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Orsos Old Town Chicago: Where dirty martinis meet old-world romance

  • Writer: Shannon Heaton
    Shannon Heaton
  • Oct 20, 2024
  • 2 min read

Forget the hustle and bustle of trendy cocktail bars. In the heart of Chicago's charming Old Town lies Orso's, a hidden gem that transports you to a time of elegance and sophistication. This isn't just any bar; it's an old-school Italian haven dripping with ornate decor for the perfect date night.

pianist at grand piano in restaurant

Imagine this... dimmed lighting casts a warm glow over plush booths and a busy bar, filled with locals and visitors alike. As you settle in, the tunes of a talented pianist fill the air, creating a romantic and intimate atmosphere. Add to that the stunning decor – think rich fabrics, exposed brick, and golden finishings for an air of old-world charm.


If you've been in Chicago a while, you might have heard of Orso's for their incredible pasta and Italian fare, but Orso's isn't just about the food. Apart from their incredible pasta (gnocchi and lasagne are crowd favourites and will NOT disappoint), in my eyes, Orso's is also famous for their incredible cocktails, where you can experience the best dirty martini in Chicago... big call - I know!

dirty martini on bar

So, what makes Orsos' dirty martini so special?

  • Authentic Italian charm: Sitting at the bar at Orsos offers a unique escape from the ordinary. It's a place where you can slow down, savor a non-pretentious, perfectly crafted cocktail, and soak in the atmosphere. A martini at the bar is the perfect way to start your evening and settle in for some people watching with regulars and visitors alike.

  • Expert mixology: A skilled artisan, and all round great guy, Jake is our favourite bartender at Orsos,. He knows how to turn a simple drink into a delightful experience - shout out to Jake who takes care of us on each visit!

  • Attention to detail: From the temperature of the martini glass to the ambiance created by the pianist, every detail at Orso's is meticulously considered to enhance your experience.

My tip - Hendrick's, extra dirty with blue cheese olives is the perfect combo.


Whether you're a die-hard martini fan or simply seeking a romantic evening filled with charm, Orso's Old Town is a must-visit. In the summer, the large garden patio and rooftop deck is also a great option!


This hidden gem will leave you with a warm memory and a satisfied palate, from what I think is the best dirty martini in Chicago - tell me I'm wrong...



photographs on wall of fame in restaurant
author drinking martini at bar


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