Waukegan

Day Trips

Make the most of your day with our curated plans, packed with Waukegan's hidden gems and unique experiences!

day 1
Exploring Downtown Waukegan
morning
:

Start your day with a delightful breakfast at a local café, where you can enjoy pancakes or an omelet. After breakfast, take a stroll around the historic downtown area, admiring the beautiful architecture and unique shops. Make sure to visit the Waukegan History Museum to learn about the city's rich heritage.

afternoon
:

After lunch at one of the trendy bistros, head to the Genesee Theatre and take a guided tour of this stunning venue, which dates back to the 1920s. Spend the rest of your afternoon relaxing in the nearby Jack Benny Center for the Arts, where you can appreciate local artworks and perhaps catch a workshop. Before evening falls, take a leisurely walk along the Waukegan Harbor to soak in the views of Lake Michigan.

evening
:

Enjoy dinner at a waterfront restaurant, where you can savor freshly caught fish while watching the sunset over the lake. After dinner, check out what's playing at the Genesee Theatre, as it often hosts concerts and performances that cater to a variety of tastes. Conclude your day with a peaceful visit to a nearby park, taking in the evening serenity.

day 2
Beach Day at North Beach
morning
:

Start your sunny day at North Beach with a brisk jog along the shore, or simply relax and enjoy the fresh morning breeze. Grab a quick breakfast from a beachside café, featuring smoothies and pastries. You can also rent a paddleboard or kayak for some early morning water fun.

afternoon
:

After soaking up the sun, enjoy a picnic lunch on the beach, where you can savor sandwiches and snacks while watching the waves. Spend the afternoon swimming, sunbathing, or participating in beach volleyball games with locals and tourists alike. Make sure to visit the nearby Lighthouse Park for a change of scenery and some wonderful photo opportunities.

evening
:

As the sun starts to set, head to a beachside bar for happy hour, enjoying a refreshing drink while listening to live music. Savor dinner from a local food truck, which often features delicious seasonal options that reflect the local food scene. Wrap up your day with a casual stroll along the beach, taking in the peaceful ambiance and night sky.

day 3
Art and Culture
morning
:

Begin your morning with a hearty breakfast at a local diner, known for its classic American dishes. After that, grab your art supplies and join a painting class at a community art studio, where local artists offer workshops. Immerse yourself in creativity as you explore different techniques and express yourself.

afternoon
:

Post-lunch, visit the Waukegan Art District, where you can explore galleries displaying local artwork and installations. Make sure to stop by the Monthly Art Walk if you're there on the first Friday, showcasing different artists and performers. Spend some time at the library, catching up on reading or attending a community lecture.

evening
:

Enjoy dinner at a restaurant renowned for its farm-to-table cuisine, where you can taste the freshest local ingredients. Attend a theater performance or open mic night at a local venue, immersing yourself in the community's vibrant arts scene. Conclude your evening with a nightcap at a cozy bar, reflecting on the day's artistic adventures.

day 4
Nature Discovery
morning
:

Start your day with breakfast at a farm-to-table restaurant, featuring eggs and fresh produce from local farms. Afterward, head to the Waukegan National Beach for a peaceful hike along the nature trails and wetlands. Take your time to observe birds and other wildlife that inhabit the area.

afternoon
:

Pack a lunch to enjoy at the beach or picnic area, with views of the lake to enhance your dining experience. Spend your afternoon biking along the various trails that intertwine through the landscape. Stop to take photos or just enjoy nature's tranquility at scenic overlooks.

evening
:

As evening approaches, consider joining a guided sunset kayaking tour on Lake Michigan, where you can paddle through the calm waters while watching the sun dip below the horizon. For dinner, relax at a casual eatery that offers seafood options. End your night with a stargazing session by the beach, taking in the beauty of the night sky.

day 5
Family Fun Day
morning
:

Kick off your day with breakfast at a family-friendly café, ensuring everyone enjoys their favorite morning meals. After breakfast, head to the Field Museum of Lake County for an exciting exploration of local history and science. Engage in interactive exhibits that keep both kids and adults entertained.

afternoon
:

For lunch, visit a nearby pizzeria that offers a variety of toppings to satisfy everyone's cravings. Afterward, enjoy a fun-filled afternoon at a local park featuring playgrounds, sports fields, and picnic areas. Participate in activities like soccer or kickball with the kids for some quality family bonding.

evening
:

As the day winds down, make dinner at a family-oriented restaurant with kid-friendly menu options, ensuring everyone has something they love. Attend a movie showing at a local theater, giving the family a chance to unwind and enjoy some entertainment together. After the film, grab some ice cream at a local shop for a sweet treat to end the evening.

day 6
Historic Sites Exploration
morning
:

Begin your day with breakfast at a quaint café that highlights the charm of Waukegan. Explore the historic sites in the area, including the former home of comedian Jack Benny, which offers guided tours dotted with entertaining anecdotes. Capture photos of notable landmarks along the way.

afternoon
:

Have lunch at a historic inn that features traditional fare served in a timeless setting. In the afternoon, visit the U.S. Coast Guard Training Center for a chance to learn about this branch of the military and their role in local history. Engage with informative displays and exhibitions.

evening
:

As evening sets in, dine at a historic restaurant known for its charm and delicious cuisine. After dinner, participate in a historical ghost tour, where you can learn about local legends while exploring the city after dark. Finish the night with a drink at a bar that boasts vintage decor and a rich history.

day 7
Sports and Recreation
morning
:

Start with a hearty breakfast at a local café before heading to a nearby sports complex for a morning of fun. Engage in activities like bowling, mini-golf, or perhaps a round of pick-up basketball with friends. This will get your blood pumping and get you energized for the day ahead.

afternoon
:

For lunch, enjoy a meal at a sports bar where you can watch live games on the screens while indulging in hearty fare. Spend the afternoon at a local bowling alley or maximizing your fun at an escape room, testing your skills and teamwork. This active day is sure to be a thrill for sports enthusiasts.

evening
:

Wrap up the day with dinner at a grill specializing in classic American barbecued dishes. Attend a local sporting event, whether it's a minor league baseball game or a local football match, cheering for the home team alongside fellow fans. End the night at a nearby café, sharing highlights of the day's excitement.

day 8
Shopping and Dining Experience
morning
:

Begin your morning with breakfast at a trendy café known for artisanal coffee and homemade pastries. After that, head to the local shopping district, where you can explore a variety of boutiques that showcase unique artisan products. Take your time to browse stores and explore local fashion and crafts.

afternoon
:

Enjoy a leisurely lunch at one of the many restaurants that showcase international cuisine, allowing your taste buds to travel the world. After lunch, visit nearby antique shops and thrift stores for hidden treasures and vintage finds. This afternoon is perfect for discovering unique items while shopping locally.

evening
:

Savor dinner at a rooftop restaurant, where you can relish fine dining accompanied by breathtaking views of the city. Afterward, attend a food festival or farmers' market in the area, bustling with food trucks and vendors providing samples of their best dishes. Wind down at a cozy wine bar, reflecting on the culinary adventures of the day.

day 9
Festivals and Events
morning
:

Kick off your festival day with breakfast at a local establishment that highlights seasonal ingredients. Depending on the day, head to a local festival or event that showcases the city’s vibrant culture through music, art, and food. Immerse yourself in the exciting atmosphere that these community celebrations bring.

afternoon
:

For lunch, indulge in festival food from various vendors, trying out new dishes while exploring the event. Participate in workshops or hands-on activities offered at the festival to engage with locals and learn something new. Continue to enjoy live performances or art displays throughout the afternoon.

evening
:

As the sun sets, enjoy the ambiance of the festival, with twinkling lights creating a magical atmosphere. Savor your dinner from a local food truck, partaking in the local culinary scene. End the night dancing to live music or enjoying other performances, wrapping up an exhilarating day.

Discover Waukegan

Read more in our Waukegan 2025 Travel Guide.

Waukegan Travel Guide