Club Lucky

Belle Kendrick
Sep 9
1 min read

If you're searching for an Italian restaurant in Chicago with a retro vibe and a killer martini menu, Club Lucky is your next stop. After hearing several recommendations, I finally made a Friday night reservation to experience what this neighborhood favorite had to offer.

We kicked things off with one of Club Lucky’s famous martinis. I opted for the Tequila Martini with a lemon twist, which was strong and very chilled.

Close-up of a tequila martini with lemon twist on a white tablecloth.

To start the meal, we shared two appetizers:

The Famous Grilled Calamari, which had a bit too much char for my taste.
The Fried Ravioli, a nightly special, was a highlight—crispy, cheesy, and packed with flavor.

Grilled calamari with char marks, served with lemon wedges.

Fried ravioli appetizer served on a white plate with marinara dipping sauce.

For our entrees, we split two pasta dishes:

The Penne Arrabbiata, served with a spicy tomato base and fresh basil, had a solid heat kick.
The Homemade Tortellini in vodka sauce was the standout of the night—creamy, comforting, and rich without being too heavy.

Penne arrabbiata pasta in a red spicy tomato sauce garnished with basil

Homemade tortellini in vodka sauce, topped with Parmesan cheese

We couldn’t resist the Warm Toll House Cookie served with vanilla ice cream. While it leaned more cake-like than cookie, it still hit the spot for a sweet ending to our savory meal.

Warm Toll House cookie cake served with a scoop of vanilla ice cream

Club Lucky offers a nostalgic dining experience with its 1950s-style décor, cozy booths, and dim lighting—perfect for a weekend dinner or a fun night out. Whether you're visiting for their martinis or hearty Italian fare, it's easy to see why Club Lucky is a Bucktown staple.