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Websters Winebar1480 W Webster Ave, Chicago, IL | Directions 60614
41.921772 -87.666277
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“enjoyed the atmosphere--fairly quiet, small wooden tables and chairs with an assorment of art.”
“work in customer service and collect wine--I believe it should be a relaxed, enjoyable experience without any snobbiness or stress.”
“They now have great food to go with an amazing cheese list.”
“The servers are really helpful and knowledgable about the menu.”
“have no want to return to this establishment with so many other wonderful options here in Chicago.”
“The servers are really helpful and knowledgable about the menu.”
“There's no point in going into details on the wines - they have 40 by the glass that constantly change, they are consistently tasty, the prices are great, and you never see generic wines on the list (my big beef).”

You can get wines by the bottle, glass, or a tasting size that will allow you to try a lot more wines. Pair with small bites and flatbreads.

Self-coined as the oldest and finest wine bar in Chicago, I completely concur. Add quirkiest to the list and you've got the perfect place for a glass/bottle of vino.
Mindblowing wine list and the best servers in town.
Wow - I knew this was Chicago's oldest wine bar, but didn't know it was, by far, the city's best. I don't think any other wine bar in town has even HALF the number of wines Webster's does, and their prices are cheaper than anyone elses, too. Best of all, the servers are friendly and they know their stuff! Yes, the atmosphere is great, the food is delicious, and the service is top notch, but it's more than that - these guys really know their wines and are passionate while unpretentious. The owners even take their waitstaff to Europe every year to visit wineries and taste!! I mean really, who else in the entire country even does that???
There's no point in going into details on the wines - they have 40 by the glass that constantly change, they are consistently tasty, the prices are great, and you never see generic wines on the list (my big beef). They also have a great beer list (about 20 bottles) and a quality spirits list. The food is fantastic - not the largest menu, but everything is tight and goes perfectly with wine. For light bites, you can't beat their tapas selections (which include Italian and French traditional "bites" too), and their entrees are all classic regional dishes intended to pair with wines from the same region. And the food is inexpensive, too.
Bottom line: no other wine bar in this city really has taken it to the level Webster's has. If you haven't been to Webster's, you are missing the boat!
Great low key wine bar. Dark, romantic atmosphere. Try and snag a couch. A big wine list with great wine flights for sampling. The servers are really helpful and knowledgable about the menu.
Casual Lincoln Park alcove that doesn't allow wine snobbery..
The Scene
A dark, charming, European-style wine bar, where groups of friends lounge in cushy velvet couches and couples whisper over candlelit two-tops. Service is smart, friendly and quick with recommendations.
The Draw
More than 40 boutique wines by the glass and 400 by the bottle, from Spanish red 1996 Realeza in the $20 range to Dalla Valle (Maya Napa Valley) for more than $200. Every region is represented, though American and French reds are somewhat emphasized. Can't decide? Order a flight and taste three two-ounce servings of selected wines. Adventurous palates can design their own flight, or take advantage of premium pours (esoteric wines not normally featured), which change monthly. Munch on goat cheese fritters, mushroom bruschetta, smoked salmon and other wine-friendly fare, all reasonably priced, with most items less than $10. Or order one of three cheese flights.
Casual Euro-style bar, poor service and incorrectly stored products..
I enjoyed the atmosphere--fairly quiet, small wooden tables and chairs with an assorment of art. However, I was very disappointed in the service and how my party was treated. We had a diverse crowd with serveral wine-savy people in the group. We ordered among other bottles, a white Bordeaux, which was fizzy and nearly room temperature. No taste of the bottle was presented to the selector and everyone agreed that perhaps the wine had been subjected to extreme heat at some point during shipping or storage. We kindly asked if we would arrange for a different bottle or to have that one discounted so we could purchase another bottle; our waiter denied all attempts in a very terse manner. I work in customer service and collect wine--I believe it should be a relaxed, enjoyable experience without any snobbiness or stress.
Needless to say, my night was not enjoyable, save my company, they were all very well behaved.
I have no want to return to this establishment with so many other wonderful options here in Chicago.
Great Spot. Took a few out of town guest here and had a wonderful time. The atmosphere was great for conversation. Things were going on around us, but never interferred with our space. Jessie, the server, is amazing. She is knowledgeable about wine and scotch and was right on top of things all night long. Our group continued to grow and she was right along with us. It never felt like she was "waiting" on us, but there to help us have a good time. Can't wait to go back.
wine and staff. It has the best wine selection in town and you can buy every thing right next door till close. They now have great food to go with an amazing cheese list. If you ever are not sure just ask the staff is great.
Lucky times 2. Great place to end the evening. Last two times I was there things really started heating up and ended up continuing to do so in the wee hours of the morning. I'll be back.
Not for wine snobs!. The staff and the incredible selection of wine are what make this place special. The staff is knowledgable, but not pushy. They take the time to learn what you like and make an educated recommendation. Dark, quiet, candlelit, perfect place to go to after a movie at Webster place with a date or a friend. Also great appetizers--try the pear and brie quesadilla.
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