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New Yorkers 1st Choice
Guide to the Loop

Chill bars

A quiet bar is the only place to go when the evening calls for a chill drink.

Based on 579 Opinions
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Updated April 2026
01
Legato Lounge image 1
Legato Lounge image 2
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American restaurant

Art deco hotel lobby sets a stylish, cozy atmosphere with a retro-modern vibe. Music stays low, creating a chill yet classy energy ideal for unwinding or casual conversation. Well-crafted signature cocktails and a spacious bar area attract a relaxed, upscale crowd.

A cool mix of retro and modern sets a super chill yet classy atmosphere. It suits unwinding after work or having chill drinks with colleagues.

Stylish and cozy with a roaring 20s inspired vibe, this bar offers well-crafted cocktails and a friendly, attentive staff. The menu has a nice variety and the seating area is spacious and comfortable.

People are saying

"Their signature cocktails are inventive and delicious."

"The bar staff here is so friendly and attentive."

"The cocktails here are art, and the bartenders really know their stuff."

Good to know

1

The bar is open every day from 4 pm to 11 pm.

2

The restroom is spotlessly clean.

3

The menu has a nice variety without being overwhelming.

02
Kasey's Tavern image 1

Classic dive bar with dark wood decor and extensive beer selection including rare taps like Pabst Blue Ribbon and Belgian beers. Friendly, down-to-earth vibe with a lively local crowd and rock music playing from a jukebox. Offers outdoor seating and allows bringing in food, featuring popular pizza and crispy wings.

Dark wood and cozy seating create a relaxed vibe. The crowd stays chill without feeling cramped, perfect for watching a game or chatting over drinks with jukebox music in the background.

Classic neighborhood pub vibe with no frills atmosphere and a lively local crowd. Offers excellent service, a solid selection of beers on tap including Guinness and craft options, and crispy, saucy chicken wings.

People are saying

"They have a great beer selection with tons of options."

"It's a chill, no-frills spot to catch a game and hear your friends."

"This bar has a great selection of beers and spirits."

Good to know

1

Contactless pay isn't available at Kasey's Tavern.

2

Customers can bring in outside food if they prefer.

3

Kasey's Tavern has several gluten-free options, including ciders and beers.

03
Bar Sotto image 1

Hidden underground bar with soft red glow and jazzy atmosphere creates an intimate, cozy vibe. Space feels mysterious and character-rich, attracting an upbeat crowd for fun nights out or romantic dates. Creative cocktails and unique design details add to its distinct charm.

Warm, inviting atmosphere with low lighting and fun music creates a chill vibe. Service stays casual and attentive, matching the relaxed setting.

A basement bar with dark disco vibes offers expertly crafted cocktails and tasty bar snacks. Friendly, knowledgeable staff create a welcoming atmosphere that feels like home.

People are saying

"The bar staff here feels like family and makes you feel right at home."

"The cacio e pepe arancini were flavorful and a must-try."

"The atmosphere is so chill with warm, inviting lighting."

Good to know

1

Happy hour offers discounted drinks and bites after work.

2

The bar features a rotating menu of small shareable plates and pasta.

3

Reservations are recommended for busy evenings, especially weekends.

04
Five Iron Golf image 1
Indoor golf course

Indoor golf facility offers top-notch simulators and luxury seating in a modern, upscale setting. Atmosphere stays chill and lively, with plenty of space and a welcoming vibe. Amenities include a full bar, numerous TVs, and social areas like a pool table and putting green.

Atmosphere stays chill throughout. Lessons with Cole and Sean keep things relaxed and easygoing.

Spacious and pleasant main bar area invites long chats and drinks. Food and drinks stand out with exceptional quality and a cool vibe for hanging out.

People are saying

"The golf staff here are genuinely fun and know how to treat you right."

"The bar staff here is so welcoming and friendly."

"The staff here is so chill and welcoming."

Good to know

1

Happy hour runs from 3 to 6pm with great food and drink deals.

2

Trivia night takes place every Tuesday at 8pm with a $5 entry fee.

3

The all-you-can-eat wings cost $5 during happy hour.

05
Cardozo's Pub image 1
Italian restaurant

Basement pub channels old school Chicago with walls lined by legal textbooks, creating a divey yet nostalgic atmosphere. Dim lighting and chill vibes make it a cozy spot for casual drinks and relaxed conversation. The crowd tends to enjoy a laid-back, unpretentious setting away from upscale venues.

Cozy and dimly lit ambiance creates a chill vibe ideal for relaxing with friends or a casual date. The setting invites unwinding and soaking in the local atmosphere with a cold drink.

Chill and dimly lit vibes create a laid-back atmosphere for drinks. Friendly service enhances the experience at this hidden gem dive bar.

People are saying

"This pub feels like a hidden gem, perfect for a laid-back drink."

"I found this place to be a great local bar."

"The vibes here are so chill and dimly lit, perfect for relaxing."

Good to know

1

Expect a 20% automatic gratuity for parties of two or more.

2

Happy hour features $5 call drinks and draft beer on Mondays.

3

On Wednesdays, enjoy a burger, fries, and a beer for $10.

06
S2 Express Grill Downtown image 1

Restaurant combines unique decor with a warm, welcoming vibe and top-tier music including hip-hop, R&B, and afrobeats. Atmosphere feels both like a casual takeout spot and a lively club under the right circumstances. Clean environment supports a positive, chill energy throughout.

Atmosphere feels very chill with great music and a relaxed vibe. It suits casual dinners or late-night hangs with frozen drinks and photo moments.

A friendly bartender creates a welcoming vibe behind the bar. This spot stands out as a hidden gem for those avoiding traditional clubs and bars.

People are saying

"I experienced unique, great customer service here."

"The lamb chops here are seasoned well and so tender."

"The bar staff here is so friendly and attentive."

Good to know

1

Happy Hour runs until 7pm with affordable drinks for dine-in only.

2

Live DJ performs on Taco Tuesdays, creating a lively atmosphere.

3

Expect a fun vibe on Fridays when the DJ is present.

07
The L Station image 1
Restaurant

Small, beautifully decorated restaurant offers a cozy yet elegant atmosphere with an intimate feel. Live DJ spins strictly R&B music, creating an upbeat and fun vibe that keeps energy lively. Known for spectacular lamb chops, perfect margarita flights, and a warm, welcoming ambiance.

Atmosphere feels very chill and cozy with a pleasant vibe. It suits casual meals and hanging out with friends.

Jada J crafts drinks that match personal tastes and creates a welcoming, family-like atmosphere at the bar. Candice handles busy times smoothly, ensuring good service during crowded Sundays.

People are saying

"The food here is fresh and delicious."

"Our bartender Jada was amazing and so nice."

"It's a cozy and casual place with a nice, chill atmosphere."

Good to know

1

Reservations are required for parties of 10 or more.

2

Expect a two-hour wait without a reservation.

3

The kitchen closes at 7pm, so arrive early.

08
Seville Chicago image 1
Restaurant

Rooftop restaurant offers stunning city views and a relaxed atmosphere with friendly staff. The space features beautiful ambiance suitable for quiet meals or lively happy hours. Cocktails and small plates complement the setting, creating a charming dining experience.

Atmosphere feels chill and easy going with a cozy, elegant vibe. Service stays top-tier while keeping things casual.

Showplace bar features wall tiles and hanging lights that create a strong visual appeal. It offers great views at night and allows dining without a reservation.

People are saying

"You'll love the inventive cocktails, many are sweet."

"The drinks here are solid, and the food menu is varied."

"The food here is cooked to perfection, so juicy and flavorful."

Good to know

1

Happy hour runs from 3:30 to 5:30pm on weekdays.

2

Happy hour offers great deals on food and drinks.

3

The restaurant is located on the 16th floor of the Hilton hotel.

09
Franklin Tap image 1
Restaurant

Expansive layout with many high-top tables and a dog-friendly patio creates a relaxed setting. Multiple TVs show sports, attracting a diverse afterwork crowd with a lively vibe. Over 100 beers on tap and affordable menu complement the casual atmosphere.

Daily drink specials create a relaxed atmosphere that helps with unwinding. The spot offers a very adult chill vibe paired with good food and drinks.

Servers are kind and let people use the spot like a bar while waiting. It offers a huge selection of taps, perfect pours of spirits, and delicious pub fare with great service.

People are saying

"The food here is excellent, tasty, and solid."

"The bar food here is great, especially the killer burgers."

"It's a super laid-back and chill spot to unwind."

Good to know

1

Happy hour runs every day with great deals on drinks.

2

Weekend brunch is available with special menu items.

3

Daily drink specials make it easy to unwind after work.

10
All Star Seafood and Sports image 1

Sports bar filled with numerous big screen TVs showing games loudly, creating a high-energy atmosphere where conversation requires shouting. Seafood dishes stand out as top-quality offerings, complementing the laid-back and friendly vibe favored by sports fans.

A chill environment filled with TVs makes it easy to catch every play. It suits a casual date or a relaxed night with friends.

Seafood stands out with great quality and flavors not typical for a sports bar. The atmosphere combines a nice restaurant feel with the casual vibe of a sports bar.

People are saying

"You can grab tasty food while watching live sports on the many TV screens."

"This sports bar has tons of big screen TVs for watching games."

"It's a chill environment with huge TVs everywhere."

Good to know

1

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

2

Salsa lessons are offered on Wednesdays, followed by a Latin dance night.

3

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

11
Reserv image 1
Restaurant

Rooftop bar offers breathtaking views and a cozy lounge creates an intimate setting. Music plays loudly with a live DJ during brunch, setting a lively atmosphere that suits both unwinding and starting a night out.

Rooftop bar offers a great spot to unwind with cocktails and great music. Downstairs feels chill and safe, while upstairs brings a faster-paced energy.

Cozy and intimate, the lounge offers a rooftop bar that serves as a great spot to unwind. Friendly bartenders help secure a good spot even on busy nights.

People are saying

"It's packed for live sports, especially the Bears games."

"You can unwind over a cocktail in this cozy, intimate lounge."

"The bar staff was super friendly and welcoming."

Good to know

1

Trivia night happens regularly, providing a fun atmosphere for guests.

2

Street parking is available, along with nearby garages for convenience.

3

The steak skillet costs $14, offering great value for a meal.

12
Cantina on Madison, Casual Mexican Restaurant & Bar, Voted #1 Tacos image 1

Mexican restaurant with quaint decor and beautiful murals creates a cozy, laid-back vibe. Indoor and outdoor seating offer a chill atmosphere suitable for relaxing after a busy day. The place stays quiet and welcoming, making it easy to enjoy the surroundings.

Laid-back and welcoming vibes create a chill spot perfect for relaxing after a long day. Great for friends outings or a girls night with a relaxed atmosphere.

Bar manager Jesus creates a welcoming vibe with friendly chats and humor. Bartenders JP and Jen provide great service while guests enjoy food, drinks, and atmosphere at the bar.

People are saying

"I thought the food was amazing and delicious."

"The drinks and tacos at the bar are delicious."

"It's a chill spot with a welcoming vibe."

Good to know

1

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

2

Taco Tuesday features select tacos for $2 each.

3

Live DJ on Saturday evenings creates a vibrant nightlife atmosphere.

13
The Marq image 1
Restaurant

Stylish restaurant and bar with a modern interior and spacious, beautifully appointed rooms. Atmosphere balances classy and laid-back vibes with a pleasant, quiet bar area that encourages conversation. Features include off-sound televisions and a setup that supports group dining and socializing.

A chill yet active atmosphere creates a casual vibe. Food offers casual American dishes with an okay-to-good taste, paired with great service.

Stylish setting with a modern interior creates a great atmosphere for drinks. The bar offers an excellent program and pairs well with the modern cuisine.

People are saying

"The food here is delicious and creative."

"The food here is really good, especially the burger and fries."

"The food here is delicious and creative."

Good to know

1

The Marq can host events for up to 100 people with excellent service.

2

Happy hour is available, making it a great spot for after-work gatherings.

3

Street parking is available around the corner on Dearborn.

14
Momento Taquerรญa image 1
Taco restaurant

Modern taco restaurant offers a vibrant atmosphere with authentic Mexican decor and a self-serve tequila and mezcal bar. The space combines a fast-casual setup with a separate sit-down dining area, creating a lively and welcoming vibe.

A separate, gorgeous sit-down dining area offers a chill vibe away from the fast-casual front. It suits a casual date or hanging out with friends.

A self-service bar offers a variety of beers to try. Bar placement limits tables and creates circulation pinch-points. Staff at the bar lack detailed knowledge about drinks.

People are saying

"These tacos taste authentic, like they're straight from Mexico City."

"The tacos and salsas here have excellent flavor."

"These tacos are like works of art, each one totally unique."

Good to know

1

Happy hour offers a $10 special that includes a full meal with tortillas.

2

The restaurant is open late for evening dining.

3

They have a vegetarian version of the veggie birria available.

15
Millennium Hall Restaurant image 1

Architecture features Frank Gehry's dancing metal design with indoor and outdoor seating offering views of the ice rink and cityscape. Atmosphere ranges from festive and chill to lively with large projection TVs showing sports. Popular for group outings and casual dining with a bar-focused vibe.

A chill vibe fills the space, making it easy to relax after a busy day. It suits a casual night out with a laid-back atmosphere.

A large bar with a huge projector TV creates a lively spot for watching games. Bartenders like Ivan, Omar, Lilly, and Jesus deliver well mixed drinks and warm hospitality with attentive service.

People are saying

"Chef David's pizza making class was so fun and awesome."

"The bar staff are attentive, kind, and provide well-mixed drinks."

"It's a chill place to relax after exploring the city."

Good to know

1

Reservations are recommended for pizza-making courses and private events.

2

Happy hour runs from 4-6pm with discounted drinks and appetizers.

3

Karaoke night starts at 10pm on Thursdays with a two-drink minimum.

16
Wilma's Famous BBQ & Tavern image 1
Barbecue restaurant

Barbecue restaurant combines robotic food delivery with a live DJ playing old school R&B, creating a lively and modern vibe. Walls display Chicago-themed artwork honoring athletes and entertainers, adding local character. Spacious seating supports a sports bar atmosphere with a slight Black Art influence.

A chill vibe fills the space with a nice ambiance that suits relaxing downtown. The atmosphere stays consistently great for unwinding.

Bar features excellent service with attentive staff. It offers a famous BBQ selection alongside a lively tavern atmosphere.

People are saying

"The food here is always amazing and fire."

"Pedro's friendly service at the bar always made my day."

"The vibe here is really chill and the music creates a good atmosphere."

Good to know

1

Happy hour features $10 cocktails and small plate combos.

2

Expect small portion sizes during happy hour.

3

The restaurant automatically adds gratuity to all bills.

17
LH Rooftop image 1
Restaurant

Rooftop bar offers unparalleled city views including river and Gothic architecture. Atmosphere is lively with loud music, making conversation difficult. Outdoor space features igloos and fire pits, with indoor area hosting a live DJ to maintain energy.

A chill vibe fills the rooftop with a cozy fireplace and a skyline view. Staff stay casual and pleasant, making it easy to unwind with solid food and a nice atmosphere.

Busy bar with friendly bartenders creates a welcoming atmosphere. The rooftop setting offers a great environment and views while staff remain accommodating and kind even during peak times.

People are saying

"The rooftop city views are stunning and beautiful."

"The rooftop bar has stunning city views."

"The rooftop vibe is nice and chill with a spectacular view."

Good to know

1

Reservations are required to secure a table at LH Rooftop due to limited space.

2

Expect long wait times during peak hours, especially on weekends.

3

Bring your ID as it is required for entry; no photos accepted.

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