15 Date Night Ideas in Waukegan


If you’re new to Waukegan, having just moved here, you may think keeping date night fun is tough. 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. 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.  Check out our list of things to do in Waukegan – there’s something for every season!

1. See a show at the Genesee Theatre

Once upon a time (in the 1920s), this theatre was the place to see movies in town.  It’s been renovated and now hosts comedy shows, concerts & local events. Spend the day at Waukegan Municipal Beach. 

2. Spend the day at Waukegan Municipal Beach. 

This public beach is the perfect place to relax and perhaps share a picnic or a romantic walk along the shore, but it's a great place to get away from the crowd and get some sun, a refreshing lake breeze, and dip your toes in the water.  There is nothing more beautiful than relaxing in the sand, especially with someone you care about! 

3. Take a hike at  Lyons Woods Forrest Preserve.

The preserve is over 345 acres with about 4 miles of trails throughout; it’s great for birding, walking, and biking, and, of course, hiking! This preserve is beautiful in all four seasons and offers a lovely romantic backdrop for all of them.  Enjoy the spectacular fall foliage, snowshoeing in a winter wonderland, searching out early flowers in spring, or looking for butterflies in summer – there's something perfect about it in each season that helps set the romantic mood. 

Visit the east side where there are binoculars for bird watching and don’t forget your GPS to go Geocaching.  Geocaching is an outdoor recreational activity in which participants use a Global Positioning System receiver or mobile device and other navigational techniques to hide and seek containers, called “geocaches” or “caches”, at specific locations marked by coordinates all over the world. Spend a lovely day together enjoying nature and each other.

Pro tip: Go early without your date and leave a love note in a cache!

4. FORE! Time for some fun mini-golf! 

The People's Choice Family Fun Park is the place to go. You can even play a few rounds of putt-putt in the dark under glow lights!  This fun center offers a full arcade as well, so you can win your sweetie a prize, or engage in some harmless competition.  Check out the Rocky’s Vegas Strip where you can play video casino slot games and maybe win real cash (must be 21 to play). Try your luck! There’s pizza and cold beer available as well.

5. Go to the light at Waukegan Harbor Lighthouse. 

A truly romantic spot, you'll want to hold hands as you walk to the end, not just because it’s a sweet thing to do but to keep from falling in!  Caution: There are no railings on this walk.  Consider doing a stroll at sunset and you will be rewarded with a spectacular view.  You can see the City of Chicago at the end of the pier.

Located at the end of the Government Pier on Lake Michigan, this is an active lighthouse used by the US Coast Guard. What a fabulous place for couple selfies! 

6. Go Shopping! 

Some people think the perfect date would be shopping at the Gurnee Mills Mall.  This place has everything that makes a mall great.  There is a ton to look at, people watching, and plenty of strolling. Check out over 200 shops and grab a quick bite to eat at the food court or a sit-down meal at the Rainforest Café.

7. Find out if you have what it takes at 60 To Escape. 

You can challenge yourself (and your relationship) using problem-solving skills and teamwork to escape. Choose your escape from a variety of situations that each has a different theme and feel. Choose the one you and your date will most likely complete. A few themes to choose from:

  • Blast from the Past: Try to find out what happened to the owner of the arcade – who was supposedly trying to “build a machine” and then disappeared.  Maybe you can save him and all of us!
  • Museum: Become a thief and steal a priceless jewel in the museum. Can you hack the security system and get the priceless diamond before the guards get back? 
  • Bomb Squad: There’s not enough time to evacuate everyone.  You have to locate and diffuse the hidden bomb before it goes boom! 

These are just a few of the options available, any of which will challenge you and your date using brainpower and teamwork to complete the challenge.

8. Check into your inner child and visit Bowen Park.

Plan to spend the day at this large, elaborate park that has something to offer for everyone! There are ball fields and a sports complex on one end and a hiking area with beautiful trails and many diverse types of plants, birds, and wildlife to explore on another end of the park. And, yet, another area contains amazing playgrounds, including picnic areas and a skate park.  This park has it all! You'll also find The Waukegan Historical Society and the Jack Benny Center for the Arts at this park. Head here anytime for relaxation or sport or fun!

9. Take the Plunge (The Waukegan Polar Bear Plunge)

Do something community-minded and take a plunge in freezing Lake Michigan to benefit the Special Recreation Services of Northern Lake County.  There is nothing quite as invigorating as putting on your bathing suit and jumping into an ice-cold lake unless it’s heating up afterward. Taking the plunge will make it a date night that you won’t forget. If you're competitive with each other, see who can raise the most money for your plunge!

10. Check out Ray Bradbury’s Dandelion Wine Fine Arts Festival.

Bowen Park. There’s nothing as fun as an outdoor festival, and this one goes on all day!  Strolling through the park enjoying live music, looking at incredible art, and enjoying each other is a perfect way to spend time together.

11. Waukegan’s Independence Day Parade

Celebrate the red, white and blue at Waukegan’s Independence Day Parade celebrating America’s independence. Who doesn’t love a parade? 

12. Take a trip back into the history of Waukegan! 

Visit the Waukegan History Museum.  Located in one of the oldest homes in Lake County, built in 1843. The former home of past Mayor of Chicago John Haines, it’s now set up as a period Victorian home and incorporates photographs, artifacts and exhibits showcasing the history of Waukegan. Don’t miss the Waukegan Top 50 Exhibit, which showcases what could be the top 50 historical events in the town. Explore the history of Jack Benny, one of Waukegan’s most famous residents! It’s a fabulous way to spend a day with your favorite person, exploring the past! 

13. Take a run! Lace-up for the George Bridges 5K Run/Walk. 

It's not just a run, you’re helping fund the Special Recreation Services of Northern Lake County (SRSNLC), which assists individuals with disabilities to participate in camps, athletics, health and fitness programs, and much more.  

14. Lace-up the old bowling shoes, warm up your arms and go bowling.

Nothing is more fun than a little friendly competition and at  Sunset Bowl it's all about the pins. All 10 of them, and who can knock down the most.  Can you get a perfect 300?  Better yet, join a league and have a date night every week!  Plus, nothing beats bowling, beer, and pizza.

15. Couple Skate! 

If your idea of fun is whizzing around on a board or skates, you need to head to the Waukegan Skate Park and shred!  It's the perfect opportunity to teach your date about something you love if they’re a novice. With three separate sections for beginner, intermediate, and expert skaters, hone your skater skills and skate off into the sunset together!

That’s just the beginning of the fantastic dates to be had in Waukegan.  This list doesn’t include any of the fabulous restaurants, breweries, coffee shops, and eateries that could be great dinner dates.  So after you’ve finished using your storage unit in Waukegan, go out and celebrate with someone special! It's easy to find some unique and fun date night ideas for special times with your special someone in this busy town. 

About the author

Wendy Del Monte

Wendy Del Monte is a Transplanted Texan living in New England who loves to explore new places and discover their history. She enjoys the outdoors, animals, and old-fashioned country fairs.

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