5 Best Cabarets in Chicago (2026)

Independently ranked by our review of ratings, reviews and reputation · How we chose

By Thorne Savarin, Culinary Explorer · ✓ Data verified July 2026 · 7 min read

A night out at a Chicago cabaret can mean dueling pianos, a drag brunch, or 27 floors up with a DJ and skyline views, and these venues have pulled in over 11,500 Google reviews between them. Ratings run from 4.2 to 4.7, so the gap between the top and bottom pick here is wider than on most of our lists, and it tracks pretty closely with how much of the night is show versus scene.

Short answer: Howl at the Moon Chicago draws the most reviews of any cabaret-style venue in the city at 4.4 stars across nearly 3,825 Google reviews, built around its dueling piano show. Lips Drag Queen Show Palace posts the highest rating at 4.7 for its nightly drag dinner shows, and expect a cover charge of roughly $10 to 20 on top of food and drinks at most of these spots.

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1. Howl at the Moon Chica…
2. Flight Club Chicago
3. Lips Drag Queen Show P…
4. Brando's Speakeasy
5. ROOF on theWit
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Chicago's Cabarets and Dinner Shows Compared

#	Business	Rating	Reviews	Best for
1	Howl at the Moon Chicago	4.4 ★	3,821	Overall / most reviewed	View ›
2	Flight Club Chicago	4.6 ★	1,956	Interactive / groups	View ›
3	Lips Drag Queen Show Palace, Restaurant & Bar	4.7 ★	1,369	Highest rated / drag show	View ›
4	Brando's Speakeasy	4.3 ★	2,171	Karaoke	View ›
5	ROOF on theWit	4.2 ★	2,278	Rooftop views	View ›

Our top picks, reviewed

#1 Overall🕑 Open 7 days↩ Responds to reviews

Howl at the Moon Chicago

4.43,821 Google reviews

Howl at the Moon Chicago is a dueling piano bar on Hubbard Street where a rotating cast of musicians plays requests across piano, drums, and guitar, taking song suggestions straight from the crowd. It draws the most reviews of any cabaret-style venue in the city and runs nightly shows with a cover charge, staying open past midnight most nights.

What people praise

Musicians praised repeatedly for talent across multiple instruments and vocals
High-energy, crowd-driven show that builds through the night
Good for groups, birthdays, and bachelorette parties
Open late every night of the week

Worth knowing

Kitchen may be closed by the time you arrive late in the evening
Skews toward a younger crowd on weekend nights

Reputation scorecardrank in Chicago

Rating4.4 / 5

Review volume3,821 · 98th

Confidencevery high

Recency3 weeks ago

Info completenesssite · phone · hours

Rating breakdown66% 5-star

✓ VerifiedSource: Google

Our take: The most-reviewed cabaret-style night out in Chicago, and reviewers who go in skeptical tend to come out won over. A safe pick for a group looking for a fun, loud night.

Website +1312-863-7427 Directions

26 W Hubbard St, Chicago, IL 60654

#2🕑 Open 7 days↩ Responds to reviews

Flight Club Chicago

4.61,956 Google reviews

Flight Club Chicago on Wacker Drive combines a full food and cocktail menu with tech-enabled Social Darts in semi-private booths, part of a UK-founded chain with locations across the US and UK. It leans upscale-pub rather than traditional cabaret, with games and a DJ-driven atmosphere built for groups.

What people praise

Interactive dart games with instant scoring keep groups engaged
Flatbread and smash burger draw consistent praise
Staff accommodate special requests like birthday setups
Semi-private booths work well for celebrations

Worth knowing

Portion sizes on some shared plates run smaller than expected

Reputation scorecardrank in Chicago

Rating4.6 / 5

Review volume1,956 · 83th

Confidencevery high

Recency2 months ago

Info completenesssite · phone · hours

Rating breakdown75% 5-star

✓ VerifiedSource: Google

Our take: Less a traditional cabaret and more an interactive night out, best for a group that wants games alongside food and drinks rather than a stage show.

Website +1312-284-2474 Directions

111 W Wacker Dr, Chicago, IL 60601

#3🕑 Open 5 days/wk

Lips Drag Queen Show Palace, Restaurant & Bar

4.71,369 Google reviews

Lips Drag Queen Show Palace, Restaurant & Bar on Michigan Avenue has run nightly drag dinner shows for over 25 years, including a Sunday drag gospel brunch with bottomless mimosas. The menu covers steak, salmon, and lobster ravioli alongside the performances, and it holds the highest rating on this list.

What people praise

Highest rating on the list at 4.7
Performers singled out by name for energy and audience interaction
Inclusive, high-energy atmosphere without explicit content
Sunday brunch show is a popular standalone draw

Worth knowing

Reviewers suggest confirming exactly what's included before booking
Food gets mixed marks, most reviewers are there for the show first

Reputation scorecardrank in Chicago

Rating4.7 / 5

Review volume1,369 · 78th

Confidencevery high

Recency2 months ago

Info completenesssite · phone · hours

Rating breakdown82% 5-star

✓ VerifiedSource: Google

Our take: The top-rated pick here, and the drag show itself is clearly the draw over the dinner menu. Go in knowing you're there for the performance.

Website +1312-815-2662 Directions

2229 S Michigan Ave, Chicago, IL 60616

#4🕑 Open 7 days

Brando's Speakeasy

4.32,171 Google reviews

Brando's Speakeasy in the Loop has run as Chicago's karaoke and cocktail lounge since 2007, with a song library of over 300,000 tracks and private rooms available for larger groups. It's built as a vintage-style tavern rather than a stage show venue, with a second location in Lincoln Park.

What people praise

Massive song library covering multiple languages and eras
Regulars describe a welcoming, diverse crowd across age groups
Bartenders offer solid recommendations when a specific drink isn't in stock
Private rooms available for company parties

Worth knowing

One reviewer described a last-minute booking cancellation when a larger group rebooked the venue, worth confirming reservation terms for large events
Weekend nights can get loud and crowded

Reputation scorecardrank in Chicago

Rating4.3 / 5

Review volume2,171 · 88th

Confidencehigh

Recency2 months ago

Info completenesssite · phone · hours

Rating breakdown60% 5-star

✓ VerifiedSource: Google

Our take: The pick if karaoke is the point rather than a hosted show. Confirm reservation details directly with the venue if you're planning a group event.

Website Book now +1872-327-3334 Directions

343 S Dearborn St, Chicago, IL 60604

#5🕑 Open 7 days↩ Responds to reviews

ROOF on theWit

4.22,278 Google reviews

ROOF on theWit is a rooftop bar and lounge 27 stories above downtown Chicago, combining a DJ, floor-to-ceiling skyline views, and a food menu that includes lobster tacos and bao buns. It has been recognized in travel media for its views and runs nightlife events alongside its regular dinner and drink service.

What people praise

Bao buns and small plates get consistent praise
Panoramic skyline views from the 27th floor
Attentive service even during large events
Retractable roof keeps it open year-round

Worth knowing

Music volume can run loud enough to make conversation difficult
Pricing sits at the higher end of this list

Reputation scorecardrank in Chicago

Rating4.2 / 5

Review volume2,278 · 93th

Confidencehigh

Recency8 weeks ago

Info completenesssite · phone · hours

Rating breakdown61% 5-star

✓ VerifiedSource: Google

Our take: The lowest rating on this list, but the views and DJ-driven atmosphere are the draw, not a traditional show. Go for the skyline, not a quiet dinner.

Website +1312-239-9502 Directions

201 N State St 27th Floor, Chicago, IL 60601

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How we score

Every number on this page comes from public Google data on the date shown, not opinion or payment. Rating is the venue’s live Google star average. Review volume is how many customers have rated them, ranked against other Chicago cabarets and dinner-show venues. Confidence weighs the rating by that volume, so a 4.4 from thousands of reviewers carries more weight than a 4.7 from a few hundred. Recency reflects how recently people are still leaving reviews. No business can pay to change these numbers.

How much does a cabaret night out cost in Chicago? (2026)

Pricing depends heavily on the venue, and on whether the night is built around a show, a full dinner, or just drinks. Reviewers on this page most often reported per-person spend between $20 and 70, with rooftop and dinner-show venues running toward the higher end once food and a cover are added in.

Serving all of Chicago

These venues cluster around downtown Chicago and the Loop, from Hubbard Street and Wacker Drive to Michigan Avenue and State Street. Searching for a cabaret or dinner show near me? Every listing below shows a live phone number and address so you can find the closest option fast.

What to ask before you book a Chicago cabaret or dinner show

Is there a cover charge, and does it change on weekends?
Do you take reservations for groups, and what’s your cancellation policy?
Is the food menu full-service or limited during the show?
What time do doors open versus when the show starts?
Is there an age minimum or dress code?

Frequently asked questions

How did you choose these cabarets and dinner shows?

We started from cabaret and dinner-show venues in Chicago with a public Google presence, then ranked by rating, review volume, consistency, and recency. See How we score above.

Are these rankings paid?

No. Rankings come from the public Google data in the scorecard. A business can pay to be a Featured Partner, which adds a badge and top placement, but that never changes another business’s score or position on the underlying data.

How often is this updated?

The data carries a verified date (July 2026 on this page). We refresh listings periodically so ratings and review counts stay current.

Which venue is best for a bachelorette party?

Howl at the Moon and Lips Drag Queen Show Palace both run regular bachelorette bookings, with dueling pianos at one and a nightly drag show at the other.

Is there a rooftop option on this list?

Yes. ROOF on theWit sits 27 stories up with skyline views, a DJ, and a food menu, though it leans more nightlife lounge than traditional cabaret.

The bottom line

Howl at the Moon is the safe default with the deepest review base and a show built to get a crowd involved, while Lips is worth the trip if a drag dinner show is exactly what you’re after. Book ahead for weekend nights either way.

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