Best Live Music Restaurants in Old Town

78 restaurants available nearby

1. Andy's Jazz Club

4.7

Exceptional(5111)

Price: Moderate

• Contemporary American • River North (Chicago)

Booked 99 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.

A photo of Mastro's Steakhouse - Chicago restaurant

2. Mastro's Steakhouse - Chicago

4.6

Exceptional(6369)

Price: Expensive

• Steakhouse • River North (Chicago)

Booked 67 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.

3. The Palm Court

4.6

Exceptional(5092)

Price: Very Expensive

• Afternoon Tea • Gold Coast / Streeterville

Booked 73 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 $78 / Kids $35 (3-12)

4. La Serre

4.6

Exceptional(459)

Price: Expensive

• French • West Loop

Booked 124 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.

5. Divan

4.4

Awesome(59)

Price: Very Expensive

• Steakhouse • River North (Chicago)

Booked 25 times today

Located in Chicago’s River North neighborhood, Divan is an Exclusive Steakhouse & Supperclub Experience that features American steakhouse classics with refined European influences, curated by Executive Chef, Mike Sheerin. The 150-seat, multi-level space lends itself to mini-experiences that range from private sommelier-lead wine tastings in the cellar with a range of localized international wines, and premier seating near the live music stage, to late-night champagne service. With impeccable service and a commitment to quality, we invite guests to savor the finest cuts and deepest grooves in an ambiance that seamlessly blends sophistication with warmth, making every dining experience a masterpiece.

6. Geja's Cafe

4.8

Exceptional(5594)

Price: Expensive

• Fondue • Lincoln Park

Booked 64 times today

For over 59 years, fondue dining at Geja’s Café has been a favorite indulgence for Chicagoans as well as out-of-towners. It’s a perfect way to kindle romance, celebrate a special occasion or simply join family and friends for a fun and unforgettable dining experience.To start we offer a Swiss Gruyere cheese fondue, served with fresh breads, fruits and vegetables for dipping. Our crisp house salad, dressed with tangy Dijon vinaigrette, offers a counterpoint to the rich, warm cheese fondue appetizer.Next, you’ll cook your choices of Australian lobster tail, Gulf shrimp, beef tenderloin, fresh sea scallops or boneless chicken breast in a pot of sizzling soybean oil or broth. The main course is served with fresh vegetables and eight gourmet dipping sauces.Our famous chocolate fondue is flamed table-side, and presented with marshmallows for roasting and other delectable dippers.A 4 % operational fee is added to all checks to work in concert with Chicago's One Fair Wage Ordinance.

7. The Evie

4.8

Exceptional(808)

Price: Expensive

• American • River North (Chicago)

Booked 67 times today

Led by a team of lifelong Chicago restaurant figures, The Evie is a locally-owned upscale dining destination located at the heart of the Magnificent Mile. Led by Partner George Archos (Wildberry Café), Chef-Partner Nick Nitti (Forno Rosso, Lucia Rose, Cucina 3 Italian), and Executive Chef Phil Rubino (Spiaggia, L2O, Cicchetti), the restaurant provides city locals and visitors a place to unwind and indulge while overlooking iconic Michigan Avenue. Named after George’s mother and daughter, the concept puts family at the forefront, with an emphasis on warm, Midwestern hospitality. Evie offers full lunch/dinner and weekend brunch, presenting a menu of reimagined American classics and city favorites, spotlighting dishes like chef-crafted sushi rolls, freshly baked breads, Chicago-style Wagyu hotdogs, and USDA prime steaks. Complementing the menu, our dynamic beverage program weaves together seasonality and elegance, featuring an array of classic and craft cocktails, sake, beer & wine.

A photo of Chicago Chop House restaurant

8. Chicago Chop House

4.8

Exceptional(3755)

Price: Very Expensive

• Steakhouse • River North (Chicago)

Booked 36 times today

Experience History & Excellence: Chicago Chop House® legendary menu features exclusively hand-cut in-house USDA prime steaks, fresh mouth watering seafood, decadent house-made sharable sides and irresistible scratch-made desserts to perfectly culminate your dining experience! Immerse yourself in timeless elegance with five-star service and one of a kind ambiance that includes three cozy candle lit floors of seating filled with over 1,400 historic photos of Chicago architecture, sports, entertainment, political figures, and a wall of mayor's. During the beautiful Chicago summers enjoy our outside Courtyard that offers a perfect setting for a moonlit dinner. Chicago Chop House® combines a memorable dining experience with a rich history, making it a beloved original steakhouse in Chicago.

9. Fioretta

4.7

Exceptional(877)

Price: Very Expensive

• Steak • West Loop

Booked 111 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.

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

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

4.7

Exceptional(5421)

Price: Expensive

• Seafood • Gold Coast / Streeterville

Booked 34 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.

See what locals rave about

From verified diners like you

J
Jonny
Chicago / Illinois •2 reviews
5.0
Dined 2 days ago
My girlfriend and I have been trying to do a better job of exploring West Loop restaurants the last couple months. We thoroughly enjoyed all of these restaurants we've recently tried (Komo, Proxi, Hide+Seek, Fora) but La Serre was the best experience out of all of them. The food was phenomenal, service was excellent, and had an energy to it without being 'loud'. Highly recommend
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La SerrePrice: Expensive• French• West Loop
•
4.6
F
Fanchon
Chicago / Illinois •1 review
4.0
Dined 3 days ago
Celebrated my Birthday here. Wish there was something special for the birthday guest. Some of the best lemon drops we ever had. The establishment was beautiful. Ver friendly and accommodating.
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DivanPrice: Very Expensive• Steakhouse• River North (Chicago)
•
4.4
S
ShaLynne
Chicago / Illinois •1 review
5.0
Dined 4 days ago
The food was amazing, the band that played that night did an amazing set! I love the service as well!
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Andy's Jazz ClubPrice: Moderate• Contemporary American• River North (Chicago)
•
4.7
A
Alex
Chicago / Illinois •2 reviews
5.0
Dined 7 days ago
Always a great experience for Holiday Tea at The Drake! We've been coming here for 20+ years. Last couple of times Amir was our server and he's exceptional.. always kind, smiling, and excellent service. Bojan the manager was very kind and accommodating and is a great addition to the Drake team. See you next year!!
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The Palm CourtPrice: Very Expensive• Afternoon Tea• Gold Coast / Streeterville
•
4.6
B
BrandonVIP
Detroit / Eastern Michigan •24 reviews
5.0
Dined on Jan 3, 2025
Everything was excellent I’m so glad I decided to try it again since the one in New York was so good. My girlfriend and I just love the live entertainment during dinner the lady was fantastic. Definitely a 5/5 from me!
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Mastro's Steakhouse - ChicagoPrice: Expensive• Steakhouse• River North (Chicago)
•
4.6

Best Live Music Restaurants in Old Town

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78 restaurants available nearby

1. Andy's Jazz Club

2. Mastro's Steakhouse - Chicago

3. The Palm Court

4. La Serre

5. Divan

6. Geja's Cafe

7. The Evie

8. Chicago Chop House

9. Fioretta

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

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