Best Live Music Restaurants in Old Town

79 restaurants available nearby

1. Kayao

4.6

Exceptional(130)

Price: Expensive

• Peruvian • Old Town

Booked 15 times today

At Kayao, we aim to showcase the dynamic flavors, techniques, and ingredients that unite Peruvian and Asian culinary traditions. Kayao is a melting pot of cultures and cuisines, where guests are invited to embark on a culinary journey that transcends borders and opens hearts. Through our commitment to authenticity, creativity, Kayao seeks to create intrigue while also pushing the boundaries of culinary innovation.

2. Andy's Jazz Club

4.7

Exceptional(5005)

Price: Moderate

• Contemporary American • River North (Chicago)

Booked 57 times today

Admission is charged to all guests entering the venue and goes toward the musical entertainment that all will be enjoying while inside the club. All dining tables are good for 1 musical performance only. Please choose your reservation time according to your desired performance time. Andy's Jazz Club is a unique as a Jazz Room that offers full dining. We hope for a quiet room during all performances. We do ask that all guests be courteous to the artists while performing and keep conversation volume down during shows.

3. The Palm Court

4.7

Exceptional(4843)

Price: Very Expensive

• Afternoon Tea • Gold Coast / Streeterville

Booked 120 times today

For those who love their afternoon teas fresh, fragrant and steeped in history, Palm Court at The Drake Hotel serving tea for over a century. Even the Queen and Princess Diana have made their royal visits here. Your afternoon tea begins with Palais de Thes menu, which features 15 tea blends including classic selections like the English Breakfast to modern yet delightful twists like the Mélange du Cap.Tea is served in individual tea pots accompanied by the traditional three tiered tea tray filled with an arrangement of gourmet finger sandwiches and scones; and dainty petit fours with complements of preserves, lemon curd and English double Devon cream.And let’s not forget about our little tea. The Prince & Princess Afternoon tea service, suitable for children between 3 and 12 years of age is available throughout the duration of afternoon tea service.Reservations are heavily encouraged. Tea service seating duration is 90minAdults $79/ $82 with Carolers / Kids $35 (3-12)

A photo of Mastro's Steakhouse - Chicago restaurant

4. Mastro's Steakhouse - Chicago

4.7

Exceptional(6320)

Price: Expensive

• Steakhouse • River North (Chicago)

Booked 43 times today

Mastro's collection of sophisticated, classic Steakhouses and Ocean Club seafood locations are recognized for their combination of world-class service, highly acclaimed cuisine, and live entertainment in an elegant yet energetic atmosphere. A truly unparalleled dining experience.

A photo of Gibsons Bar & Steakhouse - Chicago restaurant

5. Gibsons Bar & Steakhouse - Chicago

4.7

Exceptional(8834)

Price: Expensive

• Steakhouse • Gold Coast / Streeterville

Booked 123 times today

Gibsons Bar & Steakhouse has been a Chicago icon since partners Hugo Ralli and Steve Lombardo opened its doors in May 1989. The classic American steakhouse serves Gibsons Prime Angus Beef and Gibsons Grassfed Australian Beef. Gibsons also features fresh fish, classic cocktails, an extensive wine list and exceptional service. Celebrities, Chicago visitors and loyal neighborhood residents enjoy three distinct locations: Chicago, Rosemont and Oak Brook. Beautiful private dining and events spaces available.

6. Adalina

4.5

Awesome(2311)

Price: Very Expensive

• Italian • Gold Coast / Streeterville

Booked 48 times today

Adalina is a refined hospitality destination serving a modern and engaging Italian menu in a timeless yet alluring setting in the heart of Chicago’s Gold Coast neighborhood. Led by Michelin-starred and Top Chef alumni Soo Ahn. Adalina’s menu creates a balance between Northern and Southern cuisine, providing expertly staged shared plates along with strong statement items that satisfy a table. Guests can expect house made extruded and stuffed pastas. Adalina’s offerings will be accompanied with tableside services, and a well curated beverage and wine program that aims to evoke a sense of excitement for guests. Adalina makes the perfect venue for a romantic evening, business dinner or special occasion.For parties larger than 10 guests, please email events@adalinachicago.com to inquire about our Private Dining options and availability.

7. La Serre

4.6

Exceptional(412)

Price: Expensive

• French • West Loop

Booked 78 times today

Inspired by the coastal regions of Provence and Saint-Tropez, La Serre, located in Fulton Market, invites guests into a lush and colorful greenhouse setting. The culinary approach highlights the light and vibrant cuisine of Provence, with a focus on native techniques and ingredients, offering lighter takes on the dishes of the French-Mediterranean landscape. Fresh vegetables, seafood, and all-natural Black Angus beef are expertly prepared on the kitchen’s hardwood charcoal hearth, infusing each dish with incredible wood and charcoal flavors, elevating the ingredients without heavy sauces or seasonings.Whether you're enjoying steak, seafood, or Mediterranean-inspired dishes, La Serre is the perfect destination for romantic dinners, dates, birthdays, or fine dining. The bar offers expertly crafted cocktails and drinks, providing the ideal atmosphere for any occasion, from a casual night out to an elegant celebration.

A photo of Hugo's Frog Bar & Fish House - Chicago restaurant

8. Hugo's Frog Bar & Fish House - Chicago

4.7

Exceptional(5365)

Price: Expensive

• Seafood • Gold Coast / Streeterville

Booked 41 times today

Hugo's Frog Bar & Fish House opened its doors in February 1997 in the heart of Chicago's Gold Coast neighborhood, next to sister restaurant Gibsons Bar & Steakhouse. Over Enjoy the city's finest seafood restaurant, Hugo's continues to be the destination for premier east and west coast oysters, crudos, frog legs, lobster and seasonal fish and shellfish, in addition to Gibsons Prime Angus and Gibsons Grassfed Australian steaks. An extensive wine list, classic cocktail list and selection of impressive signature desserts accompany the menu of fresh seafood, steaks and chops. Beautiful private dining and events spaces available. Gluten-free and vegan options available. Happy Hour Sun-Thurs, 3-6pm.

9. Fioretta

4.6

Exceptional(801)

Price: Very Expensive

• Steak • West Loop

Booked 64 times today

Fioretta is reminiscent of a new-age Copacabana, celebrating old-world Italian cuisine with an opulent twist, a steady flow of impressive cocktails and wine, world-class live entertainment, and a glamorous vibe cast over the entire experience.Seamlessly blending steakhouse fare with elevated versions of old-world Italian cuisine with help from Italian-American Chef, Joe Rizza. The menu pays homage to the Italian immigrants who graciously first introduced Americans to southern Italian classics. Fioretta’s custom-built solid-fuel hearth and open kitchen allows Rizza and his culinary team to impart superb flavor, char and texture to each dish. The menu strives to strike the perfect balance between nostalgia and innovation.

10. River Roast

4.5

Awesome(3286)

Price: Expensive

• American • River North (Chicago)

Booked 43 times today

Situated on the iconic Chicago River with stunning views of downtown, River Roast is a lively social house and gathering place. The menu features contemporary American tavern fare with dramatic presentations of whole roasted chicken, whole roasted fish and slow roasted beef; all carved table-side. The food is handcrafted, yet rustic, with many plates designed for sharing. The bar offers a large selection of local beer, craft cocktails, beer, and wine. With one of the best patios in Chicago, River Roast is a great place to enjoy dining outside on a hot summer afternoon or a crisp fall evening. River Roast Private Events offers six spaces, all with spectacular views, for parties from 10 to 1,000. Saturday and Sunday features our Brunch menu from 11:00AM-3PM. We are open Mon-Fri for lunch and daily for dinner.

See what locals rave about

From verified diners like you

E
Edwardvip
Chicago / Illinois •13 reviews
5.0
Dined 1 day ago
Amir, our waiter, was terrific. He was attentive, pleasant and paid special attention to our grandchildren.
More info
The Palm CourtPrice: Very Expensive• Afternoon Tea• Gold Coast / Streeterville
•
4.7
B
Brian
Chicago / Illinois •1 review
5.0
Dined 1 day ago
Madison was out server and she was fantastic, patient and knew her craft. The food outstanding, the services top notch, definitely a good place for dinner!
More info
Gibsons Bar & Steakhouse - ChicagoPrice: Expensive• Steakhouse• Gold Coast / Streeterville
•
4.7
M
Matt
San Diego •1 review
5.0
Dined 1 day ago
We got the last 2 seats at the bar - last minute - and had a wonderful time. Full jazz ensemble, right volume, delicious food and the bar tender was awesome. We will be back!
More info
Andy's Jazz ClubPrice: Moderate• Contemporary American• River North (Chicago)
•
4.7
A
Andreas
Greece •1 review
5.0
Dined 6 days ago
Food was excellent! Service was very swift. Unluckily the waiter spilled some sauce over one of our coats, and the waiter was trying to ignore it - however the manager reacted very professional (voiding our bottle of wine from the bill). Therefore over all: great, we definitely recommend this place!
More info
KayaoPrice: Expensive• Peruvian• Old Town
•
4.6
L
lashaunda
Chicago / Illinois •1 review
5.0
Dined 7 days ago
I always have such a great experience when dining at maestro’s. The food is impeccable , it’s always so good. The customer service is beyond amazing . We had 3 waiters bringing and serving our sides , we didn’t have to fix our plates at all. The ambiance and aesthetics is just as great. The singer sang us soft beautiful music, while we ate and enjoyed our meal in a dimly lilt environment. My husband and I always enjoy ourselves immensely….. Keep doing a great job and I will continue coming back… if you haven’t been there please go , you will enjoy it all
More info
Mastro's Steakhouse - ChicagoPrice: Expensive• Steakhouse• River North (Chicago)
•
4.7

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Old Town

Best Live Music Restaurants in Old Town

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79 restaurants available nearby

1. Kayao

2. Andy's Jazz Club

3. The Palm Court

4. Mastro's Steakhouse - Chicago

5. Gibsons Bar & Steakhouse - Chicago

6. Adalina

7. La Serre

8. Hugo's Frog Bar & Fish House - Chicago

9. Fioretta

10. River Roast

See what locals rave about

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