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Best Live Music Restaurants in Old Town

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78 restaurants available nearby

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A photo of Andy's Jazz Club restaurant
4.7
Exceptional(5274)
Price: Moderate
• Contemporary American • River North (Chicago)
Booked 111 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
4.5
Awesome(6456)
Price: Expensive
• Steakhouse • River North (Chicago)
Booked 78 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 Divan restaurant
4.1
Excellent(161)
Price: Moderate
• Steakhouse • River North (Chicago)
Booked 34 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.
A photo of Fioretta restaurant
4.7
Exceptional(1046)
Price: Very Expensive
• Steak • West Loop
Booked 51 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 The Palm Court restaurant
4.7
Exceptional(5197)
Price: Very Expensive
• Afternoon Tea • Gold Coast / Streeterville
Booked 45 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)Valet available at $26 for 3 hours
A photo of Turquoise restaurant
4.7
Exceptional(1277)
Price: Moderate
• Mediterranean • Roscoe Village
Booked 24 times today
Turquoise Cafe & Restaurant, located in Chicago's Roscoe Village, is a culinary gem blending the best of Turkish and Italian cuisines in a captivating and inviting atmosphere. Owned by a passionate female entrepreneur, this vibrant establishment offers an extensive menu of tantalizing kebabs, handmade pastas, fresh seafood, mezze platters, and wood-fired flatbreads.🍷 With our carefully curated wine selection, you can feel the spirit of the Mediterranean in every sip, making your special moments even more memorable. Red, white, or rosé…🎶 With live music on weekends and a delightful Sunday brunch featuring an authentic Turkish Serpme Breakfast, Turquoise Cafe & Restaurant provides a remarkable culinary journey.
A photo of The Evie restaurant
4.8
Exceptional(970)
Price: Expensive
• American • River North (Chicago)
Booked 83 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 Guinness Open Gate Brewery - Chicago restaurant
4.5
Awesome(183)
Price: Expensive
• Brewery • West Loop
Booked 28 times today
Where 260 years of Irish Brewing expertise meets American beer creativity. Inspired by Chicago, crafted by Guinness. Look out, Chicago.The Guinness Open Gate Brewery Chicago features a Taproom, Restaurant, and the first ever Guinness Bakery, all located right in the heart of Chicago's West Loop. Come indulge both your curiosity and your tastebuds, while experimenting with a new world of flavor.
A photo of Geja's Cafe restaurant
4.9
Exceptional(5683)
Price: Expensive
• Fondue • Lincoln Park
Booked 25 times today
For over 60 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.
A photo of Untitled Supper Club restaurant
4.5
Awesome(2963)
Price: Expensive
• American • River North (Chicago)
Booked 37 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.

See what locals rave about

From verified diners like you
From verified diners like you
  • marciaVIP
    Los Angeles •73 reviews
    5.0
    Dined 1 day ago
    What an amazing time! Excellent service from check in at entry desk to final bill. Great seating (in honor of anniversary?), lovely harpist, excellent waiter who exceeded our expectations. A champagne toast on the house plus chocolaty mini cake w candle. It couldn’t have been nicer. Would highly recommend … !!!
    More info
    The Palm CourtPrice: Very Expensive• Afternoon Tea• Gold Coast / Streeterville
    4.7
  • Bailey
    Los Angeles •1 review
    5.0
    Dined 1 day ago
    More restaurant than sit down “club” but a very good experience and amazing music.
    More info
    Andy's Jazz ClubPrice: Moderate• Contemporary American• River North (Chicago)
    4.7
  • Kathryn
    Kansas City / Kansas •3 reviews
    5.0
    Dined 2 days ago
    We were flying in from out of town and our flight was delayed. We were going to miss our reservation at Divan. They accommodated us perfectly and we had an amazing meal! So yummy. And the wine list...don't get me started...amazing!
    More info
    DivanPrice: Moderate• Steakhouse• River North (Chicago)
    4.1
  • Jay
    San Diego •6 reviews
    5.0
    Dined 2 days ago
    Filet was excellent, seasoned nicely, cooked perfectly, medium rare! My wife had the sea bass, also excellent. She wanted lobster Mac and cheese, it was OK, a little bland, but very cheesy. For dessert, had the butter cake...it was outstanding! Served with vanilla ice cream and whipped cream. It's a large serving, so ensure there are others to share with. Overall a great time, service good.
    More info
    Mastro's Steakhouse - ChicagoPrice: Expensive• Steakhouse• River North (Chicago)
    4.5
  • John
    Chicago / Illinois •7 reviews
    5.0
    Dined 3 days ago
    Is it pricey? Yes. Is it noisy? Yes. Is it worth it? Definitely yes. If you just want a steak and old fashioned, there are more economical options even within a few blocks. Fioretta is about the show. The food is amazing, even the broccoli drew raves. Service was impressive as well. It's one of the few places who will still make Caesar salads tableside. The steaks are pure showmanship. The non-steak options are excellent as well. They were able to accommodate a number of dietary restrictions without any issues and still deliver delicious meals and cocktails to everyone present. Highly recommended for special events or when you want to make a big impression.
    More info
    FiorettaPrice: Very Expensive• Steak• West Loop
    4.7
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