Best Live Music Restaurants in Downtown / Loop

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchMexican

Regions

ChicagoNear WestNorthwest Suburbs

Neighborhoods

Albany ParkBelmont Central / CraginBronzevilleBucktown / Wicker ParkChina TownCicero

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Award-winning

MICHELIN

Accessibility

Wheelchair access

78 restaurants available nearby

How are Featured results ranked

A photo of State and Lake Chicago Tavern restaurant

1. State and Lake Chicago Tavern

4.3

Awesome(1588)

$$$$Price: Moderate

• American • Downtown / Loop

Booked 18 times today

Located in the heart of downtown Chicago at the iconic corner of State and Lake Streets, State and Lake Chicago Tavern is a spirited restaurant and bar featuring elevated American tavern fare, alongside fine wine, expertly prepared cocktails, an unrivaled local beer selection and live music every weekend. An inviting gathering spot for residents and visitors alike, step into a special place where hospitality is always on the menu, and everyone knows your name.Envisioned by Chef Steven Chiappetti – an esteemed, decades-long culinary fixture in Chicago – State and Lake’s menu offers contemporary comfort food classics crafted with traditional heart yet modern hand. Whether seeking a juicy burger, a bright and hearty salad or a comforting bowl of French onion soup, there’s something on the menu for every craving, every day. Cozy enough for casual meet-ups and stylish enough for business, our welcoming space showcases distinctive cork floors, rich leather walls and plush banquettes.

2. Boleo

4.5

Awesome(580)

$$$$Price: Moderate

• Latin American • Downtown / Loop

Booked 12 times today

The cuisine and culture of Latin America make their way to the Windy City in our industrial-chic rooftop bar and lounge, Boleo, where you can find small plates for snacking and sharing, delicious cocktails that transport you to Peru, and house music that will make you want to learn to salsa. Come rain or shine we have you covered with our retractable roof!

3. Bar Pendry

4.3

Awesome(40)

$$$$Price: Expensive

• Cocktail Bar • River North (Chicago)

Off the Pendry Chicago lobby within the historic Carbide & Carbon building, Bar Pendry is a celebration of a classic Chicago cocktail bar. Walk-ins are always encouraged, with reservations taken only for Boozy Tea. With interiors designed by world-renowned design firm Studio Munge, the sophisticated lounge is tucked behind heavy floor-to-ceiling drapery and boasts a dark and moody atmosphere with custom leather sofas, vintage rugs, cozy banquettes and a curated art collection. Anchored around a double-sided fireplace, the 54-person bar offers guests with a selection of classic and seasonal cocktails, wine and local beers along with a menu of elevated bar bites by Pendry Chicago’s Executive Mark Shoemaker and Sunday Afternoon Boozy Tea, available by reservation only.

4. Andy's Jazz Club

4.7

Exceptional(5252)

$$$$Price: Moderate

• Contemporary American • River North (Chicago)

Booked 95 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

5. Mastro's Steakhouse - Chicago

4.5

Awesome(6451)

$$$$Price: Expensive

• Steakhouse • River North (Chicago)

Booked 35 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.

6. RL Restaurant

4.8

Exceptional(7500)

$$$$Price: Expensive

• American • Gold Coast / Streeterville

Booked 110 times today

If you do not find availability online, please call the restaurant directly at 312-475-1100.Located adjacent to the Ralph Lauren Chicago flagship store on Michigan Avenue, RL Restaurant features the vision and décor of Ralph Lauren in a modern club atmosphere. RL Restaurant offers classic American cuisine inspired by Ralph Lauren’s personal favorites. Seasonal dishes range from a chopped vegetable salad to a lobster roll sandwich, grilled fish of the day and steaks. On the cocktail list, guests can choose from classic drinks and a diverse selection of wines and other fine spirits.

7. Fioretta

4.7

Exceptional(1023)

$$$$Price: Very Expensive

• Steak • West Loop

Booked 75 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 Untitled Supper Club restaurant

8. Untitled Supper Club

4.6

Exceptional(2947)

$$$$Price: Expensive

• American • River North (Chicago)

Booked 24 times today

Dress Code: Business Casual is expected - No Shorts, Tee Shirts, Athletic Attire, sandals, gym shoes are permitted. Final decisions are based on the sole discretion of management. *Please notate if you have a room or entertainment preference. Requests cannot be guaranteed, but we will do our best to accommodate.*With its vintage, Prohibition Era-inspired design, Untitled has been a darling of Chicago nightlife and fine dining since opening in 2011. The sumptuous 18,000 square-foot restaurant, bar and live entertainment space hosts the largest selection of American whiskies in the world .Their dining menu includes shareable bites, perfect pastas and beautifully creative desserts; with eight Michelin Bib Gourmand awards, their cuisine is sure to satisfy any palette. The best part? While you dine and drink the night away, you can enjoy world-class entertainment with weekly music and titillating cabaret-style performances from Chicago's finest.Untitled is a 21+ establishment.

9. The Evie

4.8

Exceptional(947)

$$$$Price: Expensive

• American • River North (Chicago)

Booked 73 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.

10. Divan

4.0

Excellent(147)

$$$$Price: Moderate

• Steakhouse • River North (Chicago)

Booked 26 times today

Located in Chicago's vibrant River North neighborhood, Divan Chicago is a modern steakhouse and supper club offering an upscale dining experience with American steakhouse classics and refined European influences. Enjoy premium steaks, fresh seafood, and late-night dining in a stylish setting with live music and a private dining room available. Join us for happy hour and experience one of River North's most sophisticated destinations.

See what locals rave about

From verified diners like you

K
KellyVIP
Seattle / Eastern Washington •4 reviews
5.0
Dined 2 days ago
Great experience! Easy to get to, friendly staff, and amazing Jazz musicians.
More info
Andy's Jazz ClubPrice: Moderate• Contemporary American• River North (Chicago)
•
4.7
N
NORM
Chicago / Illinois •15 reviews
5.0
Dined 7 days ago
GREAT LOCATION FOR EATS & DRINKS B4 A SHOW IN THE THEATER DISTRICT. SUPER CLOSE TO CHICAGO THEATER:)
More info
State and Lake Chicago TavernPrice: Moderate• American• Downtown / Loop
•
4.3
C
Christiane
Chicago / Illinois •3 reviews
5.0
Dined on Apr 15, 2025
Excellent service! Beautiful live background music. Wonderful choices of steaks. My highlight was the bacon appetizer! Goodness, yum. Oh, and the butter cake and the cherry crisp. Patrick was a fabulous server with excellent skills, recommendations and sense of humor!
More info
Mastro's Steakhouse - ChicagoPrice: Expensive• Steakhouse• River North (Chicago)
•
4.5
K
Kim
Hawaii •1 review
5.0
Dined on Apr 13, 2025
We had a lovely experience at this restaurant! Hector, the bartender was so great! Gave us advise on the menu, made great drinks! Had table side guac, delicious. Then we had several small plates, empanadas, grilled octopus and the dessert empanadas were great! Nice atmosphere!
More info
BoleoPrice: Moderate• Latin American• Downtown / Loop
•
4.5
OT
OpenTable DinerVIP
Chicago / Illinois •2 reviews
5.0
Dined on Feb 11, 2024
Everything was really good!! Loved the tea time experience!!
More info
Bar PendryPrice: Expensive• Cocktail Bar• River North (Chicago)
•
4.3

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