Events

A little Sinatra, a little mystery, and a whole lot of Halloween spirit!

Step into an evening of timeless elegance with Sam Magdal, Chicagoland's charismatic crooner, bringing the unforgettable sounds of Frank Sinatra and the golden age of swing to DiBenedetto Trattoria!

This Halloween Eve, we're adding a playful twist to our Friday night tradition.

🦇 Costumes are encouraged! Whether you arrive dressed as a glamorous Hollywood star, a mysterious masquerade guest, or your favorite Halloween character, come ready for a memorable night!

🍷 Sip on handcrafted cocktails, enjoy authentic Italian cuisine, and let the smooth sounds of “Ol' Blue Eyes” set the mood.

📅 Friday, October 30, 2026 🕡 6:30 PM – 9:30 PM

🎶 Live Sinatra tribute with Sam Magdal 🎭 Halloween costumes welcome 🍸 Cocktails, fine wines & Italian dining ✨ A festive evening with a touch of vintage glamour

Come for the dinner. Stay for the music. Dress for the occasion!

Reservations highly recommended.

There’s something special about dinner accompanied by the sound of a live piano.

Join us at DiBenedetto Trattoria as pianist Ed Collins returns for an evening of beautiful music, great food, and good company.

Settle in with your favorite Italian dish and a bottle of wine while Ed creates the perfect soundtrack for a relaxing Friday night.

📅 Friday, November 6, 2026 🕡 6:30 PM – 9:30 PM

🍝 Authentic Italian cuisine 🍷 Fine wines & handcrafted cocktails 🎹 Live piano throughout the evening

Bring someone special, gather a few friends, and come make some memories with us.

Reservations recommended.

📍 DiBenedetto Trattoria 1766 W Algonquin Rd, Hoffman Estates, IL ☎️ (847) 496-5016

Some nights are meant to be unforgettable...

Step into the timeless charm of the Rat Pack era as Sam Magdal returns to DiBenedetto Trattoria for an evening inspired by the legendary Frank Sinatra.

With his charismatic stage presence and smooth interpretations of beloved classics, Sam brings the romance, nostalgia, and sophistication of a bygone era to life.

🍷 Picture this: candlelit tables, a beautiful glass of Italian wine, delicious cuisine, and the unforgettable melodies of “Ol' Blue Eyes” filling the room.

Whether you're celebrating a special occasion, enjoying date night, or simply treating yourself to a wonderful evening, this is your invitation to slow down and savor the moment.

📅 Friday, November 13, 2026 🕡 6:30 PM – 9:30 PM

🎶 Live Frank Sinatra tribute 🍝 Authentic Italian dining 🍷 Fine wines & handcrafted cocktails ❤️ A perfect evening for two or a gathering with friends

Because great music, great food, and great company never go out of style.

✨ Reservations recommended.

📍 DiBenedetto Trattoria 1766 W Algonquin Rd, Hoffman Estates, IL ☎️ (847) 496-5016 🌐 dibenedettotrattoria.com

✨ Good vibes, great music, and a Friday night worth celebrating!

Get ready for an entertaining evening as Denise Armour returns to DiBenedetto Trattoria with her signature “A Mix of Music!”

With over 20 years of professional performing experience, Denise knows how to bring a room to life! From soulful Motown classics and smooth R&B favorites to upbeat Disco, Dance hits, and beautiful ballads, there's something for everyone to enjoy.

🎶 Recognize a favorite song? Sing along! Feeling the rhythm? Don't be shy about showing off a few dance moves!

🍷 Gather your friends, enjoy a delicious Italian dinner, share a bottle of wine, and kick off the weekend with music that makes you smile.

📅 Friday, November 20, 2026 🕡 6:30 PM – 9:30 PM

🎵 Motown • R&B • Disco • Dance • Classics 🍝 Authentic Italian cuisine 🍸 Fine wines & handcrafted cocktails ✨ A fun night for couples, friends, and music lovers

Come hungry. Leave happy. Take the music home in your heart!

Reservations recommended.

📍 DiBenedetto Trattoria 1766 W Algonquin Rd, Hoffman Estates, IL ☎️ (847) 496-5016 🌐 dibenedettotrattoria.com

The holiday gathering doesn't have to end on Thanksgiving!

After the cooking, celebrations, and Black Friday shopping, treat yourself and your loved ones to a relaxing evening of Italian cuisine, fine wine, and beautiful live music at DiBenedetto Trattoria.

🎤 John Vatasoiu returns with his signature blend of timeless classics and romantic international favorites, featuring music inspired by Frank Sinatra, Dean Martin, Julio Iglesias, Eros Ramazzotti, and more.

Whether you're entertaining family from out of town, reconnecting with friends, or enjoying a romantic evening for two, let us take care of dinner while John sets the mood.

📅 Friday, November 27, 2026 🕡 6:30 PM – 9:30 PM

🍝 Authentic Italian cuisine 🍷 Fine wines & handcrafted cocktails 🎶 Timeless classics & international favorites ❤️ Good food, great company, beautiful memories

Skip the leftovers. Gather around our table instead!

✨ Reservations recommended.

📍 DiBenedetto Trattoria 1766 W Algonquin Rd, Hoffman Estates, IL ☎️ (847) 496-5016 🌐 dibenedettotrattoria.com