Last Updated On: October 16, 2017

I personally love drinking wine all year long but there’s something really cozy about going to a wine bar during the cooler months. Since fall is almost here I thought it was the perfect time for this girl’s guide. I love sitting by the fireplace (a huge bonus if they have one) sipping on some great wine, while enjoying a selection of delicious cheeses. Sounds so good right?!

So, if you are a wine lover like me you will love using this girl’s guide to enjoy some of the best, coziest, chic, and fun wine bars throughout the city.

ENO on the Mag Mile

Eno is located in a great location on Michigan Avenue. This is a fun spot to go to and relax after a long day of shopping. They have a great selection of wines along with cheeses and chocolates and a menu with small plates to share. Eno also has a happy hour Sunday through Thursday featuring 50% select wines by the glass. Looking for a wine tasting? You can sign up for Enoversity which happens once per month and it includes five wines with food pairings for $55.

Location: 505 N. Michigan Avenue

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Fig and Olive

Fig and Olive is inspired by the South of France. Fig and Olive is beautifully decorated and such a bright and cheery restaurant to enjoy a glass of wine or a glass of rosè with some shared plates any time of the year. They also have a garden rooftop patio that is definitely worth going to during the summer months. Fig and Olive also have a happy hour Monday through Friday 4 pm to 7 pm at the bar and in the lounge. A perfect place to meet the girls there after a long day of work.

Location: 104 E. Oak Street

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DiSotto Enoteca

DiSotto Enoteca means underground wine bar in Italian and that is just what this wine bar is! Located underneath Francesca’s on Chestnut this cozy, hidden gem wine bar even has stone walls. It is a great place to come and enjoy a glass of wine after an Italian meal upstairs. Their bar features over a hundred different wines and is open late, so it’s also perfect for a nightcap after a night out in the city.

Location: 200 E. Chestnut Street

Enolo Wine Cafè

Located in River North, Enolo Wine Cafè is a casual, modern wine bar with small bites, pizzas, and panini’s. They focus on wines from small vineyards and you can definitely enjoy happy hour Monday through Friday from 4 pm to 6 pm with $7 glasses of wine.

Location: 450 N. Clark Street

City Winery

City Winery has two great locations in the city. One on the Riverwalk which is so much fun during the warmer months, and another in the West Loop. The Riverwalk location is perfect for enjoying wine and people watching. Or you can head to the West Loop location for a fun girl’s night of live music and great wine. City Winery also offers daily and all day Sunday tours of the winery which include a wine tasting. Tickets are $50 per person but check Groupon before you plan your trip because they often have discount tickets.

Location(s): 11 Chicago Riverwalk1200 W. Randolph Street

Twisted Vine Chicago

Twisted Vine is a cute little gem in the Lakeview neighborhood. They offer so many fun events throughout the week. On Sunday’s they feature movies and games, live music Wednesday through Saturday and half-priced bottles of wine on Tuesdays. If you are looking for a free wine tasting they have one on the first Thursday of each month, starting at 6:30 pm.

Location: 3530 N. Halsted Street

DOC Wine Bar

DOC Wine Bar in Lincoln Park and has just recently been renovated. If you have been there before yes, they still have their cozy fireplace but the new look throughout the bar is a little more updated and trendy. They offer seasonal wine flights and a great wine list. Stop by on Sunday’s for $10 flights and Monday’s for 50% off bottles.

Location: 2602 N. Clark Street

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Willow Room

The Willow Room is located in Lincoln Park right next to the Steppenwolf Theatre and is the perfect cozy spot to enjoy a great dinner or a delicious brunch. The Willow Room also has an extensive wine list so you can pair a great wine with your meal. After dinner head down to the basement to relax and enjoy a nightcap.

Location: 1800 N. Halsted Street

Ada Street

Ada Street is a wine bar but you might also think it’s a speakeasy and you are not wrong. The building is very simple on the outside but inside you will find a cozy but fun restaurant space with a long bar for dining and drinking to match. It is definitely a hidden gem and it has a little something for everyone, great food, wines from Calfornia, and amazing cocktails.

Location: 1664 N. Ada Street

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Webster’s Wine Bar

Webster’s Wine Bar, is one of the oldest wine bars in Chicago. It’s the place you go to when you want to feel like you are going to a friendly neighborhood hangout with a little sophistication. They have one of the biggest wine lists in Chicago and they also have some fun specials throughout the week. Come on Sunday for a $12 burger and a glass of red wine. Monday and Tuesday a special bottle of wine is chosen by their sommelier and is featured at a discounted price (which I think is really cool).

Location: 2601 N.Milwaukee Avenue

BIN 36

If you are looking for a casual dining spot with great wine options then you should head over to BIN 36. They feature wine flights and a happy hour on Monday through Friday from 3:30 pm to 6 pm.

Location: 161 N. Jefferson Street

RM Champagne

RM Champagne is the wine bar you definitely need to come to and enjoy their beautiful garden patio during the summer months and cozy up by the fire during the winter. This bar is a great place to come for dinner or stop by late night for a glass of wine and enjoy a yummy dessert.

Location: 116 N. Green Street

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Rootstock Wine & Beer Bar

Rootstock Wine & Beer Bar is small and intimate bar located in Humboldt Park neighborhood. Enjoy food, wine, and beer with a focus small production and organic farming practices. Enjoy Spanish and French-influenced small bites and along with cheese boards and be sure to ask about their rare selection of wines by the bottle.

Location: 954 N. California Avenue

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A Girl’s Guide to 13 Amazing Wine Bars in Chicago



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Girl's Guide Chicago