Known for telling "big stories, up close" the Lifeline Theatre, 6912 N Glenwood in Chicago, has both a mainstage and a kid's series, so you're bound to find something you'd like to see. This certificate gets you two tickets, although some restrictions apply.

And when you do settle in on the show you'd like to see, be sure to schedule enough time for a jaunt just a bit further north into Evanston for a delicious meal at Dave's Italian Kitchen. They put their focus on preparing delicious, homemade food, which is why they didn't name the place "Dave's Italian Dining Room," their website points out. The kitchen takes up a large share of the space at their 1635 Chicago location, but you and your date won't have to worry about getting a table -- or paying for your meals, actually. With this certificate in hand, you'll enjoy $50 worth of dinner for two on the house.