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Live music speakeasies

Made for those who want to hear live music in an intimate, low-profile setting that feels like a secret.

Based on 616 Opinions
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Updated April 2026
01
The Quarry Thornton image 1
The Quarry Thornton image 2
The Quarry Thornton image 3
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Quaint bar with nostalgic decor and an outdoor patio creates a welcoming atmosphere. Live music and a 1920s-style speakeasy in the basement add unique entertainment and event spaces. The vibe is warm and lively, attracting music lovers and those seeking a comfortable, engaging setting.

Talented musicians perform regularly, creating a great atmosphere for live music. The venue pairs music with drinks and food, making weekends lively with both games and live bands.

A hidden gem speakeasy sits in the basement, offering an authentic 1920s vibe perfect for private parties. The space feels intimate and fascinating, with owners often showing the speakeasy side to guests.

People are saying

"I found the food here to be amazing and delicious."

"The live music here is always on point."

"The Speakeasy staff makes you feel like family."

Good to know

1

Bingo night happens every Wednesday, attracting a lively crowd.

2

Karaoke contests take place every Thursday with a two-drink minimum.

3

Open mic night is hosted every Thursday, showcasing local talent.

02
Des Plaines Theatre image 1
Live music venue

Small, beautifully restored venue with intimate seating and excellent sound quality creates a professional, relaxing atmosphere. Upstairs speakeasy features 1920s velvet decor and antique touches, adding nostalgic charm. Crowded lobby contrasts with spacious seating and free parking nearby.

Refurbished old theatre offers great live shows with a focus on Wednesday & Thursday Nights Live Jazz. The venue includes a speakeasy that features live music, creating a neat atmosphere for concerts.

A hidden speakeasy sits on the second floor behind a bookshelf door, featuring a 1920s vibe and live music. It offers a secret entrance and a balcony overlooking the stage.

People are saying

"I found the theater beautiful and comfortable."

"The speakeasy upstairs has a cool 1920s vibe."

"It's a great place to see live music and shows."

Good to know

1

Free parking is available behind the venue.

2

The theater hosts live music events regularly.

3

A bar and pizza place are located inside the theater.

03
Stardust image 1

Two floors offer distinct atmospheres with dueling piano performances upstairs and a DJ-driven speakeasy downstairs. The space combines futuristic and astrology-themed decor with energetic, authentic Chicago vibes. Music ranges from jazz and blues to R&B, creating a lively and friendly environment.

Live music features a mix of karaoke, live piano singing, and DJ sets that energize the space. The music creates a lively atmosphere in this cocktail bar and late night spot.

A DJ spins music downstairs in the Dragon Speakeasy. The vibe centers on live DJing creating a lively atmosphere.

People are saying

"The bar staff here are super friendly and welcoming."

"I loved the fantastic live music and the energy it created."

"I experienced Chicago's best jazz and blues at the speakeasy."

Good to know

1

Parking garages are nearby, and street parking is available.

2

Credit cards and mobile payments are accepted, but cash may be preferred.

3

The venue features live jazz, blues, and piano performances regularly.

04
933 Speakeasy image 1

Small bar on the third floor offers a 1920s speakeasy feel with impeccable decor and a hidden vibe. Atmosphere stays warm and laid back, with classic cartoons playing quietly and live music on weekends. Space includes a basement elevator for easy access and features both lively and quiet areas.

Live music plays from Thursday to Sunday, creating a lively weekend vibe. Enjoy great drinks, cigars, and consistent live performances during these nights.

Atmosphere captures a 1920s speakeasy feel with lots of little secrets to discover. Bartenders mix a great drink selection including unique shots like the Ghost of Minnette.

People are saying

"The bartenders here craft delicious cocktails with friendly, knowledgeable service."

"The Speakeasy atmosphere here is amazing and so warm."

"I enjoyed the awesome live music on weekends."

Good to know

1

Reservations are not required but recommended for larger groups.

2

The venue can get busy later at night on weekends.

3

Live acoustic music is featured every Friday night.

05
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.

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

Upstairs offers a modern day speakeasy vibe with a hidden, intimate feel. The space impresses with its secretive layout and classic cocktail focus.

People are saying

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

"This speakeasy is a cool spot with great music and vibes."

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

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.

06
Arcada Theatre image 1
Live music venue

Historic theater offers an intimate setting with excellent acoustics and a vintage atmosphere. Multiple floors include a speakeasy lounge and diverse bar areas, creating varied experiences within one venue.

An intimate venue with a vintage atmosphere hosts live bands and shows. Multiple floors offer varied entertainment, including a speakeasy and reserved party spaces.

Upstairs offers an amazing decor and a great atmosphere that pairs well with shows. Dinner and entertainment here are consistently fantastic and enjoyable.

People are saying

"You'll love the performing arts here; they always book amazing acts."

"The speakeasy's atmosphere sucked me into history and uniqueness."

"It's a great place for live music and intimate shows."

Good to know

1

Parking is first come, first served, so arrive early to secure a spot.

2

Seating charts are available online; check them before your visit.

3

The sound quality can vary, so choose your seats wisely for the best experience.

07
Cellar 26 image 1
American restaurant

Speakeasy-style basement venue with dim lighting and vintage decor creates a Prohibition-era atmosphere. Live piano and jazz performances add quiet, elegant energy that supports conversation. Hidden entrance and password access enhance the sense of exclusivity and intrigue.

Live music features piano performances that include playing songs on request. The ambiance blends live piano music with a variety of drinks.

A throwback speakeasy style creates a warm, quaint, and vintage atmosphere. Entry requires a password, adding an air of mystery and intrigue from the start.

People are saying

"The food here is a hidden gem, tucked away and hard to find."

"It's like stepping back into the prohibition days with this speakeasy vibe."

"You get a password for this speakeasy experience with secret instructions."

Good to know

1

Reservations are required to receive the secret phrase for entrance.

2

Expect a 20% gratuity added to checks for tables of six or more.

3

The family-style menu simplifies selection for groups dining together.

08
Amore Mio Restaurant & Piano Bar image 1

Italian restaurant combines elegant ambiance with a warm, inviting decor featuring live jazz music and a speakeasy piano bar downstairs. Atmosphere feels relaxing and beautifully decorated, drawing a crowd that appreciates both food and music in a stylish setting.

A four-piece band plays live jazz downstairs, creating a lively atmosphere. The piano bar offers cocktails alongside live jazz performances after dinner.

A speakeasy bar sits downstairs, offering a cozy, hidden vibe. Live violin music and Michelin desserts add a special touch during exclusive events.

People are saying

"The Italian food, especially the pasta, is amazing."

"The speakeasy bar downstairs was amazing."

"I enjoyed live jazz downstairs after dinner."

Good to know

1

Reservations are advisable to ensure the best service and seating.

2

The Valentine's Day event starts at 8pm in the 'red room'.

3

Expect the event to be crowded; arrive early to secure your spot.

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