Penumbra (Chicago)
Dollar for dollar, I don’t think there’s a better steakhouse in Chicago.
Where else can you get a high-quality steak dinner for under 30 bucks? Your choice of a New York Strip, Rib Eye, or Flat Iron dinner for $29. That includes a side, a salad, and a complimentary soup ‘appetizer.’

Flat Iron steak. Chimichurri sauce. Roasted poblano on the side shaped like a frickin’ heart. What more could you want on a date?
But what really makes Penumbra stand out is the restaurant’s design. Our table was in its own comfy little area with a privacy curtain. I couldn’t hear our neighbor’s conversations and they couldn’t hear mine. They couldn’t see us. I couldn’t see them. It was awesome. Like our own little fort well-provisioned with wine and red meat. Dim lighting, romantic vibe, and excellent service.
Sure, you could go to Morton’s or Gibsons and spend a small fortune on a steak and some a la carte sides…but why would you when you can go to Penumbra and pay a fraction of the price for a stellar steak meal?

Molten Brandy Truffle Cake. I had to take this pic fast so I could eat this delicious sucker while it was still hot and gooey.