Best of 20 bars in Chicago
Chicago is a vibrant city known for its diverse and exciting nightlife. Among the many options, bars in Chicago are a popular choice for both locals and tourists. These establishments range from sleek rooftop bars with stunning city views to cozy neighborhood taverns filled with charm. Whether you're looking for a place to watch the game, enjoy live music, or sip on craft cocktails, Chicago's bar scene has something for everyone. So, if you're planning a night out in the Windy City, be sure to check out its bustling bars in Chicago.
- 1. Delilah's
- 2. The Green Door Tavern
- 3. Old Town Ale House
- 4. Matchbox Bar
- 5. 2Twenty2 Tavern
- 6. Rossi's
- 7. Theory
- 8. Long Room Chicago
- 9. Richard's Bar
- 10. Broken Shaker at Freehand Chicago
- 11. The Milk Room
- 12. Three Dots and a Dash
- 13. Brando's Speakeasy
- 14. Bar Louie - Printers Row
- 15. The Boss Bar
- 16. Streeter's Tavern
- 17. Kasey's Tavern
- 18. Vol. 39
- 19. Best Intentions
- 20. Shamrock Club
1. Delilah's
Live music, extensive liquor selection

Delilah's is a popular bar, particularly for punk acts touring through Chicago. It boasts a rotating selection of beers, featuring well-known choices such as Half-Acre Daisy Cutter, Goose Island Sophie, and New Belgium La Folie. The bar has gained a reputation as a post-show watering hole for rock and punk musicians.
The interior of Delilah's is narrow and cozy, making it a lively and friendly environment. Patrons should be prepared to socialize and interact with those around them, given the tight quarters. Watching a game of pool can be an amusing experience, given the cramped space. Despite the crowded conditions, Delilah's maintains a welcoming and enjoyable atmosphere.
TOPICS
- Social Gatherings
- Corporate Events
- American Cuisine
- Downtown Spots
2. The Green Door Tavern
Chicago's oldest tavern, historic atmosphere, craft beers

The Tavern, known as the "oldest bar in Chicago," successfully creates an authentic atmosphere with its decor and historic theme. The owners have taken great care to preserve the establishment's history, making it a fascinating place to visit. Downstairs, there is even a speakeasy, which adds to the lively atmosphere and provides excellent drinks.
This historic tavern offers a unique experience with its vintage decor and speakeasy, which transports patrons to a different time. The bar is well-known for its impressive history and the care taken to maintain its antique charm. With an extensive drink menu, the Tavern is the perfect spot for anyone looking to step back in time and enjoy a delicious beverage in a one-of-a-kind atmosphere.
TOPICS
- Social Gatherings
- American Cuisine
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3. Old Town Ale House
Cash-only, no food served after 10pm

Old Town Ale House is one of the best dive bars I have visited, standing out for its authenticity and unique atmosphere. It is remarkably free of pretension or gimmicks, with a strict no-nonsense policy that ensures a pleasant experience for all patrons. The bar is known for its diverse and interesting clientele, as well as its great selection of brews and spirits. The jukebox at Old Town Ale House is also a highlight, featuring a wide variety of eclectic tunes that add to its charm.
As a true dive bar, Old Town Ale House offers a dimly lit and slightly musty atmosphere, complete with fascinating bathroom graffiti that is unfortunately repainted over frequently. The bar does not serve any fancy or overly-complicated drinks, instead focusing on stiff cocktails that are sure to please. With late-night hours and a book swap available, the bar has a laid-back and welcoming vibe that encourages patrons to stay awhile and soak it all in. The jukebox, with its kickass selection of music, is the cherry on top of a truly unforgettable dive bar experience.
TOPICS
- Social Gatherings
- Happy Hours
- Downtown Spots
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4. Matchbox Bar
Hidden speakeasy-style bar, unique craft cocktails

This small yet impressive establishment has been a favorite of mine for numerous years. The bartenders are skilled and experienced, providing excellent service (I have been drinking for many years and know what good service is). The bar area is intimate and cozy, but if you can't get a spot there, fear not. There are also heated outside options that are quite nice.
This spot is perfect for a romantic evening. I recommend bringing your favorite date and cozying up inside the bar. The staff is welcoming and talented in their craft, making the experience even more enjoyable. Whether you're looking for a place to grab drinks with friends or a spot for a romantic night out, this establishment is a great choice.
TOPICS
- Social Gatherings
- American Cuisine
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5. 2Twenty2 Tavern
Extensive wine list, creative cocktails, and knowledgeable staff

The food at this establishment is delicious and satisfying. The jalapeño ranch sauce, in particular, is a favorite among guests. Everyone seems to enjoy the taste and appreciates its unique flavor.
In addition to the food, the drinks are also a highlight. The bar offers a wide variety of beers on tap, as well as specialty drinks that are carefully crafted. Guests have consistently positive things to say about the quality of the drinks, which are made with care and attention to detail.
TOPICS
- Holiday Celebrations
- Mediterranean Cuisine
- Happy Hours
6. Rossi's
Hand-tossed pizzas, house-made pasta, and an extensive wine list

The establishment in question is a classic dive bar, boasting a dimly lit interior covered in posters and stickers. The atmosphere is warm and welcoming, characterized by friendly patrons and an excellent bartender. This dive bar is a small, cozy pub, perfect for those looking to escape the tourist-filled areas and enjoy a few drinks in a more relaxed setting.
The staff at this establishment are particularly noteworthy, with the bartenders and doorman receiving high praise for their cool and approachable demeanor. The doorman, in particular, is described as a true gentleman. Overall, this dive bar is a great spot for anyone seeking a no-nonsense, authentic drinking experience.
TOPICS
- Mid-Range
- Hidden Gems
- Vegan Options
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7. Theory
Seasonal outdoor patio, craft cocktails, weekend brunch

Watching sports with friends is highly enjoyable at this bar, which boasts a spacious bar area and numerous screens to catch every critical moment of the game. The venue exudes a fantastic vibe, particularly during game nights, when the energy is at its peak.
Friendly bartenders serve excellent drinks at this bar, enhancing the overall positive atmosphere. The quality of the drinks is top-notch, making it an excellent spot to enjoy a drink while watching sports.
TOPICS
- Social Gatherings
- American Cuisine
- Downtown Spots
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8. Long Room Chicago
Game room with pool tables and vintage arcade games

The bar comes to life at night with a wide selection of beers, whiskeys, and cocktails, providing a sparkling and vibrant atmosphere. The staff is friendly and attentive, contributing to the welcoming and enjoyable ambiance.
This bar is truly exceptional, known for its top-notch staff, delicious cocktails, and ever-changing menu. The space is ideal for a social night out with friends, complete with great conversation and excellent drinks.
TOPICS
- American Cuisine
- Budget-Friendly Eats
- Downtown Spots
- Breakfast
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9. Richard's Bar
Historic location, no-frills atmosphere

If you're looking for a cheap drink, this place is worth checking out. However, be forewarned that smoking is allowed on the premises, which may not be ideal for everyone. The drinks are a highlight of this establishment, with customers praising their affordability.
Despite the budget-friendly prices, the drink quality is not compromised. The bar offers a range of options, appealing to a variety of tastes. However, the prevalence of smoking and the lack of a non-smoking section may be a deterrent for some. Overall, the drinks are the main attraction of this establishment, making it a good choice for those looking for a cheap and casual drinking experience.
TOPICS
- American Cuisine
- Downtown Spots
- Late Night
- Seasonal Times
10. Broken Shaker at Freehand Chicago
Handcrafted cocktails, whimsical atmosphere, rooftop view

The bar in question is a popular spot in Chicago, known for its innovative and delicious cocktails. The menu features a variety of unique concoctions, but if nothing strikes your fancy, the skilled bartenders can whip up something special just for you. They are highly experienced and can create any drink you can imagine.
Sabrina, one of the bartenders, is particularly noteworthy. She created a new favorite cocktail for the author and their friends, expertly balancing the flavors to suit their tastes. On top of her impressive mixology skills, Sabrina was described as very kind and friendly, making the bar experience even more enjoyable. The cozy and charming atmosphere of the bar and lounge, combined with the exceptional service, make it a must-visit destination in Chicago.
TOPICS
- American Cuisine
- Social Gatherings
- Late Night
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11. The Milk Room
Historic location, unique concept

The Milk Room in the Chicago Athletic Association Hotel is a must-visit prohibition-era whiskey bar, curated by one of the city's top mixologists. This speakeasy-style bar offers a unique and intimate experience, with a capacity of only eight people, requiring reservations in advance. The atmosphere is dimly lit and exudes a dark and seductive vibe, with a focus on rare spirits and specialty cocktails.
The Milk Room's small size adds to its exclusivity, making it a cozy and historic spot for patrons. While the food offerings are on the pricier side, dishes like steak tartare are not to be missed. The bartender is highly knowledgeable and affable, contributing to the exceptional service provided. Despite the expensive drinks and food, the experience is well worth it for the intimate and unique atmosphere, as well as the opportunity to try rare spirits and specialty cocktails.
TOPICS
- Celebrations
- American Cuisine
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12. Three Dots and a Dash
Extensive rum selection, tiki-themed decor, and craft cocktails

The food offered at the establishment is of good quality and possesses a unique flavor that sets it apart from other dining options. The atmosphere within the establishment contributes to a pleasant dining experience. The drink options are a highlight, with unique and interesting flavors that are sure to satisfy. The drinks are characterized by their vibrant colors and sweet tastes, making them a delightful addition to any meal.
The bartenders at the establishment are skilled professionals, able to create and mix drinks with expertise and efficiency. The drinks themselves are given quirky and creative names that add to their appeal. The combination of unique flavors, skilled bartenders, and fun names makes for an enjoyable drinking experience. Whether looking for a pre-dinner drink or a post-meal nightcap, the establishment's drink menu is sure to have something for everyone.
TOPICS
- Social Gatherings
- Fusion Cuisine
- Downtown Spots
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13. Brando's Speakeasy
Hidden Speakeasy Experience

Brando's Speakeasy was the destination due to its reputation as a Karaoke bar. Upon arrival, my group headed to the back bar area, which was mostly empty. We purchased a round of drinks while we waited for the Karaoke to begin.
The bar offered a great atmosphere, with excellent drinks and outstanding bartenders. Phil showcased a fantastic sense of humor, Melissa was incredibly kind, and Yoli added a touch of unpredictability that made our experience even better.
TOPICS
- Social Gatherings
- Downtown Spots
- Mid-Range
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14. Bar Louie - Printers Row
Spacious patio with city views

Bar Louie - Printers Row is a well-known establishment for its inviting atmosphere and top-notch service. The restaurant offers a popular brunch, featuring $3 mimosas that draw in guests looking for a great deal. In addition to the affordable drinks, Bar Louie is famous for its chef-inspired menu that features delicious food and signature cocktails.
The comfortable setting of Bar Louie - Printers Row makes it easy to relax and enjoy the atmosphere. The restaurant provides a space where guests can unwind and socialize while enjoying excellent food and drinks. With its combination of great service, affordable prices, and delicious offerings, Bar Louie - Printers Row is a popular destination for anyone looking for a great dining experience.
TOPICS
- American Cuisine
- Mid-Range
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15. The Boss Bar
Rooftop bar with panoramic city views

The cost of the low-priced drinks at this establishment is a gloomy and unkempt atmosphere. Some guests have reported slow service, but there are also those who have commended certain employees for their excellent service.
The drinks at this location are affordably priced, with none exceeding $10. However, the trade-off for the low cost is a dirty and unkempt environment. The service is described as average, but there are individual employees who have been praised for their good service.
TOPICS
- Dinner
- Late Night
- Downtown Spots
- Hidden Gems
16. Streeter's Tavern
Extensive beer selection and big-screen TVs

Streeter's Bar is an excellent choice for locals looking for a drink in the downtown area. It stands out from other bars, such as hotel bars that can be pretentious and themed bars that may come across as tacky. Streeter's has a welcoming neighborhood bar atmosphere that seems somewhat out of place in its current location, reminiscent of what the area may have been like in the past.
My friend and I stopped by Streeter's for an after-dinner drink, and we were glad we found the place. The dimly lit basement bar with pool tables, TVs, and a friendly atmosphere made for a great time. We sat at the bar, and our bartender, Douglas, was engaging and made for great conversation. Overall, Streeter's is a cool, neighborhood bar that I highly recommend.
TOPICS
- Social Gatherings
- Cheap Eats
- American Cuisine
- Late Night
17. Kasey's Tavern
Extensive beer list and large TVs for sports

Kasey's Tavern is a standout bar in Chicago, known for its relaxed and inclusive atmosphere. The ambiance is enjoyable and lively, making it an ideal place to hang out with friends or unwind after a long day. The bartenders at Kasey's Tavern are a highlight, noted for their friendly and approachable demeanor.
If you're a craft beer enthusiast, Kasey's Tavern is the place to be. They offer an excellent selection of local beers that are sure to satisfy any palate. Whether you're a beer connoisseur or just looking for a great spot to relax and enjoy a drink, Kasey's Tavern is the perfect destination. With its welcoming atmosphere, top-notch bartenders, and impressive beer list, it's no wonder why this Chicago bar is a local favorite.
TOPICS
- Social Gatherings
- American Cuisine
- Mid-Range
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18. Vol. 39
Historic location, famous for Chicago-style pizza

Vol. 39 is an excellent choice for a cocktail in the Loop, featuring a rotating menu with thoughtfully crafted drinks and unique themes. The establishment offers a speakeasy atmosphere, making it a great spot for an intimate date night, networking event, or a starting point for a pub crawl.
The cozy bar provides a comfortable environment, and the collection of wine, whiskey, and other craft spirits is impressive. Whether you're looking to enjoy a quiet evening or socialize with colleagues, Vol. 39 is the perfect place to start your night or enjoy a few drinks. With its convenient location and welcoming atmosphere, it's no wonder that Vol. 39 is a popular spot for locals and visitors alike.
TOPICS
- Corporate Events
- Celebrations
- American Cuisine
- Downtown Spots
19. Best Intentions
Committed to locally sourced, organic ingredients

The bartenders at this establishment are known for their friendly demeanor and extensive knowledge of the menu. They serve unique and competitively priced drinks that are sure to satisfy.
The food at this location is limited, but what they do have is full of flavor. The menu features tasty options with a spicy kick, such as chips & skins and a muffaletta sandwich. Whether you're looking for a drink or a bite to eat, this place has something for you.
TOPICS
- Social Gatherings
- Happy Hours
- Downtown Spots
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20. Shamrock Club
Extensive beer selection, rooftop bar, game area, live music

A casual, dingy bar is described as having cheap drinks and neon beer signs. The bar has a less-than-welcoming atmosphere due to offensive graffiti found in the bathroom. On a positive note, the bar serves as a classic neighborhood dive. The service is reportedly excellent and the lunch special of steak tacos is highly recommended.
In summary, while the physical appearance and some aspects of the bar may not be to everyone's liking, it offers a great dive bar experience. With excellent service and delicious steak tacos, it serves as a great spot for a casual lunch or drink.
TOPICS
- Social Gatherings
- Downtown Spots
- Happy Hours
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