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Cocktails and performing arts

A night at the theater that includes a real cocktail instead of a watered-down drink in a plastic cup.

Based on 727 Opinions
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Updated May 2026
01
Greenhouse Theater Center image 1
Greenhouse Theater Center image 2
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Performing arts theater

Small performing arts theater offers an intimate seating arrangement and excellent acoustics that create a cozy, immersive atmosphere. Performances feature expressive, committed actors and strong talent, appealing to both adults and young audiences. Two bars, including one inside the theater space, add to the welcoming vibe.

Brilliant cocktails flow smoothly and keep a light buzz through the show. Drinks go down easily and taste pretty great.

Intimate theater setting creates a close connection with actors and performances. Offers a mix of community theater, kids programs, and adult shows with drinks, making it a versatile spot for live performing arts.

People are saying

"I found the children's theater performances to be a delight."

"I loved the Edgar Allan Poe Speakeasy and its spooky actors."

"I drank pretty great cocktails here."

Good to know

1

Parking is free on Sundays, which is rare for Chicago.

2

The theater validates parking, but the discount is only $8.

3

Buying tickets online is quick and easy, with free will call pickup.

02
The Rhapsody Theater image 1
Theater production

Small venue with intimate cabaret seating and a beautiful, recently renovated space creates a marvelous and mysterious atmosphere. Shows feature engaging magic performances with excellent sightlines and sound, making it a cozy spot for close-up entertainment.

Classy cocktails and wonderful zero-proof options stand out here. The menu includes mocktails and even a kiddie cocktail for younger guests.

Intimate setting with great sightlines, sound, and lighting makes it ideal for magic shows. The venue includes a beautiful theater, lobby, and bar, creating a complete performing arts experience.

People are saying

"I found the theater beautiful and nicely appointed."

"The magic shows here are so fun and made everyone laugh."

"The cocktails and mocktails here are excellent."

Good to know

1

Valet parking and metered street parking are available near the theater's entrance.

2

Drinks and appetizers are available during the show.

3

The show lasts about two hours, including 30 minutes of magic.

03
Winter's Jazz Club image 1

Small, intimate jazz club with phenomenal acoustics and a speakeasy atmosphere. Live performances happen up close, creating a relaxed and welcoming vibe. Cocktails stand out as among the best, complementing the music well.

Cocktails here are consistently excellent and very good, with the bartender crafting delightful drinks including non-alcoholic options that stand out for their flavor.

Live shows feature talented musical acts often playing jazz with a mix of contemporary and avant garde styles. Artists engage with fans after performances, signing autographs and creating a friendly atmosphere.

People are saying

"It's a beautiful, intimate room for enjoying jazz."

"The cocktails here are amazing and refreshing."

"I loved the jazz performances, especially the standards."

Good to know

1

Tickets can be purchased online, with VIP seating available for $40.

2

Winter's Jazz Club does not serve food or snacks.

3

Getting to the club can be somewhat hidden and may require some effort.

04
Drunk Shakespeare Chicago image 1
Performing arts theater

Small, intimate theater with benches opposite each other and bookshelves on all walls creates a cozy, engaging space. Performers deliver high-energy, hilarious Shakespearean plays while interacting closely with the audience. Drinks and food arrive at seats via QR code ordering, enhancing the relaxed, lively atmosphere.

Signature cocktail features homemade lemonade, makers, and blackberry liqueur. Drinks come with a welcome shot and pair well with snacks like caviar.

Offers a fun adult experience with a fairly good recreation of Billy's play. Presents a memorable version of the Scottish play that stands out among theater performances.

People are saying

"It's hilariously fun and unpredictable."

"The performing arts here are hilarious and a great time."

"The cocktails were delicious, especially the welcome shot."

Good to know

1

Must be 21 to enter; ID checked for all ages at the door.

2

The show is rated R and not suitable for the faint of modesty.

3

Expect a fun and unique experience with a comedic twist on Shakespeare.

05
Theater Wit image 1
Performing arts theater

Small venue with intimate seating and comfortable chairs creates a close connection to performances. Engaged audiences foster lively interaction, while a full bar offers drinks inside the theater. The space supports bold, emotionally honest shows that stand out for their quality and spirit.

Strong, well-mixed cocktails come from the bar inside the theater. Drinks lean toward the high strength side and carry a pricey tag, often requiring sharing to finish.

Performances blend bold, smart programming with intimate settings across three smaller theaters. Shows range from emotionally honest dramas to comedic and musical pieces that engage the audience deeply.

People are saying

"The intimate performing arts venue makes you feel part of the show."

"The seating is intimate and comfortable, so you feel part of the show."

"I had some good cocktails from the bar before the show."

Good to know

1

Tickets are usually priced around $35 for shows.

2

Seats at Theater Wit are not assigned, so arrive early for the best choice.

3

The theater has a board displaying current and upcoming events.

06
Carol's Pub image 1

Classic honky-tonk bar with live country music and a lively atmosphere that balances energy without overwhelming. Small venue with up-close concert feel and generous, tasty food like cheeseburgers and fries. Crowd enjoys affordable drinks and a neighborhood vibe with artsy, charming decor.

Excellent cocktails and signature drinks keep the group happy. Reasonable daily specials on beer and cocktails add value.

Live music features Patrick Bale and the Pale Ales with an awesome band. The venue also hosts live country music and trivia nights.

People are saying

"I loved the live music and the lively crowd."

"I thought the burgers here were pretty good for the price."

"The atmosphere here is so unique and artsy, it's a blast!"

Good to know

1

Karaoke events happen on Thursdays with a two-drink minimum.

2

Trivia night is every Wednesday at 8pm with no entry fee.

3

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

07
Epiphany Center for the Arts image 1

Historic church converted into an event venue offers intimate acoustics and rotating art displays. The atmosphere blends inviting neighborhood vibe with diverse live music, including jazz and DJ sets. Outdoor terrace and garden spaces complement the indoor bar and dance floor areas.

Cocktails here come with a fresh twist and are part of a terrific lineup alongside food and entertainment. The drinks lean toward the very expensive side but match the warm vibe of live music shows.

A large event space hosts high-quality musicals like The Obama Musical, delivering performances on par with NYC Broadway. Shows celebrate musical talent and cultural diversity.

People are saying

"I found the renovated church space really cool and artsy."

"I found the cocktails here to be fresh and perfectly balanced."

"The performing arts here celebrate Black voices and local talent."

Good to know

1

Happy hour runs from 4-7pm in the main bar with discounted drinks.

2

Free or low-cost events are available all weekend long.

3

Parking is limited; nearby street and garage options are available.

08
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.

Jazz and great cocktails come together here. The cocktail menu offers excellent choices, though it lacks a signature house cocktail.

Flawless acoustics highlight every musical nuance during performances. The Vibraphonist Thaddeus Tukes Quintet delivers beautiful music, with Keyon Harold's trumpet showcasing clear musical genius.

People are saying

"I enjoyed the great live jazz performances here."

"I enjoyed the excellent cocktails and draft beers."

"The jazz performing arts here transport you to its golden age."

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.

09
Thalia Hall image 1
Live music venue

Historic opera house converted into a modern music venue offers intimate concerts with great acoustics and vintage architecture. Spacious layout includes a balcony and multiple bars, creating a cool atmosphere with excellent views from all angles.

Two bars upstairs serve cocktails, beer, wine, and spirits with reasonably priced draft cocktails that taste decent. The basement hosts a juice-based cocktail bar called The Punch Bowl and offers a variety of N/A specialty cocktails that are well balanced.

A historic theater with a beautiful old design hosts multiple musical acts with smooth transitions between performances. The theater and lounge offer a great setting for shows.

People are saying

"It's an intimate venue with awesome sound and good acoustics."

"The cocktails here are great and the sound quality is lovely."

"I found the theater to be beautiful and amazing."

Good to know

1

Parking in the area can be rough; add time for street parking.

2

The coat check costs $5.

3

Food is reasonably priced, with popcorn at $4 and hot dogs at $5.

10
Ramova Theatre image 1
Live music venue

Historic theater space combines intimate atmosphere with top-notch acoustics and stylish, hip design. The venue offers an attached bar and grill with standout cocktails and comfort food, creating a lively yet cozy setting for live music events.

Multiple bars serve well-balanced specialty cocktails on draft with quick, friendly staff. The front bar offers different cocktails than inside, but all mixed drinks come from canned bottles poured into plastic cups.

Stunning art deco architecture sets a classic tone for every show. The theater offers amazing sound quality and every seat provides a great view of the stage.

People are saying

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

"The staff at this performing arts venue were so friendly and respectful."

"The specialty cocktails on draft were well-balanced and the staff was friendly."

Good to know

1

The Ramova Theatre is wheelchair accessible.

2

Ticket prices are reasonable.

3

Parking is a few blocks away, which can be inconvenient.

11
Howl at the Moon Chicago image 1

Rocking piano bar with live music and high energy atmosphere. Crowded seating near the stage creates an intimate vibe while the buzzing sound level keeps the energy lively. Specialty drinks come with sweet, cutesy presentations and the food offers elevated bar fare.

Cocktails come in creative options and are delicious. Drinks sometimes arrive in buckets, adding a unique touch.

Musicians here show incredible versatility, playing every instrument and switching roles during songs. Performances feature amazing singing and cover a wide range of genres with ease.

People are saying

"You'll have so much fun; the crowd is always energized."

"The live music here is incredible, with talented musicians playing every instrument."

"The live music here is incredible and the atmosphere is great."

Good to know

1

There is a $12 cover charge to enter the venue.

2

Happy hour offers the first two drinks for $2 each.

3

Dueling piano nights are popular and feature audience requests.

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