Best of 20 cocktail bar in Logan Square
Welcome to the vibrant world of cocktail bars in Logan Square. This Chicago neighborhood is known for its thriving culinary and nightlife scene, and its cocktail bars are no exception. From speakeasy-style dens to trendy rooftop lounges, the cocktail bar scene in Logan Square is a must-visit for any cocktail connoisseur. Experience innovative concoctions and classic drinks, all served with a unique Logan Square twist. Come and explore the best cocktail bar destinations in Logan Square.
- 1. Billy Sunday
- 2. Spilt Milk
- 3. The Meadowlark
- 4. Scofflaw
- 5. The Walk In
- 6. Penumbra
- 7. Best Intentions
- 8. Longman & Eagle
- 9. The Welcome Back Lounge
- 10. Weegee's Lounge in Logan Square
- 11. Estereo in Logan Square
- 12. The Pink Squirrel
- 13. The Whistler
- 14. The Native
- 15. Green Eye Lounge
- 16. The Heavy Feather
- 17. Slippery Slope
- 18. Outside Voices
- 19. Easy Does It in Logan Square
- 20. Off Site Bar
1. Billy Sunday
Prohibition-era inspired cocktails and extensive drinks menu

Billy Sunday is a charming restaurant known for its unique atmosphere, great music, and innovative cocktails. The staff is friendly and knowledgeable, making it a popular spot for a fun night out. When visiting with a group, you can sample a variety of their creative drinks, including the popular Tea Time and Papa Don't Peach.
What sets Billy Sunday apart is their presentation – the drinks are served in unique vessels that add to the overall experience. If you appreciate craft cocktails, Billy Sunday is a must-visit. With its appealing atmosphere, excellent service, and standout cocktails, it promises a memorable experience for anyone looking for a fun night out.
TOPICS
- Social Gatherings
- American Cuisine
- Cheap Eats
- Downtown Spots
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2. Spilt Milk
Comfort food, late-night menu

Spilt Milk is a popular spot in Logan Square known for its delicious and unique cocktails. Many customers rave about the quality and taste of the drinks, making it a top destination for those looking for a fancy and enjoyable drinking experience.
If you're searching for the perfect place in Logan Square with an impressive selection of drinks, Spilt Milk is the spot for you. From their raved-about cocktails to their unique and tasty offerings, this joint is a must-visit for anyone looking to indulge in some delightful beverages.
TOPICS
- American Cuisine
- Mid-Range
- Downtown Spots
- Dinner
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3. The Meadowlark
Live music, handcrafted cocktails, and farm-to-table menu

Located in Logan Square, Meadowlark is a hidden bar that offers a clubhouse-like atmosphere for its patrons. The nondescript entrance, located on a quiet side street, and the subtle signage, featuring only a bird silhouette, make it easy to miss. However, inside, guests are treated to a dark wooden interior, cozy leather couches, and a selection of small plates and drinks. It is a popular spot for drinks, and guests are advised to arrive early to secure a table or a seat at the bar. Reservations are available for parties of four or more.
The drink menu at Meadowlark is varied and changes frequently, with the option to purchase a copy of the menu as a souvenir. The bar has a speakeasy-like atmosphere, adding to its exclusivity and allure. It is recommended to secure a reservation if you plan to visit with a group of four or more people. The intimate setting, unique ambiance, and quality offerings make Meadowlark a must-visit spot for anyone looking for a memorable drinking experience.
TOPICS
- Social Gatherings
- American Cuisine
- Downtown Spots
- Late Night
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4. Scofflaw
Extensive liquor selection and unique decor

The establishment offers a great selection of cocktails, with the featured cocktail being a particularly good choice. In addition to their cocktails, they also have a strong beer list, which includes several draft offerings. The service was commendable, given that it was an opening night. The staff were attentive, helpful, and efficient, ensuring that guests had a positive experience.
All of the craft cocktails at this establishment are excellent, highlighting the bar's mixology skills. Whether you're a fan of classic cocktails or looking to try something new, the bar has something to offer. The beer list is also impressive, with a variety of options to choose from. Overall, the bar offers a great selection of drinks and impressive service, making it a worthy destination for cocktail and beer enthusiasts.
TOPICS
- American Cuisine
- Vegetarian Options
- Mid-Range
- Downtown Spots
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5. The Walk In
Handcrafted Italian cuisine and a lively atmosphere

The atmosphere at the venue is lively and upbeat, with the music selection featuring popular hits from the 90s and classic hip hop tracks. This creates a positive and entertaining environment for customers. Bartenders play a crucial role in maintaining this atmosphere by serving drinks efficiently and effectively.
The quality of the drinks at this establishment is highly notable, as they are carefully mixed with quality ingredients. The bartenders are skilled professionals who take pride in their work, ensuring that each drink is made to perfection. Their friendly and approachable demeanor further enhances the overall experience, making customers feel welcome and valued.
TOPICS
- Social Gatherings
- Happy Hours
- Fusion Cuisine
- Hidden Gems
6. Penumbra
Live music performances and art exhibits

The food establishment offered delicious food and exciting cocktails that left a memorable experience. However, there was a slight issue with the order tracking which was quickly resolved. The management went above and beyond to make up for the inconvenience, providing extra items. This gesture demonstrated excellent customer service and a genuine desire to ensure customer satisfaction.
Aside from the delectable food and impressive drink menu, the venue also hosts live music. It's an excellent spot to enjoy a few drinks while listening to talented musicians. The cocktails are unique and add to the overall entertainment of the venue. Whether looking for a place to grab a drink or see some live music, this establishment is a great choice.
TOPICS
- American Cuisine
- Mid-Range
- Downtown Spots
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7. Best Intentions
Live Music, Craft Cocktails, and Comfort Food

The establishment offers unique and competitively priced drinks, making it an attractive option for those looking for something out of the ordinary without breaking the bank. The knowledgeable and friendly bartenders are happy to guide customers through the menu, ensuring a great experience for all.
Despite its fancy exterior, the bar has a hidden dive-bar vibe. The patio is a particular highlight, providing a great space to enjoy the bar's amazing drinks and relax in a casual atmosphere. The staff's great attitude and attentive service add to the overall positive experience, making it a must-visit destination for cocktail lovers.
TOPICS
- Social Gatherings
- Happy Hours
- Downtown Spots
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8. Longman & Eagle
Inn rooms, Michelin-starred restaurant, and lively bar

The cocktail bar at Longman & Eagle is a must-visit destination for any cocktail lover. The knowledgeable bartenders are experts in their craft, skillfully creating an impressive range of drinks that are sure to impress. Whether you're a seasoned cocktail enthusiast or new to the scene, you're sure to find something to love on their menu. The ambiance of the bar is cozy and inviting, making it the perfect spot to unwind after a long day or to kick off a night out with friends.
Nestled within Longman & Eagle, the cocktail bar is a hidden gem that shouldn't be missed. The dim lighting and intimate atmosphere make it an ideal location for a romantic evening or a night of quality time with friends. The cocktails themselves are expertly crafted, featuring unique and unexpected flavor combinations that are sure to excite even the most discerning palates. From classic recipes to innovative new creations, the cocktail bar at Longman & Eagle is a true standout in the world of mixology.
TOPICS
- Social Gatherings
- American Cuisine
- Mid-Range
- Downtown Spots
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9. The Welcome Back Lounge
Intimate live music venue, extensive beer selection, delicious pub food

The bar provides a wide selection of enjoyable and tasty drinks. The bartenders are known for their friendliness and efficiency, ensuring quick and pleasant service. Recently, an event was held at this venue, and the experience was overwhelmingly positive. The food stood out for its fun and delicious qualities, making it an ideal choice for social gatherings.
During a recent event, the bar's casual atmosphere and enjoyable food contributed to a successful occasion. The upbeat and delightful food options were a perfect fit for the party's atmosphere. The bar's reputation for friendly and competent bartenders, combined with its diverse drink menu and enjoyable food, makes it a great location for social gatherings.
TOPICS
- Social Gatherings
- Vegetarian Options
- Happy Hours
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10. Weegee's Lounge in Logan Square
Two stories tall, speakeasy vibes, secret backroom

Weegee's Lounge is a retro cocktail bar located in the underdeveloped area of west Logan Square. The owner of the lounge is known for their hospitality, creating a nice atmosphere with a good vibe. The establishment offers a great selection of 'craft' beers and a menu featuring old-timey cocktails. The bar is so appealing that the author plans to visit again.
Stepping into Weegee's Lounge is like stepping back in time. The bar fits perfectly into the third category of a checklist, although the first two are not specified. The vintage decor and old-fashioned cocktails on the menu contribute to the time-warp experience. Weegee's is a hidden gem in an underdeveloped area, providing a unique and enjoyable escape from the present.
TOPICS
- Social Gatherings
- American Cuisine
- Affordable Nightlife
- Hidden Gems
11. Estereo in Logan Square
Authentic Cuban cuisine, lively atmosphere, live music

The cocktail menu at this establishment includes a variety of drinks based on spirits from Latin America. One example is the Breezy, which is the house cocktail and features a unique combination of yerba mate, falernum, lime, and the spirit of your choice. Carbonation is used to give the Breezy a refreshing and bubbly quality.
The drinks at this place are not only delicious, but they also showcase some lesser-known spirits. Two examples are Cachaça, a spirit from Brazil, and pisco, a grape brandy from Peru and Chile. These ingredients add depth and flavor to the cocktails, making them stand out from typical drink options.
TOPICS
- Celebrations
- Italian Cuisine
- Vegetarian Options
- Mid-Range
12. The Pink Squirrel
Unique 1950s-inspired decor and atmosphere

This Logan Square establishment offers a unique experience with its combination of creative drinks, vintage atmosphere, and entertainment options. The main attractions include mini bowling and milkshakes, both of which can be enjoyed in a setting that features retro decor.
If you're looking for a fun and distinctive night out, this spot is definitely worth checking out. In addition to mini bowling and milkshakes, they also serve classic cocktails and offer a selection of creative drinks. The vintage decor adds to the overall experience, making it a great place to relax and have a good time. I highly recommend giving it a try!
TOPICS
- Social Gatherings
- American Cuisine
- Happy Hours
13. The Whistler
Welcoming atmosphere, quality comfort food, celebrating local talent

The Whistler is a notable new establishment in Chicago's Logan Square neighborhood, offering a well-curated selection of drinks in a cozy and inviting atmosphere. The bar is known for its carefully crafted cocktails, which are sure to delight and satisfy visitors. Whether you're a local looking for a new favorite watering hole or a tourist exploring the city's vibrant bar scene, The Whistler is definitely worth a visit.
In addition to its top-notch drinks, The Whistler also boasts a lively and enjoyable ambiance. The indoor space is intimate and perfect for a night of conversation and dancing, while the outdoor area provides a more relaxed setting for socializing. No matter where you choose to spend your time, you can count on the staff to be friendly and attentive, ensuring that your visit is both enjoyable and memorable. Whether you're looking for a casual night out or a place to celebrate a special occasion, The Whistler is the perfect spot.
TOPICS
- Social Gatherings
- Asian Cuisine
- Dinner
- Late Night
14. The Native
Stylish interior, delicious food, and lively atmosphere

The drink selection at this establishment is varied, affordable, and of high quality. Cocktails, beer, and frozen drinks made with non-dairy milk are among the offerings. This makes it a great place for people with dietary restrictions.
The atmosphere is welcoming and lively, with friendly and attentive staff. The patio area is particularly pleasant, providing a great space to relax. It's a perfect spot for those looking to finish up work or studies, as they offer free WiFi. The combination of the enjoyable ambiance and the top-notch service makes for an ideal location to unwind with a drink after a long day.
TOPICS
- Social Gatherings
- Happy Hours
- Hidden Gems
15. Green Eye Lounge
Cozy patio, extensive cocktail menu

This bar has a relaxed and enjoyable atmosphere, with a $10 minimum spend that is typical for this kind of establishment. The only food option available is an expensive bag of chips. However, the bar offers a variety of card games and pinball machines for entertainment. It is a great classic Chicago bar, located right by the blue line, with a nostalgic decor.
The drink menu at this bar is uncomplicated and easy to navigate. While cash is the preferred method of payment, using cards will still be accepted but with a 10% surcharge. The interior is spacious, providing enough room for large groups to gather comfortably. Overall, it is a great place to socialize, with entertainment options and a convenient location in Chicago.
TOPICS
- Hidden Gems
- Affordable Nightlife
16. The Heavy Feather
Unique craft cocktails, intimate setting

The Heavy Feather is a relaxed, retro-themed lounge located above the dance bar staple Slippery Slope in Logan Square. Although it features a disco ball, the atmosphere is more subdued, making it an ideal spot for a casual hang. However, some patrons may find it frustrating that if they grow tired of the relaxed vibe, they have to go down to Slippery Slope's dancefloor to experience a more upbeat atmosphere.
The Heavy Feather is a distinct bar above Slippery Slope, which can be inconvenient for those who want a change of pace since they have to move to a different venue to experience a dancefloor and a more energetic ambiance. Despite this, the bar has a classy and upscale feel, while Slippery Slope has more of a dive bar vibe. Fortunately, the bartenders are skilled and attentive, providing great service to patrons.
TOPICS
- Corporate Events
- American Cuisine
- High-End
- Downtown Spots
17. Slippery Slope
Spacious patio, unique decor, weekend brunch

The space where the event is being held features cute décor and string lights, creating a cozy and inviting atmosphere. As the main event comes to a close, there's a photo booth available in the back of the space. This booth allows attendees to capture and preserve memories from the night, ensuring that the good times don't have to end when the event is over.
The event's location has a charming ambiance, thanks to the adorable decorations and twinkling string lights. As the main portion of the event draws to a close, guests can make their way to the back of the space to find a photo booth. This added touch is a fun way for attendees to remember the evening, as they can take home physical photos of the memories they made at the event.
TOPICS
- Social Gatherings
- American Cuisine
- Affordable Nightlife
- Downtown Spots
18. Outside Voices
Serving authentic Mediterranean dishes with creative twists

Outside Voices is a welcoming establishment with a cozy indoor space, ideal for a relaxed evening. It features a remarkable cocktail bar where guests can enjoy top-notch drinks. The knowledgeable bartenders are friendly and contribute to the establishment's warm atmosphere.
The cocktail bar at Outside Voices is a standout, offering a variety of delicious concoctions. Among the most recommended options are the signature cocktails, which are both innovative and expertly crafted. The staff's expertise and attention to detail ensure that each drink is perfect, making for a memorable experience.
TOPICS
- Mediterranean Cuisine
- Downtown Spots
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19. Easy Does It in Logan Square
Community-oriented atmosphere with local events

The atmosphere at this establishment is laid back and friendly, making it a great place to relax and enjoy a drink. The cocktails served here are a highlight, with a wide variety of options to choose from. The staff is super friendly and adds to the overall welcoming and pleasant ambiance.
This is a wine bar, but it has a lounge-like feel that sets it apart from other wine bars. It is sophisticated and chic, but it does not have the club-like vibes that some wine bars can have. Despite its more laid-back atmosphere, it is still possible to dance here if the mood strikes. Overall, it is a very cute and inviting spot to enjoy a glass of wine.
TOPICS
- Social Gatherings
- Affordable Nightlife
- Downtown Spots
- Late Night
20. Off Site Bar

TOPICS
- Affordable Nightlife
- American Cuisine
- Downtown Spots