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New Yorkers 1st Choice
Best of Near South Side

Chill bars

Made for those who prioritize a low-key environment when they head out for a drink.

Based on 555 Opinions
+552
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Updated May 2026
01
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Bar & grill

Multilevel bar and grill with live bands and a rooftop deck featuring a basketball hoop creates a punk rock vibe. Atmosphere is lively and energetic, often very loud with dark, moody lighting. Seating includes comfy balcony spots and ample bars throughout the venue.

Rooftop deck offers a sweet spot to chill with great drinks and casual eats. The vibe stays chill but rock, with a casual atmosphere and attentive, laid-back staff.

A dive bar with a unique atmosphere featuring cool graffiti and an off the beaten path vibe. The bar offers great food and a fun spot for live music in a small setting.

People are saying

"The bar food, especially the pulled pork, is some of the best I've had."

"It's a live music hub with gritty charm and energetic vibes."

"It's a super chill place to hang out with a relaxed vibe."

Good to know

1

Parking can be challenging; consider using public transport or rideshares.

2

The venue hosts live music events almost every weekend.

3

Food service ends at 10pm, so plan accordingly.

02
MIKAMI IZAKAYA & RAMEN image 1
Japanese restaurant

Japanese restaurant combines industrial-chic design with elegant touches for an upscale look and vibrant, casual vibe. Atmosphere stays quiet and spacious, fitting for romantic dates or relaxed chats. Full bar offers Japanese beer on tap and notable cocktails alongside rare ramen varieties.

Quiet setting with enough personal space supports easy chatting and chilling. The vibe stays casual and chill, mixing traditional izakaya energy with a modern cozy atmosphere.

The bar offers an impressive whiskey and scotch selection alongside a variety of sake. Service at the bar stays flawless and attentive, even when busy, making it easy to enjoy drinks paired with food.

People are saying

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

"I loved pairing the delicious starters with a beer at the bar."

"The ramen broth here is rich, creamy, and packed with umami flavor."

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.

03
The Staley image 1
Sports bar

Large sports bar with huge projector screens and plenty of TVs creates a strong focus on watching games. Atmosphere feels like a dark basement man cave with a mix of upscale gastropub dรฉcor. Free arcade games and a mini game room add casual entertainment beyond sports viewing.

A chill vibe makes it easy to unwind here. It works well for catching a game or just relaxing quietly.

A large and classy neighborhood bar offers a welcoming atmosphere without any dive bar vibes. Bartenders are friendly, fast, and knowledgeable, providing solid drink recommendations.

People are saying

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

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

"Briayna, our trivia host, made the night a full-blown event."

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.

04
Signature Steak image 1
Restaurant

Upscale sports bar with modern black-and-white decor and large screen TVs creates a lively, sometimes loud atmosphere. Dim, private lounge offers a contrasting intimate vibe with great music. Signature cocktails and well-crafted drinks stand out amid close seating and energetic crowds.

Space suits both casual hangouts and special occasions with ease. Food matches the vibe, fitting for chill pregames or upscale nights out.

Bar offers a moody ambiance with a great R&B playlist and big screens showing sports all night. Unique dill sauce stands out for dipping fries and topping the chicken sandwich.

People are saying

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

"The cocktails here are delicious and perfectly balanced."

"It's got this cool, upscale chill vibe, perfect for a classy dinner."

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.

05
Casa Tulum image 1
Mexican restaurant

Mexican restaurant with beautiful decor and an energetic vibe featuring a live DJ and upbeat music. Two bars with TVs add to the lively atmosphere, complemented by a fire show and flaming desserts. The place draws a crowd enjoying great margaritas and flavorful dishes in a clean, vibrant setting.

Calm and cozy atmosphere sets a chill tone here. Music selection adds to the hip vibe, making it great for casual or fancier dinners.

Two bars offer ample seating even on weekdays. Staff like Rafael and Bar Manager Nia provide efficient, welcoming service that enhances the experience.

People are saying

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

"Nia at the bar was amazing and made great suggestions."

"The vibe here is so chill and has a hip atmosphere."

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.

06
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Restaurant

Rooftop restaurant offers spectacular city views and a lively atmosphere with live jazz music and fire pits for warmth. Seating includes a cozy lounge area ideal for relaxing with friends. The venue combines indoor and outdoor spaces, creating a vibrant setting for group gatherings.

Good music sets a chill vibe with R&B and 2010-2020 chill hip hop playing. The spot offers a relaxed atmosphere to drink and enjoy the city view.

A full bar offers quick, knowledgeable bartenders and a wide selection of drinks. The space includes a large dance floor, an indoor restaurant, and an outdoor area with breathtaking views that create a lively atmosphere.

People are saying

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

"The bar has incredible views and a chic ambiance."

"It's a chill spot with good R&B and hip hop music."

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.

07
Williams Inn Pizza & Sports Bar image 1

Big-screen TVs cover every wall, creating a sports-focused environment with rustic charm. Loud music from a live DJ energizes the space, encouraging singing and dancing. Seating is ample, designed for casual family dinners and lively game nights.

A laid-back sports bar vibe blends with rustic charm to create a chill atmosphere. It suits casual lunches, unwinding after work, and socializing while watching games.

A very large bar creates an intimate, neighborhood feel with a warm, inviting ambiance. Staff provide excellent service even when busy, making it a lively spot for sports and socializing.

People are saying

"This deep dish pizza is amazing and straight out of the oven."

"The bar staff treated me like a regular with a smile."

"It's a great spot to chill and meet people."

Good to know

1

Happy hour runs from 4-7pm on weekdays with great drink specials.

2

Parking is difficult; consider using a ride share or park a block away.

3

A DJ performs on Friday nights, creating a lively atmosphere.

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BASSLINE || 2239 - CHICAGO image 1

Lounge offers an open layout with a spacious dance floor and blacklight-enhanced artwork that creates a colorful, chill vibe. Live DJs spin mostly '90s and 2000s hits, fueling a lively yet relaxed atmosphere. Groups gather comfortably in this casual, cool setting that stays open late.

Casual and chill vibe sets the tone here. It works well for a club atmosphere that lets people unwind.

Space feels nice and spacious for dancing but the bar itself is just a room with limited variety. Service can be slow, requiring moving to the center to get attention.

People are saying

"I found the bar to be nice and spacious for dancing."

"The nightclub has a cool, attractive atmosphere for dancing."

"It's a nice chill spot with a casual vibe."

Good to know

1

Entry is $20 on Fridays, increasing to $25 before midnight.

2

Parking is limited in the area, so plan accordingly.

3

The venue has no elevator, which may affect accessibility.

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Near South Side, Chicago

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