Go big. Eat well. Laugh until it hurts.

This is the kind of Chicago night you plan around. Start with $1,000 to spend at Chicago Cut Steakhouse, one of the city’s premier destinations for an unforgettable steakhouse experience. Bring your favorite people, order exactly what you want, and settle in for a dinner worth dressing up for.

Then keep the night going with two tickets to a weeknight comedy show at The Second City, where some of the biggest names in comedy got their start. It’s the perfect way to cap off an already incredible evening—with great food, great drinks, and a whole lot of laughs.