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New Yorkers 1st Choice
Local picks in Near South Side

Chill spots

Made for those who seek out unhurried spaces where they can decompress at their own speed.

Based on 616 Opinions
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Updated May 2026
01
THC by Chitiva South Loop image 1
THC by Chitiva South Loop image 2
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Cozy cannabis store offers a chill atmosphere with board games and a cafe vibe. Infused edibles and desserts provide flavorful, well-dosed choices. Friendly staff create a relaxed space like Amsterdam's laid-back energy.

The spot has a chill atmosphere with a vibe like relaxed Amsterdam. People are helpful and the environment invites hanging out with board games and drinks.

People are saying

"The cafe staff is always kind and professional."

"I found this place to be really cool and creative."

"The vibe here is so chill and relaxed."

Good to know

1

The cafe is open late until 11 pm, perfect for evening visits.

2

Free Bingo happens every Thursday night, a fun way to engage with the community.

3

Expect a 20-minute wait for hot chocolate on busy weekends.

02
Prohibition THCafe - South Loop image 1

Cafe blends live music and art-lined walls for a lively, chill vibe. Staff keeps energy dope and easygoing, perfect for chatting or working. Outdoor patio and late hours add to its inviting atmosphere and convenience.

Energy stays dope with chill music setting a relaxed tone. Staff keeps things easygoing, making it a spot to chill, chat, and work comfortably.

People are saying

"The lemonade here is top-tier, with friendly and knowledgeable service."

"I loved the chill vibe and the music here."

"The infused espresso was perfect and delicious."

Good to know

1

Karaoke night happens every Thursday at 10pm with a two-drink minimum.

2

Open Mic events are held regularly, but check for cancellations.

3

Prices for pre-rolls start at $25.

03
MIKAMI IZAKAYA & RAMEN image 1
Japanese restaurant

Japanese restaurant blends industrial-chic design with a quiet setting perfect for relaxed chats. Full bar serves Japanese beer on tap and rare ramen, creating an upscale yet casual vibe ideal for chilling.

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.

People are saying

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

"The gyoza here are great and crispy."

"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.

04
Reggies Chicago image 1
Bar & grill

Multilevel bar and grill buzzes with live bands and a rooftop deck featuring a basketball hoop. Lively, loud, and dark, it also offers a chill vibe upstairs with casual eats and laid-back staff. Comfy balcony seats add to the punk rock energy.

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.

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.

05
Little Branch Cafe image 1

Cozy indoor tables and a shaded patio offer unique seating for a chill vibe. Quiet, friendly atmosphere suits casual breakfast or lunch. Spacious, modern setup keeps the mood relaxed and trendy.

Spacious seating and a casual atmosphere create a chill vibe. A modern setup and a patio add to the relaxed feel without being too loud.

People are saying

"I had the best breakfast during my business trip."

"The chilaquiles here are authentic with amazing salsa verde."

"It's a chill neighborhood place with a relaxed vibe."

Good to know

1

Finding parking nearby is difficult; most options are paid.

2

The cafe is within walking distance of the Hilton in McCormick Place.

3

There was no wait during my visit, making it a quick stop.

06
The Staley image 1
Sports bar

Large sports bar offers a dark basement vibe with huge projector screens for games. Chill atmosphere helps you unwind quietly while enjoying free arcade games and a mini game room for casual fun.

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

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.

07
Signature Steak image 1
Restaurant

Upscale sports bar with large screen TVs offers a lively vibe for sports fans and signature cocktails for drink lovers. Dim, private lounge creates a chill atmosphere perfect for casual hangouts or special nights. Food matches the mood, fitting both pregames and upscale outings.

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

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.

08
Casa Tulum image 1
Mexican restaurant

Mexican restaurant shines with live DJ and fire show for an energetic vibe. Two bars with TVs boost the lively scene while great margaritas and flavorful dishes satisfy. Cozy corners and a hip music selection keep it chill and inviting.

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

People are saying

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

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

"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.

09
BASSLINE || 2239 - CHICAGO image 1

Lounge features an open layout with a spacious dance floor and blacklight artwork that sets a chill vibe. Live DJs spin '90s and 2000s hits, creating a lively yet relaxed club atmosphere. Groups enjoy a casual, cool spot that stays open late.

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

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.

10
Williams Inn Pizza & Sports Bar image 1

Big-screen TVs create a sports-focused environment perfect for game nights. Rustic charm adds to the laid-back vibe ideal for casual lunches and unwinding. Loud music from a live DJ keeps energy high for singing and dancing.

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.

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.

11
VU Rooftop image 1
Restaurant

Rooftop restaurant shines with spectacular city views and a lively atmosphere featuring live jazz and fire pits. It offers a cozy lounge area perfect for relaxing with friends. Chill vibes come from smooth R&B and chill hip hop, making it ideal to unwind and enjoy drinks.

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.

People are saying

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

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

"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.

12
La Calle Tacos y Tequila image 1
Mexican restaurant

Vibrant Mexican restaurant offers authentic flavors in a modern setting. Casual and relaxed vibe with clean, bright seating makes it perfect for quick, casual eats. Lively artwork adds to the inviting atmosphere.

Casual, relaxed atmosphere with a clean and bright seating area. Good spot for a quick, casual eat.

People are saying

"The food here is delicious, fresh, and flavorful."

"The steak tacos here are flavorful and juicy."

"The tacos here are so tasty and well-prepared."

Good to know

1

The chips and guacamole cost $9, and the side of guacamole is the same size as Chipotle's, which costs $5.

2

Expect a busy lunch rush with potential wait times.

3

The food came out quickly, which is helpful for those needing a quick option.

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Near South Side, Chicago

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