Spend the day at Waukegan Municipal Beach. It’s been renovated and now hosts comedy shows, concerts & local events.
Once upon a time (in the 1920s), this theatre was the place to see movies in town.
Check out our list of things to do in Waukegan – there’s something for every season! 1. But you’ll be happy to know it’s easy to find new and fun things to do living in Waukegan! This large city has many hidden gems and exciting things to do for date night. Waukegan is a short hour and a half drive from downtown Chicago, making the trip doable but just long enough to be a deterrent for a night out in the Windy City. If you’re new to Waukegan, having just moved here, you may think keeping date night fun is tough.