Atly Logo
New Yorkers 1st Choice
Top picks in Near South Side

Cool spots

It is refreshing to spend time in a space that feels distinct and carries its own sense of character.

Based on 579 Opinions
+576
User
User
User
Updated May 2026
01
THC by Chitiva South Loop image 1
THC by Chitiva South Loop image 2
THC by Chitiva South Loop image 3
View all

Cozy cannabis store with a chill atmosphere and creative product options. Offers infused edibles that are flavorful and well-dosed. Fast service and cool visuals make it a standout local spot.

Creative local business with an inviting atmosphere and cool visuals. Offers many creative options and a variety of cool products with fast service.

People are saying

"The cafe staff is always kind and professional."

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

"The ice cream here is delicious and a must-try."

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 add a cool vibe that feels like a hidden gem. Outdoor patio and late hours make it a convenient hangout spot.

Staff bring a cool vibe that sets the tone. The spot feels like a hidden gem with a relaxed, inviting atmosphere.

People are saying

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

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

"I found the vibes and the staff here to be really cool."

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
La Calle Tacos y Tequila image 1
Mexican restaurant

Mexican restaurant shines with authentic flavors and a vibrant atmosphere. Lively artwork and a standout mural create a cool vibe perfect for casual dining and drinks.

Atmosphere feels relaxed with a standout mural inside. Artwork throughout adds an incredible, cool vibe.

People are saying

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

"The steak tacos here are flavorful and juicy."

"The atmosphere here is so cool and welcoming."

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.

04
Reggies Chicago image 1
Bar & grill

Multilevel bar and grill with live bands and a rooftop basketball hoop offers a punk rock vibe. Graffiti walls add a cool, offbeat atmosphere perfect for music lovers. Seating includes comfy balconies and lively bars, making it a chill hangout spot.

Unique bar grill with cool graffiti and an off the beaten path atmosphere. It offers a chill vibe for music enthusiasts to hang out.

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 cool dive spot with awesome vibes."

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
Sweeney Taud image 1
Barber shop

Modern space with large windows and a sleek design creates a cool vibe. Staff are welcoming and skilled with diverse hair types. Indoor cafรฉ and small pond add a relaxed, upscale feel blending grooming with spa-like comfort.

A really cool vibe and design stand out here. The owner and staff are welcoming and cool.

People are saying

"This barbershop's atmosphere is welcoming, refined, and exudes excellence."

"The atmosphere here is so classy and refined."

"Jorge gave me the best fade and line up Iโ€™ve ever received."

Good to know

1

The salon offers a variety of services for all hair types, including cuts and grooming.

2

Expect to pay around $75 for a standard haircut.

3

Warren, the owner, is known for cutting hair for both celebrities and everyday clients.

06
Casa Tulum image 1
Mexican restaurant

Mexican spot shines with live DJ and fire show for a cool, energetic vibe. Two bars with TVs keep the energy high. Great margaritas and flaming desserts make it perfect for a girls night out.

Ambience stands out with a cool vibe that fits well for a girls night. Food and drinks complement the great spot atmosphere.

People are saying

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

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

"It's a cool spot with a great vibe."

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.

07
Signature Steak image 1
Restaurant

Upscale sports bar offers a lively atmosphere with modern black-and-white decor and large screen TVs. Dim, private lounge provides an intimate vibe with great music. Signature cocktails shine in a cool urban chill setting that feels hip and inviting.

Hip, warm, and inviting atmosphere with a cool urban chill vibe. The space features a clean bar and a lively sports bar vibe that feels nicer than average.

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 urban chill vibe with tasteful decor."

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
BASSLINE || 2239 - CHICAGO image 1

Lounge boasts an open layout with a spacious dance floor and blacklight artwork that sets a colorful, chill vibe. Live DJs spin '90s and 2000s hits, keeping the energy lively yet relaxed. Groups enjoy the casual, cool setting that stays open late.

Blacklights highlight the artwork and attendees' outfits, creating a unique vibe. Walls feature art decorations that add to the overall atmosphere upstairs.

People are saying

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

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

"The artwork and blacklights here are really cool."

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.

09
VU Rooftop image 1
Restaurant

Rooftop restaurant shines with spectacular city views and a lively atmosphere featuring live jazz and fire pits. Upscale vibe makes it a cool spot for drinks, especially with the signature boss lady cocktail. Cozy lounge areas invite relaxing with friends.

An upscale vibe sets the tone here, making it a cool spot to enjoy drinks. The rooftop area adds to the atmosphere, and signature cocktails like the boss lady drink fit the scene well.

People are saying

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

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

"I thought the vibe here was really cool."

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.

10
The Staley image 1
Sports bar

Large sports bar with huge projector screens and free arcade games offers a cool vibe with friendly staff. Fans enjoy watching Bulls games in a dark basement man cave setting. Upscale gastropub dรฉcor adds a unique touch to the casual sports experience.

A cool vibe fills the space with friendly staff adding to the atmosphere. A Bulls game plays on TV, making it a popular spot for fans who can't watch at home without high costs.

People are saying

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

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

"The mozzarella sticks here are huge and delicious."

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.

Discover more

Near South Side, Chicago

Area guide
Loading Map...