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New Yorkers 1st Choice
Best of Chicago

Night lounges with live music

You want a late-night atmosphere where the music is live and the energy is constant.

Based on 727 Opinions
+724
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Updated May 2026
01
Barrel cheese & wine | cocktails | Event Space image 1
Barrel cheese & wine | cocktails | Event Space image 2
Barrel cheese & wine | cocktails | Event Space image 3
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Speak-easy bar with dim lighting and comfortable lounge seating creates an intimate, cozy atmosphere ideal for quiet conversation. Upstairs event space offers a mingle-friendly setup with leather couches and high-top tables. Outdoor patio is dog friendly and opens to the sidewalk, blending indoor and street vibes.

Dim lighting and velvet lounge chairs create a cozy, low key atmosphere. Comfortable seating and beautiful decor make it easy to talk and suitable for dates.

Talented live music plays regularly, including on Wednesdays. The setting features sultry decor and pairs well with quality drinks and yummy charcuterie.

People are saying

"I loved the wine selection, especially with the cheese boards."

"The Night Lounge has a warm, dim-lit atmosphere with cozy seating."

"I loved the talented live music that matched the wine selection."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted drinks.

2

Live music performances occur on Wednesdays and Thursdays.

3

The venue offers a spacious event space suitable for 40-50 guests.

02
Rosa's Lounge image 1
Live music venue

Small, intimate venue offers live blues and jazz music with local talent on stage. Atmosphere feels cozy and welcoming, reminiscent of classic blues clubs. Shared tables and a dance floor create a relaxed, friendly environment where every seat feels close to the action.

Live music here is authentic Chicago blues with a raw, soulful vibe that feels like a personal jam session. The crowd is electric and welcoming, and the staff is friendly with great drinks.

Live Jazz and blues fill the room, creating a vibe that keeps the place rocking. The music moves you whether you're a blues fanatic or just looking for a memorable night.

People are saying

"You can catch authentic Chicago blues and feel the passion of the music."

"It's the best blues bar for authentic music and soul."

"The live music here is soulful and moves you."

Good to know

1

Tickets are required to enter Rosaโ€™s Lounge but can be purchased at the door.

2

Live blues performances occur five nights a week, featuring various artists.

3

Parking is on the street, so consider using public transport to avoid tickets.

03
Lemon image 1

Bar combines live music with an upscale cocktail lounge vibe in a cozy, low-light setting. Space includes multiple seating areas and a patio, creating a relaxed yet lively atmosphere. Music volume balances well for both listening and conversation.

Lemon blends a lively atmosphere with live music and an upscale cocktail lounge feel. It offers unique drinks with a chill lounge vibe.

Great bands play here with phenomenal live music at just the right volume. The spot combines casual ambience with a cocktail lounge vibe, making it ideal for enjoying drinks and tunes.

People are saying

"The cocktails here are thoughtful, creative, and perfectly balanced."

"The cocktails were incredible and very well made."

"The cocktails here are unique and expertly crafted."

Good to know

1

Live music performances occur from Thursday to Saturday, featuring various bands.

2

Happy hour runs from 4-7pm with $5 shots and beers.

3

Bingo night is hosted every Wednesday at 8pm with a small entry fee.

04
Tortoise Supper Club image 1
American restaurant

Elegant supper club blends live jazz music with a cozy, lively atmosphere featuring dark wood and colorful jazz-inspired wallpaper. Dining spaces include a private room with a bar, creating intimate vibes amid a bustling crowd. The setting combines elements of a jazz club and restaurant for a unique experience.

Live jazz music plays in the lounge, creating a cool vibe for gatherings. The space fits about 100 guests and works well for private events and welcome receptions.

Excellent live jazz band performances create a vibrant atmosphere. A larger space called The Lounge hosts live music for about 100 guests during welcome receptions.

People are saying

"The food at these dinner spots was spectacular and delicious."

"The live music here is amazing, especially the cocktails."

"The Night Lounge staff were so accommodating and attentive."

Good to know

1

Reservations are required for private events and should be made well in advance.

2

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

3

Valet parking costs $16 for three hours, making it convenient for guests.

05
Qs Lounge image 1
Lounge

Lounge offers a cozy outdoor heated patio tent with televisions and a live band alongside a DJ playing great music. Atmosphere stays chill and friendly, attracting a mature, seasoned crowd who enjoy laid-back vibes and dancing. Space suits private parties and after-work drinks with a safe, trouble-free environment.

A mature and relaxing lounge with a great sound system and an outdoor patio with a TV. Offers excellent food and entertainment and hosts activities like Bingo in a lively atmosphere.

Live bands bring a great vibe with amazing performances. Music pairs well with the food, making it a fun spot to chill.

People are saying

"The bartender Cruz made my drinks perfectly and was so attentive."

"I loved the nice atmosphere and mature, relaxing vibe."

"The drinks Cruz made were so satisfying."

Good to know

1

Parking can be a challenge if there is a large party.

2

All street parking is available, but avoid the bus lane.

3

The lounge is for mature adults only.

06
The California Clipper image 1

Vintage lounge with art deco decor and leather booths creates a timeless atmosphere. Live jazz and DJ sets energize the space, with a dance floor and two bars supporting a lively crowd. Ambiance shifts from chill cocktail vibes to a bustling dance scene as the night progresses.

A beautiful lounge with a chill cocktail vibe and great music. It has a history of good cocktails under several owners.

Great live music plays almost every night with a cool setup that includes DJs and performances. The vibe feels lively and the music pairs well with drinks and the menu.

People are saying

"The cocktails here taste like liquid history."

"I loved the great live music and vibes here."

"It's a beautiful night lounge with great music."

Good to know

1

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

2

The venue hosts a $5 cover charge on weekends for DJ events.

3

Happy hour runs from 5-7pm on weekdays with discounted drinks.

07
Clara image 1
Cocktail bar

Cocktail bar with industrial art deco style and live jazz music creates a cozy, inclusive atmosphere where seating adjusts to the vibe. The space feels upscale but unpretentious, attracting a diverse crowd who enjoy crafty cocktails and engaging entertainment.

Upscale yet unpretentious vibe fits well with the neighborhood's character. Lounge jazz creates a smoky atmosphere reminiscent of classic spots, adding to the relaxed but refined feel.

Live music fills the spacious, LGBTQ-friendly bar on many nights, creating a lively atmosphere. The artist-owned spot pairs crafty cocktails with a genuinely welcoming vibe and often gets packed.

People are saying

"The spicy margarita was a highlight, truly spicy and delicious."

"I loved the live music and the creative craft cocktails."

"The live music and cocktails at the Night Lounge were amazing."

Good to know

1

Happy hour runs from Wednesday to Sunday, between 4 and 6 PM.

2

Clara offers live music on Fridays and Saturdays.

3

Cocktails cost $15 each, with a variety of options available.

08
Mastro's Steakhouse image 1
Fine dining restaurant

Elegant dining space features dim, cozy lighting and live music performances that create a romantic, upscale atmosphere. The lounge offers an upbeat vibe with talented singers and pianists providing background entertainment. Seating is close together, enhancing a lively, intimate feel.

Live music plays every night, creating an upbeat atmosphere in the lounge. The beautiful lounge area offers a relaxing spot with attentive and quick service.

A talented piano player and singer performs live, creating a personal touch by singing requested songs and celebrating birthdays. The venue features a large bar with a wide selection of alcohol, good seating, and well-lit spaces with TVs and music.

People are saying

"The steak here is amazing, with attentive and friendly staff."

"The live music here is pretty cool and adds to the atmosphere."

"The steaks at Night Lounge melt in your mouth with exceptional flavor."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted appetizers.

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available and recommended for convenience.

09
Pour Decisions Chicago image 1

Live jazz music fills the space with top-tier performances while multiple large TVs broadcast sports loudly, creating a conflicted atmosphere. Upstairs offers a speakeasy vibe with a pool table, piano, and private party rooms featuring stylish decor and a full bar. The crowd enjoys specialty cocktails and highly praised wings, blending lively energy with casual comfort.

Upstairs lounge features a pool table, piano, and sexy mood lighting. It serves as a distinct space separate from the main bar area.

Live jazz plays on weekends, creating a chill vibe. Options include watching sports or playing pool while enjoying live music and drinks.

People are saying

"The bar staff here really make sure you're taken care of."

"I vibed to the live music on the weekends."

"The upstairs lounge has a sexy mood lighting and a piano."

Good to know

1

Wednesdays feature $20 all-you-can-eat wings, a popular deal.

2

Thursdays offer an $8 burger with fries and $5 domestic drafts.

3

Trivia night happens every Wednesday, adding to the midweek fun.

10
Redhead Piano Bar image 1

Piano bar offers live piano music with a phenomenal, engaging pianist in a small, crowded space that encourages standing and dancing. An outdoor cigar lounge provides additional seating with couches and ashtrays. The atmosphere is lively and packed, creating an intense but vibrant vibe.

Speak-easy style cigar lounge offers a cozy, calm atmosphere with a well-stocked selection. Staff provide attentive service, and management often mingles in the lounge, adding to the welcoming vibe.

Live music features phenomenal piano performances with artists who take requests and interact with the crowd. The music creates a great late night vibe that lasts into the early morning.

People are saying

"This piano bar is the perfect spot to end your night."

"It's a perfect spot for fun activities to end your night."

"The live music here creates a great late-night vibe."

Good to know

1

Expect large crowds on weekends, especially after 10 PM.

2

Reservations are recommended for special events or large groups.

3

Happy hour offers discounted drinks from 4 PM to 7 PM on weekdays.

11
Cary's Lounge image 1

Neighborhood pub with eclectic decor and a laid-back vibe offers live Americana music and a well-maintained pool table. Outdoor patio provides a relaxed space often visited by a friendly cat. Atmosphere stays friendly and welcoming, attracting open-minded locals who enjoy good humor and art.

Cozy, laid-back vibe with great art and fun entertainment. An outside lounge area exists but feels out of place in the neighborhood.

Live music happens in the back room with performances from a few different bands. Events like trivia and bingo often accompany the afternoon shows, creating a lively atmosphere with on point vibes.

People are saying

"It's a great neighborhood bar where you can hang out and meet interesting people."

"I caught some live music and the vibes were on point."

"The Night Lounge staff were super welcoming and personable."

Good to know

1

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

2

Live music events often start in the afternoon on weekends.

3

Food delivery is allowed, but limited food options are available on-site.

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