The 16 Best Old-Fashioned Chicago Bars

For those seeking a taste of old-fashioned charm in the heart of the Windy City, Chicago has several hidden gems to explore. From dimly lit taverns with classic cocktails to speakeasies with a prohibition-era vibe, these establishments offer a glimpse into the city's rich history.
Whether you're a local looking for a new haunt or a visitor craving a unique experience, this list of the 16 Best Old-Fashioned Chicago Bars will help you find the perfect spot to enjoy a drink and step back in time.
- Handcrafted cocktails with a vintage twist
- Cozy atmospheres with vintage decor
- Live jazz or blues music performances
- Knowledgeable bartenders who can recommend classic drinks
- 1. Old Fashioned Donuts
- 2. Three Dots and a Dash
- 3. Longman & Eagle
- 4. Gilt Bar
- 5. Scofflaw
- 6. The VIG
- 7. Vol. 39
- 8. Elephant & Castle
- 9. Elephant & Castle
- 10. Brando's Speakeasy
- 11. Broken Shaker at Freehand Chicago
- 12. Marge's Still
- 13. The Berkshire Room
- 14. Vintage Bar
- 15. Old Time Tap
- 16. Old Fashioned Meat Co Inc

- Monday: 6 AM–6 PM
- Tuesday: 6 AM–6 PM
- Wednesday: 6 AM–6 PM
- Thursday: 6 AM–6 PM
- Friday: 6 AM–6 PM
- Saturday: 6 AM–6 PM
- Sunday: Closed
1. Old Fashioned Donuts
Information and Reviews
Here are some key points from customer reviews:
- The vanilla frosting is incredibly sweet, while the apple fritter is absolutely amazing.
- The Pecan Apple Fritter is described as addictive and divine.
- Customers appreciate the classic glaze donut and massive apple fritters, highlighting the owner's longstanding presence.
- Visitors praise the delicious treats and friendly atmosphere, making it a must-visit spot for mouth-watering donuts.
Old Fashioned Donuts is a beloved establishment with a 4.7-star rating, attracting customers with its traditional charm and delectable offerings. Don't miss out on the opportunity to indulge in their delightful donuts and experience a true taste of nostalgia.

- Monday: 4 PM–12 AM
- Tuesday: 4 PM–12 AM
- Wednesday: 4 PM–12 AM
- Thursday: 4 PM–1 AM
- Friday: 4 PM–1 AM
- Saturday: 2 PM–1 AM
- Sunday: 4 PM–12 AM
2. Three Dots and a Dash
Information and Reviews
The business provides a wide range of offerings, including alcohol, beer, cocktails, food, happy-hour drinks, spirits, and wine. Customers can enjoy seating with the option to make reservations and experience exceptional payments service with credit and debit cards accepted. Parking is available in paid multi-storey car parks and street parking.
Customers have left positive reviews, highlighting the bar's outstanding features:
- Large tiki spot with great cocktails
- Extremely knowledgeable staff about cocktails
- Great vibe and Hawaii-like experience
- Exceptional service with strong, delicious, and balanced drinks

3. Longman & Eagle
Information and Reviews
The restaurant is popular for its breakfast, lunch, and dinner options, making it suitable for any time of the day. Customers have praised the fast service and the cozy atmosphere, highlighting the great coffee and desserts available on the menu.
Here are some key points from customer reviews:
- Varied menu options for breakfast, lunch, and dinner.
- Excellent service and cozy atmosphere.
- Great coffee and desserts available.
Visit Longman & Eagle to enjoy a delightful dining experience with friends and family, where you can savor the delicious offerings and unwind in a trendy yet casual setting.

- Monday: 4–10:30 PM
- Tuesday: 4–10:30 PM
- Wednesday: 4–10:30 PM
- Thursday: 4–10:30 PM
- Friday: 4–11 PM
- Saturday: 4–11 PM
- Sunday: 4–10:30 PM
4. Gilt Bar
Information and Reviews
- Customers rave about the attentive and friendly service provided by the staff.
- The truffle mozzarella sticks and roasted bone marrow appetizers are highly recommended for their amazing flavors.
- The main courses, including mussels, chicken, spicy pasta, and truffle bucatini, are praised for their freshness and taste.
- The overall dining experience at Gilt Bar receives high praise, making it a must-visit spot for both locals and tourists.
- Monday: 5 PM–1 AM
- Tuesday: 5 PM–1 AM
- Wednesday: 5 PM–1 AM
- Thursday: 5 PM–1 AM
- Friday: 5 PM–2 AM
- Saturday: 11 AM–2 AM
- Sunday: 11 AM–1 AM
5. Scofflaw
Information and Reviews
Some key points from customer reviews are:
- A nice Oasis to stop for a bite and a drink; features various gin varieties.
- Highly recommended for best cocktails ever, strange vibe but feels safe and comfortable.
- Scary fast food service but quality is not compromised; more than traditional bar food.
- Outstanding atmosphere for a dinner date; exquisite food and exceptional service.

- Monday: 5 PM–12 AM
- Tuesday: 5 PM–12 AM
- Wednesday: 5 PM–12 AM
- Thursday: 4 PM–2 AM
- Friday: 11:30 AM–2 AM
- Saturday: 10 AM–3 AM
- Sunday: 10 AM–12 AM
6. The VIG
Information and Reviews
- Beautiful space with great vibes
- Delicious spread board for dinner
- Perfect location before a show
- Great St. Patrick's Day drink specials
- Delicious flight of spreads
- Friendly and attentive service
- Tasty food and drinks
- Favorite item: turkey burger
- Good ambience for conversations
- Great service and excellent food
- Delicious dishes
- Highly recommended by customers

- Monday: 4–10 PM
- Tuesday: 4–10 PM
- Wednesday: 4–10 PM
- Thursday: 4–10 PM
- Friday: 4–11 PM
- Saturday: 4–11 PM
- Sunday: Closed
7. Vol. 39
Information and Reviews
Customer reviews rave about Vol. 39's inviting atmosphere, professional and knowledgeable staff, and beautifully crafted cocktails. Some key points from their reviews include:
- Opportunity to enjoy craft cocktails in a chill vibe without a crowd
- Perfect place to relax and cap off a night in Chicago
- Highly recommend trying the shrimp cocktail, dirty martini, and the "25 to life" spicy drink
- Great spot for unique and refreshing drinks and a prime location within the financial district
With a rating of 4.7 based on 306 reviews, Vol. 39 Lounge stands out as a top choice for those looking for a cozy yet upscale lounge experience in the heart of Chicago.

- Monday: 11 AM–1 AM
- Tuesday: 11 AM–1 AM
- Wednesday: 11 AM–1 AM
- Thursday: 11 AM–1 AM
- Friday: 11 AM–2 AM
- Saturday: 9 AM–2 AM
- Sunday: 9 AM–1 AM
8. Elephant & Castle
Information and Reviews
- Customers rave about the great beer selection
- Fast and friendly service is a standout feature
- The diverse cocktail menu is impressive
- Many appreciate the cozy atmosphere
Visit Elephant & Castle for a delightful dining experience.

- Monday: 7 AM–2 AM
- Tuesday: 7 AM–2 AM
- Wednesday: 7 AM–2 AM
- Thursday: 7 AM–2 AM
- Friday: 7 AM–2 AM
- Saturday: 7 AM–2 AM
- Sunday: 7 AM–2 AM
9. Elephant & Castle
Information and Reviews
The restaurant prides itself on providing an accessible environment with wheelchair-accessible entrance, seating, and toilet facilities. Offering a variety of beverages such as Alcohol, Beer, Cocktails, and Wine, patrons can enjoy a diverse selection of drinks. Moreover, the Restaurant has a range of dining options available, including Breakfast, Brunch, Lunch, Dinner, and Dessert, ensuring there is something for every craving.
Customers have left glowing reviews about Elephant & Castle. Here are some key points summarizing their experiences:
- This is hands down the best bar in Chicago with delicious food and outstanding drinks. The warm bartenders and staff make customers feel right at home.
- Delicious pub food with great vegetarian options like Cheesy Leek and Potato Pie and Bread Pudding.
- Although some dishes were disappointing, dessert was delicious, and the beer selection was pretty good.
- Customers rave about the fresh chicken pot pie, brussel sprouts, and tasty fried pickles and sausages wrapped in a pastry puff.
Visit Elephant & Castle today for a memorable dining experience that caters to all tastes and preferences.

- Monday: 5 PM–2 AM
- Tuesday: 5 PM–2 AM
- Wednesday: 5 PM–2 AM
- Thursday: 5 PM–2 AM
- Friday: 5 PM–2 AM
- Saturday: 5 PM–3 AM
- Sunday: 5 PM–2 AM
10. Brando's Speakeasy
Information and Reviews
This hidden gem not only features karaoke nights but also live music performances and quiz nights, providing an entertaining experience for all. Customers have praised the ambience of Brando's Speakeasy, with one guest mentioning it as a fun spot for a night out with friends. Another visitor commended the extensive song selection available through the bar's app, ensuring a diverse karaoke experience.
Overall, reviews highlight the lively atmosphere of Brando's and the quality of its offerings, making it a must-visit destination for those looking for a good time in Chicago.
- Ambience described as fun and entertaining with a great song selection
- Lively atmosphere perfect for a night out with friends
- Extensive drink menu with great beers and cocktails

- Monday: 4 PM–1 AM
- Tuesday: 4 PM–1 AM
- Wednesday: 4 PM–1 AM
- Thursday: 4 PM–1 AM
- Friday: 4 PM–2 AM
- Saturday: 4 PM–2 AM
- Sunday: 6 PM–12 AM
11. Broken Shaker at Freehand Chicago
Information and Reviews
- The atmosphere is described as casual, cozy, trendy, and upmarket, catering to a diverse crowd.
- The bar is known for its great cocktails, fast service, live music, and live performances, adding to the overall experience.
- Some customers have praised the friendly bartenders, the cozy lounge area, and the unique cocktails offered.
Overall, Broken Shaker at Freehand Chicago provides a lively and enjoyable setting for guests to relax and unwind.

- Monday: Closed
- Tuesday: 4:30 PM–12 AM
- Wednesday: 4:30 PM–12 AM
- Thursday: 4:30 PM–12 AM
- Friday: 4:30 PM–12 AM
- Saturday: 4 PM–1 AM
- Sunday: Closed
12. Marge's Still
Information and Reviews
Some customers have shared their positive experiences:
- Family-friendly environment with a great local vibe
- Delicious, massive chicken pot pie and friendly staff
- Excellent neighborhood tavern with a superb beer selection and unique dishes like Chicken Pot Pie
- Cozy atmosphere with accommodating staff and delicious food and drinks
Reviews mention dishes like burgers, fries, and desserts, all prepared with care. The friendly and attentive staff contribute to the overall welcoming ambiance of Marge's Still. So whether you're looking for a quiet weekday dinner or a place to catch the game with friends, this restaurant has something for everyone.

- Monday: 5 PM–12 AM
- Tuesday: 5 PM–12 AM
- Wednesday: 5 PM–12 AM
- Thursday: 5 PM–12 AM
- Friday: 5 PM–2 AM
- Saturday: 4 PM–2 AM
- Sunday: 5 PM–12 AM
13. The Berkshire Room
Information and Reviews
With a total of 418 reviews and an impressive rating of 4.4, customers have left positive feedback about The Berkshire Room. Some key points from the reviews:
- This hidden gem offers an intimate setting with great service and premium drinks.
- The cocktails are well balanced, and customers can stay for hours enjoying the ambiance.
- The atmosphere is cozy and the cocktails are expertly crafted, making each sip a delight.
- Customers appreciate the attentive bartenders and the delicious drinks on the menu.

- Monday: 11 AM–2 AM
- Tuesday: 11 AM–2 AM
- Wednesday: 11 AM–2 AM
- Thursday: 11 AM–2 AM
- Friday: 11 AM–2 AM
- Saturday: 11 AM–3 AM
- Sunday: 11 AM–2 AM
14. Vintage Bar
Information and Reviews
The establishment is committed to accessibility, with wheelchair-accessible entrances and toilets available. In terms of offerings, Vintage Bar provides a wide selection of alcohol, beer, cocktails, dancing, food, happy-hour drinks, happy-hour food, spirits, and wine. The dining options include comfortable seating arrangements, and essential amenities like restrooms are readily accessible to patrons.
The atmosphere of Vintage Bar is described as casual, cozy, and trendy, catering to diverse crowds including groups. The bar is open to planning events and accepts reservations. Accepted payments include credit cards and debit cards, although credit card payment availability may be subject to change. Convenient parking options, including free street parking, are available for customers.
Customer reviews highlight the positive aspects of Vintage Bar, with notable features such as a lively atmosphere on Wednesday nights, great drinks, and standard food offerings. Despite some feedback on slow service and occasional mishaps with happy hour pricing, patrons appreciate the lively ambiance, delicious food, and friendly staff. The inclusive and fun vibe of the bar attracts various visitors, from salsa dance enthusiasts to those seeking a relaxed night out with friends.

- Monday: 11 AM–2 AM
- Tuesday: 11 AM–2 AM
- Wednesday: 11 AM–2 AM
- Thursday: 11 AM–2 AM
- Friday: 11 AM–2 AM
- Saturday: 11 AM–3 AM
- Sunday: 11 AM–2 AM
15. Old Time Tap
Information and Reviews
Some key points from customer reviews include:
- Great atmosphere and people
- Reasonably priced and goes above and beyond
- Large space, great service, and super friendly staff
- Needs some updating but has the potential to be a prime location
The business offers a variety of alcohol options, bar games, fast service, great beer selection, and quiz night. Customers can enjoy a casual and cozy atmosphere with amenities such as toilets and Wi-Fi. Additionally, they accept credit cards, debit cards, and NFC mobile payments. With free street parking and a parking lot, patrons can easily access this fantastic bar for a night of fun and relaxation.

- Monday: 5:30 AM–5 PM
- Tuesday: 5:30 AM–5 PM
- Wednesday: 5:30 AM–5 PM
- Thursday: 5:30 AM–5 PM
- Friday: 5:30 AM–5 PM
- Saturday: Closed
- Sunday: Closed
16. Old Fashioned Meat Co Inc
Information and Reviews
- Customers commend the employees for their exceptional service.
- The location is not very truck-friendly, according to one review.
- Visitors praise the cleanliness and strict safety protocols for Covid.
- The corned beef is highly recommended and considered the best by many.
With delivery as one of their service options, Old Fashioned Meat Co Inc goes above and beyond to meet and exceed their customers' needs. Visit their website to explore their products and place your order today!
Map of Old-Fashioned Chicago Bars
Discover the charm and history of old fashioned Chicago with this detailed map showcasing iconic landmarks, historic neighborhoods, and timeless attractions. From the bustling streets of downtown to the cozy corners of the suburbs, this map will guide you through a journey back in time to the classic beauty of the Windy City.

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