Webster's Wine Bar is one of The 15 Best Wine Bars in Chicago.

1. Webster's Wine Bar

8.9
2601 N Milwaukee Ave (at N Kedzie St), Chicago, IL
Wine Bar · Logan Square · 45 tips and reviews

Redeye ChicagoRedeye Chicago: 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. Read more.

Charles E.Charles Edge: 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.

Time Out ChicagoTime Out Chicago: Drink this: Order by the flight and taste 3-4 wines in two ounce portions for $13-$17. Read more.

Joe's Wine Cellar is one of The 15 Best Wine Bars in Chicago.

2. Joe's Wine Cellar

8.7
2108 W Division St (Hoyne), Chicago, IL
Wine Bar · Wicker Park · 13 tips and reviews

Anna A.Anna Amelia: Love they are always changing their wine selection. Delicious rose that the boyfriend actually selected... I created a monster...

Ana A.Ana Arrendale: It’s just an overall good place. People are wonderful, suggestions are on point

Mat B.Mat Burnett: Doing some research for my memoir, "Chillin' with Bacchus."

Easy Does It is one of The 15 Best Wine Bars in Chicago.

3. Easy Does It

8.9
2354 N Milwaukee Ave, Chicago, IL
Wine Bar · Logan Square · No tips or reviews
The Press Room is one of The 15 Best Wine Bars in Chicago.

4. The Press Room

8.6
1134 W Washington Blvd, Chicago, IL
Wine Bar · West Town · 1 tip

Josh B.Josh Broadhurst: Get the Amaro Nonino

Pops for Champagne is one of The 15 Best Wine Bars in Chicago.

5. Pops for Champagne

8.3
601 N State St (at E Ohio St), Chicago, IL
Wine Bar · Near North Side · 114 tips and reviews

Andrea N.Andrea Navarrete: Great place to have a nice champagne cocktail, great to a calm night out with friends so you can talk and enjoy your drinks.

Leyla A.Leyla Arsan: Indulge in something by the glass that you normally would not have!

Juicy CoutureJuicy Couture: This spot has over 100 champagne selections and lovely live music- try the Laurent-Perrier Demi-Sec for a sweet treat.

Figo Wine Bar is one of The 15 Best Wine Bars in Chicago.

6. Figo Wine Bar

8.3
3207 N Sheffield Ave, Chicago, IL
Wine Bar · Lakeview · 2 tips and reviews

Kay B.Kay Burnett: Nicely designed with wood and steel and brick. All sharp corners & hard surfaces so v.noisy.

JinSoo H.JinSoo Huh: Post show drinks w previous,‘Michael Victor

DiSotto Enoteca is one of The 15 Best Wine Bars in Chicago.

7. DiSotto Enoteca

8.1
200 E Chesnut St, Chicago, IL
Wine Bar · Streeterville · 13 tips and reviews

Yvonne H.Yvonne Holden: DiSotto is a wonderful wine bar that opens daily at 5pm. It's a late night spot for late night people. Great wine, great staff, what else could a person want?

Time Out ChicagoTime Out Chicago: Old World wine list and Mediterranean small plates: Scott Harris has nailed the formula at Purple Pig and Davanti Enoteca, so why mess with a good thing? Read more.

Raghav C.Raghav Chadha: Meat/salami platter is great and bigger than you think. Comes with great bread. Prosciutto and Coppa were great, wasn't a big fan of the Ndujo.

Volo Restaurant Wine Bar is one of The 15 Best Wine Bars in Chicago.

8. Volo Restaurant Wine Bar

8.0
2008 W Roscoe St (at N Damen Ave), Chicago, IL
Wine Bar · Roscoe Village · 14 tips and reviews

Redeye ChicagoRedeye Chicago: Seasonal tasting events, vino on tap and a beautiful backyard patio make this wine bar a prime place to unwind with whatever bottle you choose to uncork. Read more.

Mary Kay H.Mary Kay Hardcastle: one of the best wine bars in Chicago & a great date place

Courtney P.Courtney Persha: The lamb taco and the black and blue are fantastic!

Enolo Wine Cafe is one of The 15 Best Wine Bars in Chicago.

9. Enolo Wine Cafe

8.2
450 N Clark St (at E Illinois St), Chicago, IL
Wine Bar · River North · 16 tips and reviews

Brooke K.Brooke Krueger: Second time here. Came in for my birthday with my friends. Staff was amazing and on point. So knowledgeable about every aspect of the menu. They even brought out macaroons as a special treat.

AnneAnne: The Tiki Sauvignon Blanc is my favorite wine here

GwynneGwynne: Bruschetta

Cira is one of The 15 Best Wine Bars in Chicago.

10. Cira

7.9
200 N Green St, Chicago, IL
Wine Bar · Fulton Market · 16 tips and reviews

Manoj A.Manoj Ambalavanan: incredible vibe - great place to start or end your night. great shareables for food

Angeline C.Angeline Chen: I still dream about the fried olives - don’t miss them!!

Thierry L.Thierry Levenq: Also a nice place for breakfast

Uvae is one of The 15 Best Wine Bars in Chicago.

11. Uvae

7.3
5553 N Clark St (Bryn Mawr Ave), Chicago, IL
Wine Bar · Andersonville · 3 tips and reviews

Kathleen C.Kathleen Creagan: Great ambiance. Progressive, but familiar menu, nice wine selection. The deviled eggs and mole zucchini are a must!

Paul G.Paul Grisdale: Cozy wine bar opened summer 2019

Gil S.Gil Shepherd: Small plates

Outside Voices is one of The 15 Best Wine Bars in Chicago.

12. Outside Voices

7.6
3204 W Armitage Ave (Kedzie), Chicago, IL
Wine Bar · Logan Square · No tips or reviews
404 Wine Bar is one of The 15 Best Wine Bars in Chicago.

13. 404 Wine Bar

7.3
2852 N Southport Ave (at W George St), Chicago, IL
Wine Bar · Lakeview · 8 tips and reviews

Brenda Gail T.Brenda Gail Teruel: super cute place. perfect atmosphere & excellent for a first date.

Heather G.Heather G: Don't get the "prosciutto" - it tastes like lunch meat ham.

Brad S.Brad Saxon: Side note: if you do have a date on a Friday night here and are not sure how it went, stop in on Saturday and ask the bar tender how she thinks it went. She'll give it to you straight.

Eno Wine Bar is one of The 15 Best Wine Bars in Chicago.

14. Eno Wine Bar

7.3
200 N Columbus Dr, Chicago, IL
Wine Bar · The Loop · 5 tips and reviews

Teri P.Teri Pytel: Pomegranate, hazelnut, cinnamon toffee chocolates. Yum.

Mike W.Mike Wilder: Service industry discount daily - purchase any wine and receive a selection of 3 cheeses and 3 cured meats.

KasparsKaspars: No snacks and just a couple of beers.

ENO is one of The 15 Best Wine Bars in Chicago.

15. ENO

7.1
505 N Michigan Ave (InterContinental Hotel), Chicago, IL
Wine Bar · Streeterville · 21 tips and reviews

Gary R.Gary Render: Excellent chocolate flight pairing with the cote du rhone!

Time Out ChicagoTime Out Chicago: California's Silvertap Wines created two custom blends for the bar: a white blend of sauvignon blanc and chardonnay, and a multivintage red blend of merlot, cabernet sauvignon and a little zinfandel. Read more.

Leyla A.Leyla Arsan: The names of the flights are silly, but worth trying none the less