rotation.” It’s stupid, but it has to be done. I hate it. It doesn’t matter when or how many times, but “the rotation” has to be done. I headed toward the back of the Y Lounge for the ladies’ room, passing out tight-lipped smiles that hissed “Don’t talk to me” along the way. Get over yourself, Metroboy, I’m not looking at you. I’m old enough to be your…babysitter. Like fifteen years ago! The crowd
at Y Lounge is young.

The bathrooms are nice, and that’s all I need to say about that, because that’s not really what we’re there for. The bathroom? Please. Scoot over girl, I need to gloss. Lip gloss. Now complete the rotation.

We made it through two martinis, a rather short stay for ee-cha, but The VIP had plans for us. He grabbed our coats and as we headed toward the stairs that led down to the street, I took one last look over my shoulder. Yeah, it’s kinda L.A., but I’m used to it.

redhead piano bar, chicago, OL
flirty, just like some others i know

The VIP led us up Ontario, and about 5 blocks east and exactly 180 degrees in the opposite vibe direction from Y Lounge, we ended up at The Redhead, a piano bar. The dude at the door checked our IDs with a thank you and we ducked down the stairs of what felt like a very large converted basement rec room, low lights, dark wood, and swirling cigarette smoke. From just inside the front door at the bottom of the entry stairs, I saw a fairly sizeable circle of people with backs to us, seemingly pressing themselves en masse into the corner. They were actually seated around the piano. I couldn’t tell if they were one big group, or a bunch of strangers that were just really drunk, but people had their arms around each other, some with glasses raised in the air, all of them belting out Sweet Caroline at the top of their smoke-filled lings right along with the piano player. It seriously looked like the ending scene to some cheesy, feel-good ‘80s movie.

We passed the U-shaped bar in the center and sat down at a high table toward the rear. It was pretty crowded and rather raucous for mid-week, especially so late at night. Another set of martinis all-around and suddenly, the whole bar burst into song and dance. It was a piano version of You Shook Me All Night Long. I am not joking, the piano man was playing AC/DC. I feared for the fate of our martinis as middle-aged (*gasp!* wait, no, I’m middle aged!) Dockers-clad frat-boys-turned-accountants bounced and swung in ever-widening circles with the pastel twin-set who had kicked off their sensible shoes. I actually couldn’t tell if the crowd was mostly locals or tourists, because with servers dressed up like Vegas casino cocktail waitresses and bartenders in shirtsleeves and bow-ties, it almost felt like a tourist bar at the Epcot Center. I wanted to roll my eyes at how horrible the piano player was. I wanted to cringe at how cheesy this Disney musical version of You Shook Me All Night sounded. I wanted to turn my back to these stupid, annoying, obnoxious, drunk and immature overgrown muffins dancing around my table, but I couldn’t. I laughed instead. It was so bad, it was funny. Ridiculous.

One more martini through a slightly less painful rendition of Bon Jovi, then we called it a night. You know why Chicago nightlife is awesome? Because you can stumble ten blocks back to your hotel at 2 am.

Y Lounge
16 West Ontario Street (between Franklin and Wells)
Chicago, IL 60610

The Redhead Piano Bar
224 West Ontario Street (between Dearborn and State)
Chicago, IL 60610

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{ 7 comments… read them below or add one }

1 paul November 18, 2005 at 12:27 am

The mega-McDonald’s in the heavily touristy area is the former site of the “Rock n Roll” McDonald’s, torn down, apparently, to build that monstrosity to fit in even more tourists.

Please don’t get the impression the Y is typical of a Chicago club. It’s one of a few Chicago lounges which strives to be LA-ish. I shouldn’t be beautiful enough to get in to any of them.

I think the attitude at Y, Spy, and a few others is kind of like the attitude you get at Ed Debevic’s Diner (around the corner) where the waitresses dress up in 50’s skirts and big hair and give the customers a comic hard time – it’s an act when the doorman gives you a hard time and won’t let you in without waiting. That way you feel like you’re getting your money’s worth when you pay 15 bucks for a martini.

How do I know it’s an act? Cause if it was a real LA or NY VIP lounge I’d never be let in.


2 sarah November 18, 2005 at 2:19 am

lol! paul, you just made me lol! i don’t even want to know what the rock n’ roll mcdonald’s was all about. ok. i’m sick. rock n roll mcdonald’s?

y wasn’t really all that bad. a little expensive, a little too PYT, but not horrible overall. i would say between the two, y lounge was probably more my taste than the redhead. but you know, there’s always a time for sweet caroline. lol!!!!

wondering…for future reference…what do you recommend?


3 paul November 18, 2005 at 9:06 am

Rock n’ Roll McDonald’s was just a touristy McDonald’s with some music memorabilia made out as exhibits. Kind of like a Hard Rock with Big Macs. The real local McDonald’s pilgrimage is the weird recreation of the first restaurant in Des Plaines.

Recommend a bar? That’s a tough question. I’d have to read through all your bar posts to figure out what you’d really like. One person’s good time, could be another’s hell hole.

Y isn’t that bad, I agree, but i work around there, and while I sometimes am in the mood for clubby places, they’re not always in the mood for me. Looking forward to what you thought of Spy Bar.

I recommend places that have real character. And there’s enough places with character around here that you probably could find whatever style of bar you’re in the mood for.

Within walking distance of where you went, I’d send you to Celtic Crossing for as real an Irish Pub as you’ll find on this continent, Club Lago for the defintion of a Chicago neighborhood tavern, Narcisse for a lushly comfy VIP lounge, Martini Ranch for, duh, martinis, Blue Chicago for, duh, blues… I could probably think of a few more excellent bars, but that doesn’t mean you (or I) would hang out in all of them.


4 Xericx November 18, 2005 at 10:11 pm

Hah…I went to Y, when I went to Chicago in May. Never knew I was an “upscale clientele”.

That McDonalds is cool..i had to snap a pic too !


5 Gravity December 14, 2005 at 6:55 pm

The name of the place is Y-Bar, not Y Lounge — maybe if you took a second to even get the names straight, you wouldnt have to spend so much time being a bitter, washed up, L.A. scenestress…

Stay there if you dont like Chicago.

Oh, and Spy Bar is the shit. However, for someone so “in the know” — showing up at 11 was a pretty stupid fucking move.


6 sarah December 14, 2005 at 7:07 pm

1. thanks for the clarification on the name, gravity, though i don’t think confusion about names makes me a bitter, washed up LA scenestress. i’m just that way anyway :)

2. i like chicago.

3. i’m not in the know about chicago nightlife at all. i think i learned a little in the two nights i was there, but i’ll learn more when i go back.

at least i didn’t end up at hard drive.



7 gravity December 15, 2005 at 7:24 pm

Yes, at least you didnt end up at Hard Drive — easily one of the worst places to open up in the entire united states … its a hotel lobby with a rope and terrible music for fucks sake…

Anyway, let me know if there’s a way for me to email you so you have my email next time you’re in the windy city — I’ll make sure you know where to go. Oh, and I’m not some “JV promoter” — I’m actually a NYC transplant who knows whats up…


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