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New Yorkers 1st Choice
Near South Side's best

Cool spots

Places that have a genuine edge without trying too hard to be trendy.

Based on 542 Opinions
+539
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Updated May 2026
01
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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.

Fantastic food stands out with incredible Mexican dishes and excellent service that complements the dining experience.

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.

02
La Calle Tacos y Tequila image 1
Mexican restaurant

Mexican restaurant offers a vibrant and inviting atmosphere with tasteful decor and lively artwork. The space feels comfortable and clean, suited for casual dining and drinks. It draws a crowd looking for authentic Mexican flavors in a modern setting.

Food comes out quickly and stays consistently fresh and authentic. Many find the flavors excellent and the quality very good with a clear focus on authentic Mexican dishes.

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.

03
Reggies Chicago image 1
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.

Food here is delicious and pairs well with the lively bar atmosphere. Prices stay reasonable, making it easy to enjoy good eats alongside drinks.

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."

"The pulled pork here is some of the best I've had."

"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.

04
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.

Food here is consistently delicious and ranks highly in quality. Every dish delivers top tier flavors that stand out.

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.

05
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.

Signature Steak stands out with its fantastic food and drinks. The menu features an excellent burger, sides, and chicken sandwich served in a nice and cozy atmosphere.

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.

06
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.

Food comes with amazing flavors and pairs well with drinks. Service stays excellent, with helpful seating arrangements for groups.

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.

07
VU Rooftop image 1
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.

Food here is consistently delicious and excellent. The menu pairs well with great cocktails for a solid dining experience.

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.

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Near South Side, Chicago

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