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Chicago's best

Desserts and live music

A dessert you can actually hear yourself think over while the live music plays in the background.

Based on 776 Opinions
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Updated June 2026
01
Velour Restaurant image 1
Velour Restaurant image 2
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Elegant space combines stylish design with a cozy atmosphere and live music that energizes evenings. Guests enjoy a warm, inviting vibe with attention to detail in decor and presentation. Seating can feel heavy, but the overall environment supports both intimate dinners and celebrations.

Desserts here are delicate and elegant with impeccable taste. They stand out as a highlight, bursting with flavor and highly recommended to try.

Saturday nights feature live music that creates a festive atmosphere for dates and celebrations. Performances often include an excellent lady singer adding a special touch.

People are saying

"The food here feels like love, peace, and human dignity."

"The desserts here are edible art, almost too pretty to eat."

"The live music here creates a wonderful atmosphere."

Good to know

1

Reservations are recommended for events to ensure availability.

2

Expect a 21% service charge automatically added to your bill.

3

The restaurant is suitable for hosting events like weddings and family gatherings.

02
Madame Puffs and Thai Bistro image 1

Modern, chic dining space features luxurious decorations and bright golden lettering outside. Live jazz music creates a warm, inviting atmosphere that complements the upscale Thai cuisine. The small, intimate layout brings diners close to servers, enhancing the lively vibe.

Pineapple crispy crusted puff stands out as a dessert option. Meals often include a free dessert, and special occasions get a complimentary birthday dessert.

Live jazz music creates a warm, inviting atmosphere that enhances the evening. A versatile singer performs various musical genres, adding to the fun experience.

People are saying

"The food here is amazing and full of flavor."

"This place is perfect for dates with its warm, intimate atmosphere."

"You've got to try the desserts, especially the crispy crusted puff."

Good to know

1

Reservations are recommended, especially on weekends to avoid long wait times.

2

The restaurant is BYOB, so bring your favorite drink.

3

Expect a separate charge for protein in dishes, which can increase total costs.

03
Vincent image 1
American restaurant

Small space with chic interior and patio adorned with planters creates a cozy, romantic vibe. Live entertainment features top-notch musicians and comedians, making the atmosphere lively but sometimes loud. Craft cocktails and select dishes stand out amid a stylish, intimate setting.

Three desserts and cocktails deliver fantastic flavors. Every bite proves worth it, even after a full meal.

Live music features piano performances and acts like Molly & Alex and Amy Armstrong. Shows have no cover charge and create a casual, sing-along vibe.

People are saying

"Kenny makes the most delectable cocktails."

"I loved the live music, especially the piano."

"The chocolate mousse dessert was light, airy, and not cloyingly sweet."

Good to know

1

Happy hour is available seven days a week with special cocktail deals.

2

Live music occurs on Tuesdays featuring an electric baby grand.

3

There is no cover charge for live music events.

04
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.

Dinner finishes with an île flottante, a light and unexpected dessert. Desserts stand out alongside dishes like escargot and steak tartare.

Live jazz fills the space with the Daniel Chavez Trio performing on Wednesday nights. The music creates a vibrant atmosphere that draws attention.

People are saying

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

"The desserts here are classic, including French toast and gelato."

"The live music here creates a great ambiance."

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.

05
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.

Tortoise pie stands out as a dessert option. Other desserts come highly recommended and pair well with appetizers and drinks.

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 desserts here are outstanding, especially the cherry pie."

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.

06
Coq d'Or image 1
Restaurant

Classic bar and restaurant with an old-school charm and 1930s cozy atmosphere featuring live piano and jazz performances. The space feels dark and crowded, often lively with music and sports on TVs. It attracts a mix of guests seeking a timeless, elegant vibe with a touch of history.

Desserts include a banana mussoline and a ginormous cheesecake. These options stand out after meals.

Live jazz music plays on Friday and Saturday nights, adding to the laid back and cozy 1930s atmosphere. A live piano player performs sing-along songs, creating a vibe like a dueling piano bar.

People are saying

"It's a cozy spot with a nice, quiet atmosphere."

"The live music here creates such a warm and cozy atmosphere."

"I had the most rich, delicious cheesecake for dessert."

Good to know

1

Live jazz music is offered on Friday and Saturday nights.

2

Reservations are recommended during busy holiday seasons.

3

Expect higher prices due to the restaurant's location in a hotel.

07
Chicago Chop House image 1

Restored brownstone with early 1900s decor and photos of local celebrities creates a traditional steakhouse atmosphere. Live piano music plays softly, adding to the luxurious and old-fashioned vibe. Comfortable seating and personalized touches enhance a refined dining experience.

House-made desserts stand out with a spectacular quality. They complement the menu well and show a sense of value and appreciation for guests.

Live piano music plays throughout, creating a cozy and inviting atmosphere. The setting blends an old-school steakhouse vibe with a historic ambiance.

People are saying

"I found the steak to be tender and flavorful."

"The desserts here are tender and flavorful."

"The live piano music really added to the charming atmosphere."

Good to know

1

During the 40th anniversary, all food ordered was 40% off.

2

Valentine’s Day celebrations offer special menu items.

3

Reservations are recommended, especially during holidays.

08
Vito’s Vault image 1
Dinner theater

Dinner theater recreates 1929 speakeasy with interactive comedy and live music. Atmosphere blends Old School Chicago charm and prohibition-era decor with engaging performances. Crowd participation and multi-talented cast create a lively, immersive experience.

Desserts come during the intermission of a three-course meal. They are consistently delicious and provide a sweet finish to the dining experience.

Live piano music and live singers create a strong presence that often outshines other aspects. Performances include song, dance, and comedy, offering a joyful break from daily life.

People are saying

"I thought the food here was delicious and tasty."

"The show's hilarious characters made the whole experience feel unique."

"The food and drinks were delish, and the live music was entertaining."

Good to know

1

The $80 ticket includes a 4-course meal and a 90-minute interactive show.

2

Parking is plentiful and easy near the venue.

3

The performers serve meals, creating a unique dining experience.

09
Turquoise Cafe & Restaurant image 1
Mediterranean restaurant

Mediterranean restaurant offers spacious outdoor patio with live jazz music creating a warm and inviting atmosphere. The setting suits casual sit-down meals with a vibrant, welcoming vibe. Seating options include a cozy back room and beautiful sidewalk dining.

Servers often offer complimentary desserts like tiramisu or birthday treats with candles. Desserts come across as delectable and sometimes special for celebrations.

Live piano music sets a great ambience inside. Outdoor seating features live jazz music for a relaxed sidewalk dining vibe.

People are saying

"The food here is delicious and satisfying."

"The desserts here are so good, especially when Furkan recommends them."

"The live piano music here creates a great ambience."

Good to know

1

Happy hour runs daily with special discounts on drinks and appetizers.

2

Live music is featured every Saturday evening, creating a lively atmosphere.

3

Daily specials are available, offering unique dishes each day of the week.

10
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.

Signature butter cake stands out as a highlight. Personalized menus and birthday desserts with candles add a special touch to celebrations.

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."

"You have to try the butter cake; it's a must-try."

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.

11
The Soul Food Lounge image 1
American restaurant

Small, contemporary space combines live jazz saxophone with beautiful decor to create an inviting atmosphere. The vibe feels intimate and soulful, drawing a crowd that appreciates well-crafted soul food and a relaxed setting.

The dessert menu features a grilled pound cake that stands out for its rich flavor. A tasting option includes three entrees paired with wine or dessert at a reasonable price.

Live jazz music fills the space with amazing performances. A functional kitchen and inviting dining room sit alongside the music, creating a cozy atmosphere.

People are saying

"The American Food here is phenomenal, especially the perfectly seasoned yams."

"I loved the Creole Seafood Dressing; it was very good."

"You can't skip the desserts; the grilled pound cake is warm and buttery."

Good to know

1

Restaurant Week 2024 offers a $59 deal for three entrees of your choice.

2

The lounge does not serve liquor, but customers can BYOB with a corkage fee.

3

Reservations are recommended, but tables are often available without one.

12
Gale Street Inn Chicago image 1

Newly remodeled space combines Great Gatsby decor with a supper club vibe and a small stage for live jazz and ukulele performances. Atmosphere feels cozy and inviting with ample table spacing for comfortable conversation. Lively evenings feature phenomenal live music that enhances the classic old school Chicago environment.

Chocolate cake stands out as a favorite dessert. Drinks and desserts both deliver really good flavors. Overall, desserts are exceptional alongside other dishes.

People are saying

"These ribs are the best in town, truly fall-off-the-bone perfection."

"The live music here is incredible, just like the ribs."

"The live music here really adds to the cool vibes."

Good to know

1

Reservations are recommended because the place fills up quickly.

2

Live jazz music happens on Thursday, Friday, and Saturday nights.

3

The free parking is convenient.

13
El Nandú Restaurant image 1
Argentinian restaurant

Argentinian restaurant with cozy, artsy decor and live music featuring tango and salsa on weekends. Atmosphere stays quiet and warm, ideal for couples dinners. Known for authentic churrasco and empanadas, it offers a romantic, welcoming vibe.

Desserts come with fair prices and tasty flavors. A free gift dessert is offered on the first visit, and ordering dessert is recommended.

Live music features a variety of styles like tango, Chilean cuecas, and Ecuadorian salsa. Performances by groups such as Trio Los Primos happen regularly, especially on weekends.

People are saying

"I found the empanadas crispy, fresh, and delicious."

"The steak here is delicious and tender."

"The desserts here are delicious and fairly priced."

Good to know

1

Live music happens every Thursday night at El Nandú Restaurant.

2

The restaurant is family-owned and has been operating for 34 years.

3

Expect medium to high pricing for meals, especially steak dishes.

14
The SoulFood Lounge 2 image 1
Soul food restaurant

Small soul food restaurant offers an intimate atmosphere with an all-black aesthetic and live music featuring jazz and saxophone. The vibe stays laid back and refreshing, suited for quiet dinners or date nights. Space is limited, creating a cozy but sometimes cramped setting.

Desserts come with the Grand Tasting, which includes three entree samples and a choice of wine or lemonade. The dessert options are part of a generous meal that often exceeds expectations and are described as fresh-made and amazing.

Intimate lounge offers clear sound where live music blends with good service and tasty food. The setting supports conversation and enjoyment of the black owned vibe.

People are saying

"The American Food here, like the turkey leg, is off the bone and delicious."

"The food here is excellent and generously portioned."

"You have to try the grilled pound cake for dessert; it's perfect."

Good to know

1

Reservations are necessary to secure a spot inside the restaurant.

2

Parking can be difficult, often requiring a walk from 1-3 blocks away.

3

The restaurant has a 'No Share Policy' for events like 'The Grand Tasting'.

15
The 101 Bar, Grill & Rooftop image 1
Mediterranean restaurant

Mediterranean restaurant with a rooftop bar offering spectacular city views and multiple seating options including fire pits and private couches. Live music creates a lively atmosphere that balances well with conversation. Cocktails and food receive strong praise, contributing to an overall vibrant and welcoming vibe.

Thoughtful dessert boards feature candled-top sweets that light up with a fireworks show. Generous portions make the experience memorable and the quality stays consistently top notch.

A live Jazz trio plays on the terrace, creating a fantastic ambiance that blends well with the setting. The music adds to the atmosphere without overpowering conversation.

People are saying

"The rooftop views of the city are beautiful."

"The live jazz trio really added to the lovely evening."

"The desserts here are a dazzling fireworks show!"

Good to know

1

Happy hour is available 7 days a week from 5-7pm.

2

Reservations are typically required, but walk-ins may be accommodated if available.

3

The happy hour offers a great selection of drinks and appetizers at unbeatable prices.

16
Chief O'Neill's Pub Restaurant Beer Garden image 1

Beer garden features twinkling string lights and lush greenery, creating an enchanting atmosphere with an authentic Irish pub feel. Large covered patio hosts live traditional music and special events, adding to the festive vibe. The space balances festive decorations with a cozy, lively energy.

Endless dessert options fill the buffet, including cannolis and a bread pudding topped with ice cream, chocolate, and caramel sauce. The dessert spread stands out as a sweet ending to the meal.

Traditional live music plays regularly, creating a lively atmosphere. Nights with music stand out, often paired with festive decorations and a setting suited for parties.

People are saying

"The food here is delicious and fantastic."

"I loved the traditional live music and festive atmosphere here."

"The dessert spread here has so many options, especially the cannolis."

Good to know

1

The Sunday brunch buffet is all-you-can-eat for $32.

2

Reservations are recommended for the Sunday brunch due to high demand.

3

Live Irish music is featured on Sundays from 5-7 PM.

17
Grill on 21 image 1
Restaurant

Restaurant occupies a sleek, upscale space on the 21st floor with an art deco and speakeasy vibe. Ambient live jazz music plays softly, creating a lively yet inviting atmosphere. Booths accommodate small groups comfortably, enhancing the overall elegant dining experience.

Desserts include tiramisu and carrot cake. Wine pairs well with the sweet options. Simple ice cream choices are not available.

Live music features a live jazz band that plays softly, adding to the atmosphere without overwhelming it. The style leans toward Renaissance, creating a lovely and pleasant backdrop for dining.

People are saying

"The food here tasted lovely and was outstanding."

"The live jazz here is a wonderful addition to the atmosphere."

"The desserts here are good, especially the carrot cake."

Good to know

1

Live jazz performances happen every Friday and Saturday evening.

2

A 20% gratuity is automatically added to bills for parties of two.

3

Sourdough bread is often out of stock, so consider alternatives.

18
Nuevo Leon Restaurant image 1
Mexican restaurant

Mural-covered walls and pueblo-themed decor create a vivid setting that feels like stepping into Mexico City. Live ranchera music fills the space, adding to a lively atmosphere with comfortable seating throughout. The place draws people looking for authentic Mexican food paired with classic drinks like Micheladas and Margaritas.

Creamy rice pudding often comes as a small, complimentary dessert. It serves as a smooth, sweet finish to the meal.

Live music happens on weekends, usually Saturdays from 2 to 6 pm, featuring good singers. The singers are amazing, and people can join in and belt their heart out during the sessions.

People are saying

"I found the Mexican food here to be delicious and authentic."

"They brought out a little rice pudding dessert, which was delicious."

"The live music here was enjoyable and the singers were amazing."

Good to know

1

Karaoke happens on weekends, providing a fun atmosphere.

2

Live music is featured on Saturdays from 2 to 6 pm.

3

The restaurant accepts cash only for all transactions.

19
the Albert image 1
American restaurant

Space combines vintage scholarly decor with modern touches and thousands of old books. Atmosphere feels vibrant and lively with live music from guitar duos or three-piece bands enhancing the mood. Guests enjoy outdoor seating and a full bar offering standout cocktails like the Smokey Old Fashioned.

Surprise desserts often mark special occasions here, adding a personal touch. The kitchen offers complimentary desserts alongside drinks or appetizers, enhancing the dining experience.

Wednesdays feature live jazz music that creates a magical ambience. The bands add a great touch to the atmosphere.

People are saying

"The dinner spots here are seriously so good and delicious."

"The Italian-style brunchissimo experience felt like the soul of Southern Italy."

"The live music really adds a magical touch to the atmosphere."

Good to know

1

Wednesdays feature live music, enhancing the dining experience.

2

Unlimited mimosas for two hours at $26 are available during brunch.

3

Happy hour offers three daily bar specials, perfect for budget-friendly drinks.

20
Chemistry Chicago image 1

Restaurant features live music and staff in lab coats creating a chemistry-themed atmosphere with stylish decor. Energy runs high with a loud, chaotic vibe and a crowded space. Food includes standout dishes like wagyu fettuccine and lamb chops, while cocktails are notably overpriced.

Desserts come with a rich selection and are part of a menu that pairs well with drinks and lamb chops. The vibe includes live music and a playlist that complements the delicious dessert offerings.

Live music features a live band and singer alongside a DJ, creating a vibrant atmosphere. Jazz performances add to the energy, making even Monday nights feel like weekends.

People are saying

"The food here is amazing and delicious."

"The live band here was amazing and on point."

"You have to try the butter cake; it's warm and rich."

Good to know

1

Sunday brunch ends at 3:00 PM, so arrive early.

2

A 20% gratuity and a 5% entertainment fee are automatically added to bills.

3

Reservations are for 1.5 hours, so plan accordingly.

21
Palm Court image 1
Restaurant

Elegant decor centers around a large fountain, creating a grand atmosphere enhanced by a live harpist playing throughout. The space feels overcrowded with tightly packed tables, contributing to a bustling energy. Guests often add champagne to their tea, complementing the refined setting.

Small desserts come out alongside the meal, sometimes as a special treat for occasions like a bachelorette party. These great, bite-sized sweets complement the light sandwiches and scones well.

Beautiful live music fills the space, creating a beautiful atmosphere that enhances the experience. Music plays during visits, adding a lively touch.

People are saying

"The tea options are incredible, with delicious cakes and crumpets."

"The desserts here are prompt and attentive."

"The live music here is beautiful."

Good to know

1

High Tea is available year-round at Palm Court.

2

The Holiday Tea experience costs $77 per person.

3

Reservations are recommended for the High Tea service.

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