1 Crosby’s Kitchen (3455 N Southport Ave, 773-883-2525)
Kids 12 and under eat free every day from 4–6pm at this new Southport Corridor favorite. But that’s not the best part. Valet park your stroller, get the kids settled with crayons, Shirley Temples and chicken tenders, then kick back with your own cocktail and one of the restaurant’s stellar rotisserie entrées (chicken, prime rib, leg of lamb). At meal’s end, come together to share a decadent cookie skillet, topped with vanilla ice cream.
2 Leona's Restaurant (6935 N Sheridan Rd, 773-764-5757)
Kids up to 8 years old can enjoy a free meal, including pizza, pasta, chicken, and mac and cheese, then work off some energy in the enormous playroom outfitted with TVs playing popular kids movies.
3 Rockit Burger Bar(3700 N Clark St, 773-645-4400)
You’ll have just a little less guilt about chowing down on the big, juicy Black Angus burgers at this Wrigleyville spot when your kids 12 and under eat free Thursday-Sunday from 5–7pm. They can pick from a traditional burger, turkey burger, grilled cheese and other options. There are veg, chicken and turkey alternatives for grown-ups, too.
4 Pinstripes(1150 Willow Rd, Northbrook, 847-480-2323)
There’s something for everyone at this enormous restaurant/entertainment complex (part of a chain with locations in Schaumburg and South Barrington) that serves Italian-American cuisine and houses bowling, bocce and an outdoor patio with fire pit. Kids eat free on Sundays after 5pm from a menu of standards including chicken strips and pizza.
5 Butch McGuire’s(20 W Division St, 312-787-4318)
Saturday and Sunday breakfast/brunch is on the house for kids with paying adults (limit two kids per table) at this Division Street staple. Grown-ups can choose from entrées including eggs Benedict, corned beef hash and “car bomb” French toast, dipped in a batter of Guinness and Baileys and served with Jameson maple syrup. For kids, choices include pancakes and breakfast pizza.