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Cocktail spots in Near South Side

You expect your cocktails to be prepared with precision and care.

Based on 604 Opinions
+601
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Updated April 2026
01
Casa Tulum image 1
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Mexican restaurant

Mexican restaurant buzzes with live DJ and fire show creating an energetic vibe. Two bars with TVs serve rich cocktails like Blue Hawaiian in iced coconut shells. Guests enjoy great margaritas and flavorful dishes in a vibrant setting.

Rich and creamy cocktails come served in real iced coconut shells with coconut shavings on top. Drinks like the Blue Hawaiian and Coconut Tulum stand out for their excellent flavors.

People are saying

"The food here is amazing, fresh, and perfectly seasoned."

"The service here for Date Spots is attentive and above and beyond."

"You have to try the refreshing coconut cocktails."

Good to know

1

Happy hour starts at 3 PM.

2

Ask for the $10 margaritas special on Mondays and Tuesdays.

3

Street parking is easy to find and free on Sundays.

02
Buttercup image 1

Small, intimate space shifts from cozy cafe to swanky speakeasy bar with soft lighting and curated 1940s/50s decor. Cocktails offer a unique variety including standout Black Manhattan and non-alcoholic options. Atmosphere stays chill and welcoming, perfect for quiet dates or after-work drinks.

Cocktails here offer a unique and fun variety with plenty of non-alcoholic options. The Black Manhattan stands out on a menu that suits both date nights and after work drinks under soft lighting.

People are saying

"The cafe's specialty coffees are unique and fantastic."

"You have to try the cocktails; the menu is unique and they taste phenomenal."

"It's so cozy and nice inside, perfect for a date."

Good to know

1

Happy hour runs from 4-7pm with a great menu of drinks and appetizers.

2

Buttercup transforms into a cocktail bar after 4pm.

3

Street parking is available nearby for easy access.

03
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Japanese restaurant

Japanese restaurant offers an industrial-chic design with a quiet, spacious atmosphere perfect for dates or chats. Cocktails feature a modern twist on Japanese flavors, with the Gin Blossom as a standout. Rare ramen and Japanese beer on tap add to the vibrant vibe.

Cocktails here blend Japanese flavors with a modern twist and suit different tastes. The Gin Blossom stands out as a highlight, often praised even over the food.

People are saying

"The Japanese food, especially the ramen, is flavorful and comforting."

"The gyoza here are great and crispy."

"I loved the Midori by Moonlight and Gin Blossom cocktails."

Good to know

1

Lunch specials are available for $21.95, including a side, main dish, and drink.

2

Happy hour features discounted cocktails and appetizers, making it a great time to visit.

3

The restaurant offers a variety of Japanese dishes beyond ramen, like gyudon.

04
Southern Chicago image 1

Elegant space offers beautiful décor and a warm vibe with great music. Specialty cocktails by Adrian deliver delicious flavors while staff provide great service. Southern-inspired dishes add a high-quality touch to the inviting atmosphere.

Specialty cocktails crafted by Adrian stand out for their delicious flavors. Staff ensures satisfaction with every drink, adding to the great service and overall ambience.

People are saying

"The food here is amazing, fresh, and thoughtfully prepared."

"The desserts here are phenomenal, sealing the deal for me."

"I really enjoyed the specialty cocktails here."

Good to know

1

Happy hour offers great prices on food and drinks.

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available for guests.

05
The Staley image 1
Sports bar

Large sports bar feels like a dark basement man cave with upscale gastropub décor. Cocktails are strong and well-crafted but pricey at $16. Free arcade games add casual fun beyond watching games on huge projector screens.

Cocktails come strong and well-crafted with great flavor. Prices sit at a $16 price point, which is on the high side for a bar and grill.

People are saying

"The food here is unique, delicious, and top-notch."

"The staff here is super friendly during live sports."

"Maegan's wit and quick drinks make closing the place down easy."

Good to know

1

Reservations are not accepted on game days; plan accordingly.

2

A 20% service charge is automatically added to bills on game days.

3

Happy hour features discounted drinks and appetizers from 4-7pm on weekdays.

06
Signature Steak image 1
Restaurant

Upscale sports bar buzzes with large screen TVs and lively crowds. Signature cocktails like the spicy margarita shine with unique flavors and fair prices. Dim lounge offers a private vibe and great music for a quieter escape.

Signature cocktails stand out with unique flavors and solid craftsmanship. The spicy margarita offers a refreshing kick, and prices stay reasonable.

People are saying

"The food and drinks here are thoughtful, indulgent, and expertly executed."

"The cocktails here are delicious and perfectly balanced."

"The cocktails here are expertly executed and truly signature."

Good to know

1

Reservations are recommended, especially during peak hours.

2

Happy hour offers discounted drinks and appetizers from 4-6pm on weekdays.

3

Expect small portion sizes relative to the price.

07
Brûlée image 1
Restaurant

Warm, modern space with thoughtful decor and a spacious bar sets a lively mood. Signature cocktails shine with gin, lemon, and bergamot for a fresh taste, though some drinks are just okay. Music blends R&B at moderate volume, adding to the energetic vibe.

Signature cocktails show creative mixes. Gin drinks with lemon and bergamot offer a refreshing, not too sweet taste. Some cocktails come off as just okay.

People are saying

"The food here is so flavorful and fresh."

"The shrimp and grits at brunch were some of the best I've ever had."

"I loved the gin cocktail with lemon and bergamot; it was so refreshing."

Good to know

1

Reservations are recommended for large groups or after 10 PM on weekends.

2

Expect a wait for tables, especially during peak brunch hours.

3

Brûlée enforces a strict 90-minute table limit for diners.

08
VU Rooftop image 1
Restaurant

Rooftop spot shines with spectacular city views and a lively vibe. Cocktails are fresh and well-balanced, served in large batches. Cozy lounge and fire pits create a warm atmosphere perfect for groups and jazz lovers.

Cocktails come fresh and well-balanced, served in large batches. They stand out for their excellent quality and fit a neighborhood bar vibe.

People are saying

"The food here is great, and the staff are so friendly."

"The rooftop views of the city and lake are impressive."

"The cocktails were fresh, well-balanced, and delicious."

Good to know

1

Reservations are recommended, especially on weekends due to high demand.

2

A 20% automatic gratuity is added to all bills, regardless of party size.

3

Security checks are similar to TSA procedures before entry.

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Near South Side, Chicago

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