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New Yorkers 1st Choice
the Loop's best

Cool bars

A drink feels better in a room that carries a distinct, intentional vibe. It is about finding a space that feels as sharp as the company you keep.

Based on 567 Opinions
+564
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Updated April 2026
01
Bar Sotto image 1
Bar Sotto image 2
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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.

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.

Cozy speakeasy vibes mix with a jazzy atmosphere and subtle lighting. The drink menu stays modern and creative, making it a cool spot to grab a drink.

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 drinks here are fantastic, modern, and creative."

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.

02
Monk's Pub image 1

Classic pub with dark wood and exposed brick creates a cozy, old-world atmosphere filled with Belgian beer memorabilia and vintage decor. The space feels packed and lively, offering a laid-back vibe ideal for socializing. Music leans toward garage rock, punk, and blues, enhancing the authentic pub experience.

Offers an outstanding beer selection with many Belgian and local options. The bar features a cozy, European tavern feel with vintage books, dark wood, and barrels. Staff are wonderful and the food includes notable items like the Monkburger and Chicago Poutine.

Rustic, charming pub design with stained glass fixtures and Germanic styling sets a cool tone. Walls covered in beer and spirit memorabilia add to the old-timey tavern vibe.

People are saying

"The beer selection here is extensive and solid."

"The food here was amazing and great."

"The bar's beer selection is extensive and diverse."

Good to know

1

Happy hour gets crowded, so arrive early to secure a spot.

2

Reservations are not accepted after 6pm, so plan accordingly.

3

Parking is available under the elevated tracks on Lake Street.

03
Momento Cantina image 1
Mexican restaurant

Space features vibrant Mexican-inspired decor with colorful lights and intricate metalwork. Atmosphere feels fun and lively, enhanced by live mariachi music and reggaeton beats. Unique self-serve tequila and mezcal stations invite guests to sample drinks at their own pace.

Sebastian's attentive service stands out at the bar. Staff regularly check in, making the experience feel more personal and engaging.

Concept for ordering stands out as very cool. The design and street artist paintings give the place a unique vibe that feels fresh and interesting.

People are saying

"The food here is delicious and fresh."

"The service for dinner here is wonderful, especially from Sebastian and Zoe."

"Sebastian at the bar made the best micheladas."

Good to know

1

Happy hour runs from 4-7pm with great deals on drinks and appetizers.

2

Friday night features live Mariachi performances starting at 8pm.

3

The venue plans to host live DJ performances in the future.

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.

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.

The spot offers a cool bar for drinking and a fun golf experience at Five Iron Golf. Staff like Mathis are professional and cool.

People are saying

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

"The food here is delicious and fresh."

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

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
Adams Street Brewery image 1

Wood-paneled sports bar with a large warm wood bar and historic vibes creates a welcoming, laid-back atmosphere. Polka music and live performances add a German Beer Hall feel, while televisions offer casual entertainment. The place stays relaxed during mid-afternoon and grows lively later in the day.

A large, warm wood bar creates a welcoming atmosphere with lots of draught beer selections including German styled drafts. The bar offers great service and full access to the historic restaurant next door.

Historic significance stands out with the site holding Chicago's first liquor license. The bar offers a cool atmosphere and a wide range of draught beer selections.

People are saying

"I enjoyed the great German-style beers here."

"This bar has a great beer selection with many German styles."

"It's a cool bar with lots of draught beer selections."

Good to know

1

Expect busy times during holidays; reservations are not required.

2

Pickpocketing incidents have been reported, so keep personal items secure.

3

Credit cards and mobile payments are accepted for purchases.

06
Bistro Monadnock image 1
French restaurant

Historic building hosts a French bistro with European charm and elegant design. Live jazz music creates a relaxing atmosphere complemented by a skilled bar offering standout cocktails. The space feels cozy and stylish, attracting those seeking a refined dining experience.

Cozy atmosphere with skilled bartenders crafting drinks. Offers wines by the glass and bottle at reasonable prices compared to other spots.

Effortlessly cool Parisian bistro vibe fills the space. Located in a historic Chicago building, the atmosphere feels both classic and fresh.

People are saying

"The escargot here is outstanding and alone worth the visit."

"The bartenders here are fantastic and have so much imagination."

"This place has a cool, historic building and atmosphere."

Good to know

1

Reservations are recommended, especially on weekends, to avoid being turned away.

2

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

3

Expect a $10 charge for each cheese on the charcuterie board.

07
O'Neil's on Wells image 1

Old-school Irish bar with big atmosphere and a dynamic crowd mixing union workers and suit types. Music stays at a comfortable volume, supporting a great buzz without overwhelming conversation. Plenty of TVs show international sports, and an outdoor seating area adds space during nice weather.

Old-school Chicago bar vibe fills the space with a big atmosphere. Bagpipe players perform atop the bar while a mix of union workers and suit types gather. The bar shows international sports and includes a pizza shop inside.

A cool little Irish pub vibe mixes with casual pizza offerings. The spot feels really cool and sits close to the train station.

People are saying

"The bar staff here are really nice and friendly."

"The pizza here has a crispy crust and great sauce."

"This is a cool little Irish pub with pizza."

Good to know

1

Expect drink prices to be high, with a PBR costing $6.50 and a well drink costing $10.50.

2

Happy hour offers great specials during the week.

3

The bar is a two-minute walk from the nearest hotel.

08
Francois Frankie Le Carousel Bar image 1

Rotating carousel bar moves slowly, completing a full turn about once per hour, creating a unique focal point. Upscale ambiance combines with comfortable seating and a perfect noise level for conversation. Jazz duo adds to the atmosphere, making it lively yet approachable.

A rotating carousel bar creates a fun and unique drinking experience. The bar offers a lively happy hour scene and a pre-theater menu that fits well for a night out before a show.

A bar shaped like a carousel moves slowly, adding a unique touch. The spot has a modern French bistro vibe that feels fresh and cool throughout.

People are saying

"The Amish chicken at this Bar is tender, juicy, and perfectly seasoned."

"The cocktails are creative and the bar looks just like a carnival carousel."

"The burger was fatty, juicy, and perfectly griddled."

Good to know

1

On Tuesdays, enjoy a $10 cocktail and oyster night with live jazz music.

2

Happy hour features discounted drinks and appetizers from 4-7pm on weekdays.

3

Expect to spend around $60 per person for a meal with drinks and tip.

09
Jazz Showcase image 1
Jazz club

Intimate jazz club with historic dรฉcor and excellent acoustics creates a cozy, relaxed atmosphere. Live performances feature talented musicians playing in a setting that honors jazz legends. Dim lighting and comfortable seating offer a balanced sound experience ideal for soaking in pure jazz.

A cozy, authentic jazz bar with a long history as the second oldest in the US. The bar serves a solid selection of drinks at reasonable prices, and the staff adds to the memorable atmosphere.

A very cool vibe fills the jazz lounge with a super cool atmosphere. The tunes played during performances add to the overall coolness of the venue.

People are saying

"I enjoyed the great live jazz performances here."

"The bar's vibe is intimate and cozy."

"It's a really cool place with a great atmosphere."

Good to know

1

Admission is $20 per person for entry.

2

Jazz Showcase does not serve food but allows patrons to bring their own.

3

It is advisable to buy tickets in advance as shows often sell out.

10
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.

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.

Cool airy decor sets a fresh vibe. Rooftop feels laid back with smoky, cool drinks and plenty of non-alcoholic options.

People are saying

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

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

"The cool airy decor here is fantastic."

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.

11
The Game Room image 1

Bar combines vintage decor with modern games like pool, shuffleboard, and skeeball. Atmosphere varies from relaxed upscale to loud and sketchy depending on the crowd. Large space offers ample seating and diverse activities throughout.

Energy stays high with people enjoying drinks and nostalgic games. Multiple bars exist inside a nice building, including a rooftop bar with great beer and games, plus pool tables and shuffleboard areas.

A cool vibe fills the space with a relaxed, upscale feel. The building has a cool history and offers fun games that add to the atmosphere.

People are saying

"It's a fun place with a lively vibe and great games."

"The food here is delicious and satisfying."

"This bar has tons of games like shuffleboard and pool."

Good to know

1

Reservations are recommended for large groups to ensure space availability.

2

The venue has a minimum food and beverage requirement for private events.

3

Expect a surcharge if you exceed the agreed-upon food and beverage minimum.

12
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.

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.

A super cool vibe sets the tone with a lively party atmosphere and friendly, welcoming staff. The place shines as a cool spot for late night eats with a very cool overall atmosphere.

People are saying

"I experienced unique, great customer service here."

"The vibes here are pretty cool and chill."

"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.

13
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.

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.

Bartenders like Tee and Chris bring a friendly vibe and make sure everyone feels cool and comfortable. Sharing drinks and good company add to the laid-back atmosphere.

People are saying

"The food here is fresh and delicious."

"Our bartender Jada was amazing and so nice."

"The drinks here are amazing and perfectly made."

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.

14
Senoritas Cantina On Dearborn image 1

Small Mexican restaurant with legit Mexican decor and Latin vibes offers both indoor and outdoor seating on a quiet street. Atmosphere is chill but music inside can be very loud. Known for fantastic margaritas and underrated vegetarian options.

Bar offers a decent variety of tequilas and seats at the bar for solo visits. It serves as a casual spot to stop in when other bars are packed.

The spot has a consistently cool vibe and a relaxed environment that stands out. It feels like a cool place to hang out.

People are saying

"The Mexican food here is authentic and delicious."

"The bartender was so amazing and attentive."

"I found the vibe here to be really cool."

Good to know

1

Happy hour runs from 3-6pm with a 20% discount on drinks.

2

Brunch is now offered on weekends with a special menu.

3

A 3% surcharge applies for credit card payments.

15
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.

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.

Cool events like karaoke nights happen throughout the week. The spot has a laid-back vibe that draws a crowd looking for a fun time.

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."

"I found this spot to be cool for its ongoing games and events."

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.

16
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.

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.

Cool vibe fills the space, shaped by the bartender and owner who set the right tone. The atmosphere feels relaxed and effortlessly stylish.

People are saying

"I thought the food was amazing and delicious."

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

"The vibe here is really cool."

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.

17
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.

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

Robotic serving trays deliver the food, adding a unique touch. The decor and setup create a distinct, cool vibe throughout the space.

People are saying

"The food here is always amazing and fire."

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

"I thought the vibe and decor here were really cool."

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.

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