404 Wine Bar

3.5 star rating
97 reviews Rating Details

Category: Wine Bars  [Edit]

2856 N Southport Ave
(between George St & Wolfram St)
Chicago, IL 60657
Neighborhood: Lakeview
(773) 404-5886
Hours:

Mon-Tue 5 pm - 11 pm

Wed-Thu 5 pm - 12 am

Fri 5 pm - 2 am

Sat 5 pm - 3 am

Sun 5 pm - 10 pm

Parking:
Street
Accepts Credit Cards:
Yes
Price Range:
$$
Good for Groups:
Yes
Outdoor Seating:
Yes
Music:
Juke Box
Best Nights:
Fri, Thu, Sat
Happy Hour:
No
Alcohol:
Full Bar
Smoking:
No
Coat Check:
No
Noise Level:
Average
Good For Dancing:
No
Has TV:
No
Wheelchair Accessible:
Yes
About This Business:

We specialize in interesting wines from around the world, with an emphasis on small production, organic and biodynamic farming.  We offer many wines by…   read more »

Review Highlights   

  • user photo
    "Jack's/404 is one of my favorite local restaurant options." In 29 reviews
  • user photo
    "...a fifth star: they have a great selection of board games." In 6 reviews
  • user photo
    "It has a great wine selection and a cozy atmosphere." In 7 reviews
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97 reviews in English

  • Review from Kathryn W.

    Chicago, IL

    4.0 star rating
    2/3/2012

    I really like this place. It is right in my neighborhood and I can always find a spot at the bar. A good wine list but plenty of beers for my wine adverse fiance. its quiet and dimly lit without being overly romantic. The service has always been on point! I like my wine served with a smile.

    The only reason I reserve the last star are 2 reason: I have always had to enter through Jacks Bar which is very loud and fratty. And last time I was there it was so cold they actually had a space heater in the middle of the floor.

  • Review from Gianni C.

    • 13 friends
    • 9 reviews

    Chicago, IL

    4.0 star rating
    12/27/2011

    This is a great neighborhood spot, as other reviewers have noted, but I wanted to make a special mention of the fact that they have a pretty decent party room in back.  It's attached to an outdoor patio as well.   If you're looking for a good place to have a b-day party or luncheon, the combo indoor/outdoor space would be great in the summer.  

    The wine bar itself is very cozy and I've always found the staff and food to be great.  The newly remodeled outside is nice as well.  Hope they're in the neighborhood for a long time!

  • Review from Kris R.

    Chicago, IL

    4.0 star rating
    12/1/2011 1 Check-in Here

    i came here on a tuesday with my sister.  it wasn't crowded at all of course, since it was a tuesday.  i ordered a few glasses of wine and my sister ordered a campari/orange, as usual.  the bartender was super nice.

    for bites i ordered the tuscan flatbread, which was surprising pretty good!  it was sweet from the berry "compote" which was actually just dried cranberries sprinkled on top.  and the flavor was there, it was just a bit too thrown together.  the savory came from the prosciutto and the egg.  it was pretty damn tasty.

    i would definitely come back on a low-key night, for a drink and an appy.  not loud, laid-back, and relaxing.  romantic if you sat by the fireplace.

  • Review from Adam Z.

    • 0 friends
    • 1 review

    Chicago, IL

    1.0 star rating
    5/15/2012

    As of today, their website says $20 bottles of select wine on Monday.  No such special exists.  Beware the bait and switch.  And the wine is just ok with stingy pours.

  • Review from Zach A.

    • 0 friends
    • 3 reviews

    Chicago, IL

    2.0 star rating
    4/9/2012

    Good: Quiet, nice setting, attached to jacks, good selection of wine.

    Bad: I've been drinking wine for years and am quite experienced, there is nothing more obnoxious than having a bartender that 'knows it all,' grabs your (friends) glass, and proceeds to explain why his technique is wrong.  I don't care what you've been taught in your 2hr wine tasting class but swirling is good for looking at the legs of the wine, aerating, releasing scents, etc...

    While the unsolicited advice may have been good intentioned, I do not appreciate constant complaining about the lack of patrons or additional lessons on how and what glass to consume wine in.  Cater to your customers and let us enjoy our wine, don't annoy us with your rants, complaints, unsolicited (and incorrect) advice.

    I've read some great reviews so I'm attributing my experience to a pissy bartender who didn't get that many tips (wonder why?)..

  • Review from Tim R.

    Chicago, IL

    3.0 star rating
    7/18/2011 1 Check-in Here

    This place definitely has promise. It's attached to Jack's, which has a large outdoor space, and both places let you order from one another's menus. While Jack's was packed and energetic, 404 was very quiet and laid-back.

    The service was fine, but unfortunately the four wines we sampled weren't great. The California flight showcased three wines which, frankly, California is not great at producing. I'm no expert, but think I could have assembled a much better wine list and set of flights myself. Maybe I was just unlucky -- will try again.

  • Review from Sara E.

    Jersey City, NJ

    3.0 star rating
    7/18/2011

    I would like to give 404 3 and a half stars, but I'll deal. This place seemed really cute and was quieter than it's attached brother, Jack's.

    Wanted to sit on the outdoor patio at Jack's (you can order from both 404 and Jack's menus), but apparently everyone else in Lincoln Park had the same idea as me.

    Sat inside, the waitress was sweet, but the sparkling wine recommended was sickly sugary and not at all what I had told her I preferred.

    I'll give them a second shot, but will be a bit more skeptical this time, and will definitely do some research and choose my own drink.

  • Review from Joel M.

    Chicago, IL

    2.0 star rating
    5/22/2011

    I was disappointed by the place mainly because of the food.  I got the chicken and my wife ordered the pork chops - both were extremely dry and not really seasoned well.  At a wine bar, the food should be simple but still well executed and tasty.

    The wine was pretty decent, but a bit expensive ($12 a flight) for what you get.  We were recommended a more expensive bottle than what we originally wanted, went for it, and were disappointed (not really what we described that we liked).

    I will say the service was great and it has a wonderful ambiance, but those things can only take a place so far.  I'll go back to DOC or try another wine bar in the area before considering coming back here.

  • Review from Liz P.

    Chicago, IL

    4.0 star rating
    9/27/2011

    The boyfriend took me here for my birthday--props to him for something a little more unique than typical dinner. It was great. As others have said, the ambiance is absolutely perfect--hardwood, dim lighting and the fireplace make it so cozy and warm. The wine list isn't huge, which is good (because it's not overwhelming) and bad (wished they had a bit more of a selection). Amber (?) was our server and she was super perky and helpful in assisting us with our wine selections. It's a bit pricey per glass but sometime it's fun to splurge. I'd recommend this place to others, especially if you want to show someone special a good, unique time.

  • Review from Georgia K.

    • 27 friends
    • 67 reviews

    Chicago, IL

    3.0 star rating
    4/18/2011

    404 is A-OK. It's a decent little wine bar-- nothing spectacular.

    The wine list was a bit limited. I ordered the Portuguese wine flight (really good) and the California flight (ok). I thought it was strange that 404 is attached to Jack's Bar and you have to walk through it to get to the wine bar. We ordered a margherita pizza from Jack's menu, and it was pretty good. Our waitress was sweet and accommodating.

    All in all, an A-OK experience, but not my fav wine bar.

  • Review from Caroline M.

    Chicago, IL

    3.0 star rating
    5/31/2010

    Put all fancy preconceived ideas of wine bars behind you.  This place has got nothing on Bin 36, Webster's, etc.   I did, however, warm up to it towards the end of the night (hello, prosecco!)  It's a great location, comfortable seating area, nice ambience, and a pretty good wine list.  What was missing?  

    The food.

    We were told we could order off the Jack's menu, which is the attached bar next door.  Or we could have something from the very limited 404 menu, which was cheese, charcuterie, and a couple entrees.  We decided on cheese and to share one of their entrees (scallops).  The cheese presentation was lovely--apples, jam, bunch of grapes, crostini, and cheese arranged on a wooden platter.  

    Maybe I'm just a snob, but I'd like to see a few more options on the food end.   404 isn't the best wine bar in town, but if all you want is wine and cheese, then you'll love it.

  • Review from Stacy Y.

    Chicago, IL

    1.0 star rating
    8/20/2008

    I was all ready to book a bachelorette party dinner for 10...

    But they WON'T take reservations. Or hold tables. Or anything else. The person I spoke to told me to show up and then wished me luck finding a table.

    Am I missing something here?
    We wanted a nice, chill start to our evening (within walking distance of the bar where we'll spend the rest of the night). I can understand not taking resos. Okay, that's fine. But absolutely no accommodations for groups/large parties?!?! Really?

    Jack's & 404 wine bar - you suck.

  • Review from Aurore L.

    Chicago, IL

    3.0 star rating
    2/17/2010

    Let me use my favorite expression here, courtesy of Yelpette extraordinaire Erin P (yes, she is expending my vocab on a weekly basis...but seriously where else would I learn these things?!?!) : when it comes to 404 Wine Bar I am a
    :::::::ready?!?!?!?!:::::::
    "Debbie Downer".

    I dunno why. It has a lot to please, and it's trying hard but it just doesn't quite do it for me. I must be picky.
    I arrived last night early and sat on the leather couch just in front of the fireplace. Sweet, right?!?!?
    The waitress was a sweetheart, I had a good glass of petite syrah, a nice time with my friends....

    Still.

    I might have found a good wine option but wasn't overall impressed by the selection. It showed on the second round when I had the hardest time to find something I liked - even with the assistance of the staff.
    And the food....404 doesn't offer much. 5 cheeses, 4 meats and 4 appetizers. That's it. Pretty limited for a place this size and this classy. They also give you Jack's menu (the sports bar 404 is connected to) but who wants nachos, dips and burgers with their wine?!?
    I mean...I do...sometimes. But you get my point.

    There are so many other good wine bars in the city that I don't picture myself coming back here any time soon. Even if parking is easy.

    Yup. I am a Debbie Downer. And (almost) proud of it.

  • Review from Caroline A.

    Chicago, IL

    5.0 star rating
    1/30/2007

    Love this little neighborhood spot.  It is cozy, unpretentious and perfect for a cold winter night!  Service was very very fast, and our server was fantastic.  She gave good recommendations on wine (they have a small, but great selection of wines by the glass) and was great about checking up on us.  We started with the hummus plate... which was yummy.  We then had the margherita pizza.  Not your traditional margerhita - it tasted more like and had a texture of foccacia.  

    Will be back when in the neighborhood!

  • Review from Isla E.

    • 227 friends
    • 246 reviews

    Chicago, IL

    4.0 star rating
    10/30/2008

    The ambiance is as presented on the website (accurate). Its pretty cool how they have 2 sides, the sports bar and the wine bar. Plus the garden in back. Just so you know, you have to enter on the sports bar side and walk through to the wine bar. But all menus are available on either side, it just depends if you want to sit in a bar stool and watch TV or sit on a cozy sofa by the fireplace. They have some board games, that amenity alone is worth 2 stars in my book.

    I had a Chardonnay/Pinot combo and I don't care where it was from. If you can't find a wine to drink here then there is something wrong with you. The beer selection isn't the best but it isn't terrible. There a short, fairly conservative list of martinis. Nothing you haven't seen before, but really, what's it gonna be next? Martini on a stick? Funnel cake martini? So yeah, its just normal.

    The food is a little overpriced but it is good quality. The service was  stellar, really, waitress, bartender, busperson, all of them seemed genuinely glad to have us there. But the jukebox is not even worth figuring out, unless you miss Q101 circa 1990.

  • Review from Angela W.

    • 10 friends
    • 11 reviews

    Chicago, IL

    5.0 star rating
    7/26/2011 1 Check-in Here

    This place is perfect!  My husband & I went after dinner, so that we could spend more time together. Ambiance a 10+. Exposed brick walls, eclectic furniture, intimate lighting, smooth wine....made me fall in love all over again... And it was our first time there... Perfect. :)

  • Review from Paige W.

    • 386 friends
    • 196 reviews

    Chicago, IL

    5.0 star rating
    12/11/2007

    After a horrible experience at Christkindlmarket in Daley Plaza that left me chilled to the bone (see my review here: http://www.yelp.com/bi...), the boyfriend and I agreed on one thing: We needed red wine and a warm fire to sit by.

    Luckily, 404 Wine Bar has both. We hurried through the smoky anteroom, which is apparently a frat bar that specializes in draft beer, cell-phone drama in the bathroom and guilty pleasure top-40 music, and straight to the cozy "private room," where a leather couch near a fireplace beckoned to us.
    We enjoyed a lovely bottle of wine, a huge piece of homemade chocolate cake and warmed up by the hearth.

    Another couple, who had driven in from the far southern suburbs (if that drive doesn't speak for 404, I'm not sure what would), sat in two cushy leather chairs caddy-corner to ours, and we ended up chatting with them for an hour. Red wine, a fire AND new friends?

    What more could a girl ask for on a frigid winter night?

  • Review from Christina P.

    • 111 friends
    • 159 reviews

    Chicago, IL

    5.0 star rating
    6/20/2008

    Hands down, this is my favorite wine bar in Chicago.

    It's so quaint & cozy and the staff is very knowledgeable. I always prefer to sit in the front room near the fireplace. And, I love board games and 404 has a few scattered around there too! I love their menu - simple and easy to pair wine with. I completely recommend this place for a first date or a girls night out. Plus, you are close enough to other Southport based bars if you need to get out of wine-bar-mode & liven it up.

  • Review from mary e.

    • 60 friends
    • 139 reviews

    Chicago, IL

    5.0 star rating
    1/1/2008

    Let me start off this review by pointing out this is NOT a review of Jack's - the regular bar to which the wine bar is attached.  

    That being said, I love 404! This is a favorite of mine.  They have a decent selection of better than average bar food (i.e. - hummus and pita, quesadillas, etc).  The waitresses are always nice and never make me feel like a wine dum dum.  I am a wine dum dum (I know so little about wines it's embarrassing).  They take care to explain the wines to me. 404 also has a nice selection of beers, mixed drinks, etc.

    The bar has warm feel to it.  Lights are low but not obnoxiously low. Music can get loud when it gets crowded but I'm always able to hear my friends speaking to me.

    Basically - nice, cozy place for a glass wine and nice conversation.

  • Review from Lauren D.

    • 70 friends
    • 229 reviews

    Chicago, IL

    4.0 star rating
    12/27/2008

    Disclaimer: I am not including any comments on service because I am going to assume that the truly awful server we had was just a fluke - maybe new and inexperienced.

    Otherwise, great place to meet up with a friend.  I love the atmosphere and it's cool that Jack's is right next door, with a lounge type environment in the middle of the two.  Menu looks delicious for dinner and I've heard only good things about their food, although I only tried their artichoke cheese dip, which was delicious.  Extensive wine list, and the outdoor area is charming.  Love it!

  • Review from Juanita G.

    • 21 friends
    • 117 reviews

    Leiden, Zuid-Holland

    Netherlands
    5.0 star rating
    3/21/2007

    I had a great time with the girls here last week. We had gone to see a play and wanted somewhere to get a drink. We went looking for a place and drove past and I remembered the Yelp review I had read a while back.

    We ordered a bottle of champagne and some desserts that paired well. (There is no occasion to small for some bubbles.) The lighting is great and sets the tone for the coziness of the place. Our waitress was sweet and helpfully honest about the wines. We were a little crammed between 2 tables but we were able to chat and share our desserts. I'll definitely be back soon.

  • Review from LK P.

    • 0 friends
    • 114 reviews

    Chicagoland, IL

    4.0 star rating
    12/17/2010 2 photos

    Great place to cozy up with someone at the fireplace, or share a few bottles with a larger group.  Our group of 9 visited 2nd week of November.

    Nice, cozy place with an stylish bar area, couches and a fireplace, a patio area, and adjoining Jack's sports bar, but not intrusive, at least not by 10pm.  Casual but elegant.

    Everyone was so friendly and welcoming, and we were seated in the back room.  We had the syrah flight (usually love syrahs, but didn't like any of the selections), 4 vines flight (excellent, especially the tempranillo), but didn't care for their menu, so ordered off the Jack's one - cheesesteak and chicken sandwiches, which were just ok, but the sweet potato fries were yummy.  Their wine selection is varied enough both in varietals and region.

    Would definitely return.

  • Review from Tom L.

    • 3 friends
    • 14 reviews

    Chicago, IL

    4.0 star rating
    2/16/2007

    Love this dual offering. What? Here is what I mean. This spot is basically 2 bars . . . Jack's (typical Chicago pub) and 404 Wine Bar (speaks for itself).

    From what I can tell, 1 wall was seperating them and unknown to me, someone decided to eliminate the wall or merged the 2 to form a new combo.  Really the best of both worlds you might say!

    Highlight:
    Patio for the wine bar is worth the mention with low lighting created by lights strung wall-to-wall.

    Back room of wine bar offers cozy fireplace, tables and leather, cushy chairs and couches.

    The facts:
    Great social spot overall between the 2. Jack's offers you a typical beer and spirits scene with big screen and tv's to catch sports.

    404 Wine Bar is just a step away. This is my favorite and it gives you access to great flights, a wine selection that is ample for all and a good menu (light eats).

    Bonus, you get access to the bar menu of "Jacks", which offers burgers and typical bar grub if you are not into a cheese flight but a cheese burger!

    All in all, a 2-fer that satisfies your beer buds and your wine curious side!

  • Review from Ariel B.

    • 40 friends
    • 175 reviews

    Chicago, IL

    3.0 star rating
    7/30/2007

    The Wine Bar is pretty decent when it's not crowded. They've got some nice seating, a decent nosh menu and the service is OK.  The Wine selection is very good, tho.

    On the Jack's side of things, whoa nelly, not so great.  We tried to eat in there a couple of times, but we just felt like we were in the middle of a frat party.  HUGE television in the front of the bar, really just too big for the place.  We like sports and beer as much as the next person, but this is way too much.

    The only thing we found to be any good on the menu was the burger. Can't go wrong with a burger.  Skip the salads, it's only lettuce.

  • Review from Meghan P.

    • 139 friends
    • 309 reviews

    Chicago, IL

    3.0 star rating
    3/11/2009

    This place leaves me a little meh... I want to like it, but its just too pricey and pretentious for its own good.  I felt like its a bar fair of food, because you can order off the Jacks menu which is the pub connected to it so thats sorta confusing and the wine tasting wasn't the most thrilling of my life, because there wasn't a whole lot of variety.  

    Food is decent, wine is decent, but all this just being decent at those prices?  Sorry not so much a fan.

    I did give it three stars, because if you're not as cheap as me, live in the area or like a nice cozy atmosphere which I will give it props for then this is pretty ok.

  • Review from Steve T.

    • 100 friends
    • 274 reviews

    Chicago, IL

    4.0 star rating
    12/13/2009

    Great place to lounge around and sip some wine with friends.  Definitely a nice lower-key option, though more pricey, than going out to a crowded bar or club.  Over the course of a few hours we drank 4 bottles of wine.  Yes, we're alcoholics, deal with it.  

    One of my friends ate a salad here and loves their blue cheese dressing... so much so that she proclaimed she could eat a vat of it.  I would like to see this happen, so if anyone can get us a vat of the dressing.... I know what my friend will be getting for Christmas.

    The only downside was it did start to get quite crowded and it seemed our waitress had a large area to watch over so sometimes it took longer than we had liked to get our next bottle.  However, this probably paced us, soooo I'm not complaining too much.

  • Review from Tony S.

    • 29 friends
    • 38 reviews

    Los Angeles, CA

    4.0 star rating
    9/2/2007

    I didn't know what to expect coming here. It is not a neighborhood i would go to hang out in. i went to the 404 Wine Bar.

    However, I met up with a group of about 12 people on the back patio on a Friday night and I had a really good time.

    My friends were mostly drinking wine, but they had a huge selection of stuff to pick from and they even had $2 PBR's in a place I thought a little more high scale than that. I had quite a few.

    I also ate the best steak sandwich I have ever had!!!!!!!!!! it was 13$ but it was delicious and not a piece of fat was on it. It went down smooth, and it definitely left an impression. The staff was nice too. If you are looking for a nice place to sit outside with your friends, i recommend it.

    I probably wouldn't go to the Jacks side though because everybody looed the same and it wasn't my crowd.

    So you don't think i am a neanderthal, I assure you, that I drank the PBR from a wine glass.

  • Review from Linds R.

    • 20 friends
    • 123 reviews

    Chicago, IL

    3.0 star rating
    2/13/2009

    So, the search for a rehearsal dinner spot continues. I won't drag all of yelp into the family drama, but this is the spot that Mister's parents are gunning for. I don't get it.

    We came on a Tuesday night, and the girl that handles the bookings or whatever was nice enough to send over a dessert and appetizer, but I didn't really like either one..so...I guess thats a moot point.

    I did have a shitteous day at work that day, so maybe that is clouding my judgment, but the food was very generic. I disliked having to walk through the red-bull-and-vodka smelling bar (Jacks) to get to the space, and the meal was very forgettable.

  • Review from Jess R.

    • 5 friends
    • 13 reviews

    Chicago, IL

    4.0 star rating
    4/4/2008

    I've only been here once, but I really enjoyed it.

    They have a great selection of wines - either by the glass, bottle, or flights. I love wine flights! :o)   I was there late fall and the fireplace def. kept us warm while we enjoyed our bottle!

    I'll be back again, i'm sure.

  • Review from Amanda C.

    • 4 friends
    • 17 reviews

    Chicago, IL

    3.0 star rating
    2/11/2008

    I have been to the 404 several times and I always have a good time.

    My first visit was after a nice dinner with some friends. We did not want to head home and we did not want to go crazy. We decided share a nice bottle of pinot grigio at the 404. Great atmosphere and we could hear each other.

    I have also had dinner here and the food was decent and reasonably priced.  I would come back for the wine ...not necessarily for the food.

  • Review from Christina B.

    Chicago, IL

    2.0 star rating
    2/8/2010

    I think I hyped this place up too much in my own mind. I mean, by the sounds of the descriptors--candlelight, exposed brick, plush couches, fireplace, cheese and wine--this place sounds like a recipe for a swell night.

    And all of those things are present. I liked the atmosphere (you could pretty much add a fireplace to Alcatraz and have me swooning). But my biggest problem was with the menu--it's all over the place. It's clearly just re-purposed bar food (it shares the space with Jack's Bar & Grill). Oh, and then there's another menu, with wine, and some random appetizers, but no entrees or beer. Those are on the other menu. So there we sat, in what felt more like darkness than candlelight, with 33 menus feeling a little lost.

    I can't say the service helped those feelings. Our waitress dragged. She was no help in our food/wine selection (and by no help, I mean we had to remind her that they actually had a soup of the day), and she kind of didn't care when someone mentioned that the $12 beer they'd ordered tasted a little flat (her exact response was, "Well, do you want something else?").  To be honest, the only reason we got a food order in was because I realized the "crowded" feeling at our table was a direct result of the 33 menus still being on our table almost 45 minutes into our seating.

    The wine I chose was pretty awesome, though (Revolution 9?), and the baked brie app was tasty. I had french onion soup, which I can only remember as being mushy. And the margherita pizza was decent at best. The guys all seemed to like their sammiches (bonus for the sweet potato fry option), but all in all, I think we all walked out and sighed a collective "meh".

    I wish they'd revamp the menu--more wine flights and tailored dishes to those patrons who choose to dine at a wine bar, not a bar and grill. It's worth a try, but I don't know if it's worth a return.

  • Review from Matt M.

    • 17 friends
    • 33 reviews

    Chicago, IL

    3.0 star rating
    10/12/2009

    Didn't have a very positive or negative reaction to 404 Wine Bar, it's just OK (hence the 3 stars).  I had their special (a pasta dish w/ parmasen cheese sauce and chicken) which was completely underwhelming and bland.  Their fries are excellent though so maybe I should have stuck w/ the pub food part of their menu.

    If you are looking for a quiet 'wine bar' experience, though, this may not be the place to go.  It was annoyingly loud and impossible to have a conversation unless you were willing to yell to your friends sitting three feet away.

    Redemption for 404/Jacks is their beer selection which is extensive and unique.  Three Floyd's Gumballhead is a personal favorite and they stock it.  I also tried one of their 'Hobgoblin' beers that was served in a custom goblet.  Very cool.

    Can't say it was a bad experience by any means, but I just couldn't rave either.  A-OK seems fitting.

  • Review from Lindsay A.

    • 9 friends
    • 45 reviews

    Chicago, IL

    4.0 star rating
    11/21/2009

    Boyfriend and I headed up to 404 Wine Bar last night after we passed it on the road a few days earlier and said "that place looks sort of neat."  We got there around 7pm (friday night) and immediately found a place at the bar.  Not 15 minutes later every seat in the house was full... we were feeling pretty good about our idea.  The place is small, and dark, a perfect fall/winter bar where you can go get cozy for a few hours and a few glasses of vino.  The bartender allowed me to try 4, yes 4, wines before I decided on one (yeah, i have a bit of a decisive-ness issue).  He was super nice about it and when I apologized for being so indecisive he assured me that he was happy to do it (don't worry, we tipped him like Rockefellers.)

    The wine was great, and i really, really enjoyed sitting at the bar.  There's also super cozy fireside couch seating that would be perfect for a first date.  The only downside (and star detractor) was the food.  We ordered the squash ravioli to split, and it was just missing something.  It was in this alfredo sauce, which i found sort of unexpected, and not in a good way.  There was no pizzazz to it... even just a hearty sprinkling of parsley might have done the trick.  But that's ok, next time we'll try something else.

    OH, they also have games, we played connect 4 for awhile, and as it turns out.... i'm really bad at that game.

    all in all a great little spot if you're looking to get out of the hustle bustle of the city and relax with a glass of wine and some good conversation.

  • Review from Beth M.

    • 35 friends
    • 21 reviews

    Chicago, IL

    3.0 star rating
    1/17/2010 1 Check-in Here

    Nice wine list, with plenty of selections by the glass.  Prices are okay.  Bartenders knowledgeable and helpful if you are searching for a recommendation.  Food selection is limited but elegant (gourmet cheeses with crusty bread, butternut squash ravioli that I can't wait to try).  

    404 is connected to Jack's Sports Bar, making it easy to shift vantagepoints from cozy seats by the fire with a glass of Pinot Noir to a hightop table with the game on and a pint of draft.  The servers are great about letting you move around and transferring your tab.  Jack's food is ordinary bar food, and is average, from what I have had.

  • Review from Kate H.

    • 4 friends
    • 28 reviews

    Chicago, IL

    2.0 star rating
    1/10/2010

    Just call me a glutton for punishment.
    I have been here four separate times now and every time I am let down.  You can get better value for your money at Webster Wine bar or even at the wine bar at Whole Foods on North Avenue. The service here is consistently slow and you strangely have to walk to Jacks to get into this place. The food is also just okay.  The most redeeming quality of this establishment is its very enjoyable patio/beer garden... which means it will probably lure me back here when the weather gets nice again. Look for an update when Chicago thaws...

  • Review from Eduardo M.

    Chicago, IL

    4.0 star rating
    6/15/2010

    We came here for dinner the other night, kinda on a whim.  it was a weeknight, early evening, so the place wasn't too crowded.  

    The dinner choices were excellent.  Not gigantic portions, but they leave you satisfied and happy.  I had scallops with lima beans (I think they were limas) and tomatoes.  Excellent choice.  I felt like I ate something that the chef made for himself and decided to share.

    I didn't try the wines (yeah, I know..) but the selection seemed decent.  

    Overall, I'd recommend this place, and I'll definitely be back.

  • Review from vivian h.

    • 1 friend
    • 29 reviews

    San Francisco, CA

    5.0 star rating
    5/9/2007

    I've got 3 words for you: chicken pot pie.

    My friends and I used to always go to 404 when the first snowfall hits Chicago. The CPP is amazing and makes you feel nice and warm. It's a hearty meal and I dare you to try and finish it! The cheese flight is marvelous as well as the artichoke dip.

    The restaurant is extremely cozy, especially when you sit in those comfy couches next to the fireplace. There's also a back room that combines another sofa with tables...the whole place feels like you are in someone's study - very relaxing and informal.

    Go check it out, it's a great neighborhood hang out!

  • Review from Leigh R.

    • 11 friends
    • 29 reviews

    Chicago, IL

    5.0 star rating
    3/13/2008

    I almost didn't want to review 404 bc I love it so much, I just didn't want to share.  I don't want to get too wordy so here it is:

    Wine
    Cheese
    Fireplace
    Wine
    Chicken Pot Pie
    Wine Flights
    Cheese
    Board Games
    Wine

    That's all.  You can fill in the rest yourselves.

  • Review from Chris L.

    Chicago, IL

    3.0 star rating
    3/3/2010

    It had been a while since I had gone to 404.  I went with my boyfriend to redeem a groupon we had.  First off, their wine by the glass list is fairly limited.   Nothing really caught my eye at the time.  Although they do have $20 bottles on Monday nights.  Their food is not to bad.  They have a good selection of appetizers and entrees and the price point is fair.  I had a pizza which looked homemade and tasted pretty good.

    Ambiance is nice.  When we went, it was pretty quiet and service was great.

  • Review from Melissa R.

    • 205 friends
    • 228 reviews

    Chicago, IL

    5.0 star rating
    9/16/2008

    This place is perfect for a low-key evening (especially during the colder months), and it's great for dinner with a friend or a date.  The decor and lighting are very welcoming and relaxed, but at the same time elegant.  The wine list is pretty extensive and the menu is somewhat small but delicious.  

    The service was really friendly and helpful.  One of my favorite things about this place is they let you stay as long as you'd like without trying to push you out.  The reason this earned a fifth star: they have a great selection of board games.

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