Webster's Wine Bar

Row 1

2601 N Milwaukee Ave (at N Kedzie St)
Chicago, IL 60647
(773) 292-9463
Wine Bar
$ $ $
Tue–Thu: 5:00 PM–1:00 AM Fri–Sat: 5:00 PM–2:00 AM Sun: Noon–9:00 PM

Foursquare Tips

  • Start with the Tuscan kale salad and then one of each of the Tapas, with maybe two of the cod and none of the peppers.
  • Drink this: Order by the flight and taste 3-4 wines in two ounce portions for $13-$17.
  • When tasting pours are this affordable (and interesting), we pretend its for educational purposes and stay all night, soaking up the dark, Bohemian vibe and munching on tasty cheese plates.
  • Webster's wine bar
  • Websters and Telegraph are sister bars, but at Websters the desserts are less complex. That doesnt mean the thin slice of pudding wasnt enjoyable. It left all the more room for another Madeira.
  • Off the beaten path but cozy enough to be a destination in itself. The focus is on small-production wines with a menu of snacks, flatbreads and cheeses to accompany them.
  • It seems pretty similar to what the space was like when it was Telegraph except the menu isn't focused on pasta. Oysters, grilled octopus and bay scallops were all really good.
  • The wine tastings are hosted by some incredible people. You're missing out if you haven't been to one.
  • Ask the servers for recommendations. Incredibly knowledgeable and very kind. Love this place.
  • The kale salad with anchovies. Craveable.
  • Stay loyal to your local bar, stay loyal to your local StreetWise vendor. Percy Smith is always selling!
  • Try Peninsula Cellars' Cab Franc
  • For $200 the Krug is a realtive bargin, same for the Salon 1985 for $500
  • Best and oldest wine bar in Chicago, hands down.
  • Runner up for Best Wine Bar presented by Segura Viudas at the 2017 Time Out Chicago Bar Awards.
  • Reasonable and generous taste portions are available at fair prices of their excellent wines.
  • Wine cheese board, and the meatballs.
  • The wine list is of course amazing but the service really sets the place apart. Don't be shy about setting a budget; there are tons of great, reasonably priced options!
  • A great lively place to try wine flights.
  • I admit I miss the old location, but this is closer, so I like o. DIY flight of 4oz pours is fun and educational. Skip a full meal and enjoy elegant small plates instead.