10 Coolest Illinois Towns For A Summer Vacation In 2025

Chicago is by far the most popular city in Illinois, celebrated for its towering skyscrapers, high-end shopping destinations, exquisite dining opportunities, and hip cultural scene. However, its crowded streets and fast-paced life may not set the right precedent for a relaxed summer vacation. Instead of jostling for space with rowdy crowds in downtown Chicago, Illinois offers plenty of small-town charms where you can take it easy in a laid-back environment.

Luckily, these are spread across the state, from the peaceful shores of Lake Michigan to the picturesque banks of the Fox River. From dipping in the toasty lake waters of Highland Park to hiking through rugged jungle trails in Oglesby, the following are the coolest Illinois towns for a summer vacation in 2025.

Princeton

This delightful municipality in Bureau County has an impressive mix of attractions that you can experience throughout the year. However, the warm summer temperature cultivates outdoor adventures, allowing vacationers to discover Princeton's two historic covered bridges. The Captain Swift Covered Bridge is an iconic town landmark, preserving old-world bridge engineering. It stretches over 115 feet long across the Big Bureau Creek and provides an ideal background for a photo. Meanwhile, the Princeton Park District offers at least 200 acres of natural spaces across the town, designed for walkers, picnickers, sports lovers, and more.

Downtown Princeton stages several exciting events, and summers are highlighted by the Shrimp Festival and Brew Hullabaloo in June 2025. This annual spectacle provides an opportunity to sample tasty local beers and wines alongside mouth-watering grilled shrimp. It also features a variety of family-friendly fun.

Highland Park

Highland Park is a gem in Lake County and provides the ideal escape from nearby Chicago. It has an easygoing atmosphere and lies on the serene shores of Lake Michigan, the perfect combo for a summer getaway. Guests head to the sandy shores of Rosewood Beach for a lazy stroll on the sand or a refreshing dip in the blue lake waters. Additionally, Heller Nature Center favors those who appreciate some greenery in their space. This 97-acre sanctuary features a lush forest, prairie, and savanna ecosystem, providing a habitat for native wildlife.

Musical lovers and concerts descend upon Highland Park for the Ravinia Festival. This exciting lineup of stage performances lasts through the summer, from June to September, and features some of the best musical talent in the region.

Geneva

This beautiful Chicago suburb lies on the banks of the Fox River, boasting unprecedented vistas of the iconic waterway. It welcomes summer vacationers to relax in the many outdoor spaces across the town, such as Fabyan Forest Preserve. Serene and secluded, the park charms with its photogenic windmill and setting overlooking the Fox River. It is traversed by the Fox River Trail, which cultivates nonchalant hikes to stretch your legs and admire the flowing river. Access to the river waters fuels a thriving craft brewery scene, and visitors can partake in this local custom by visiting Penrose Brewing Company.

The establishment produces delicious Belgian-style beers, serving them in a pleasant seating area. Meanwhile, the Strawberry Festival is a major summer attraction in Geneva. Starting from the 6th ofJune 2025, it celebrates all things strawberry and treats attendees to luscious cakes, ice creams, slushies, and donuts.

Belleville

Belleville is a vibrant town on the outskirts of St. Louis, Missouri, with a rich manufacturing heritage. Nicknamed "Stove Capital of the World," it presents its backstory at the Labor and Industrial Museum through an extensive collection of over 1,000 artifacts accumulated over time. Tourists can catch the latest summer releases from the Box Office at Lincoln Theatre. The landmark venue showcases first-run Hollywood movies in a family-friendly setting and hosts entertaining stage performances.

If you are a sucker for festivals, make a point of gracing Ainad Shriners Festival of Food in downtown Belleville. This fun extravaganza is planned for June 8, 2025, and promises activities like live music, a cornhole tournament, and great food.

Oglesby

Oglesby is home to a rich network of parks and wilderness areas that are perfect for exploring in the summer weather. If you don't mind breaking a sweat, you can wear comfortable walking shoes for a rugged hike along the isolated trails in Matthiessen State Park. This is the perfect spot to commune with nature in its rawest form, featuring stunning waterfalls and glowing green moss. The reserve is just south of Starved Rock State Park, providing further room for outdoor immersion.

Activities range from bird watching and hiking to fishing and kayaking down the winding waters of the Illinois River. Oglesby hosts multiple summer events that entice tourists with fun in the backcountry. These include the Oglesby Summer Fun Fest and the Oglesby Summer Days Car Craze, scheduled for June and August 2025, respectively.

Galena

In the United States, Galena earns a high spot among the coolest Illinois towns for a summer vacation in 2025, thanks to its busy calendar of summer festivals. Guests are drawn from across the state with its promise of nonstop events, starting with the Great Galena Balloon Race on June 20, 2025. This mesmerizing spectacle decorates the Galena sky with colorful hot air balloons. Summer also sees the Market House Square Arts Festival come to town, allowing regional artists to showcase their creations as attendees jam to live music and enjoy delicious eats.

If you are not attending the festivals, you can take the Galena Trolley Tour to admire the picturesque cityscape of downtown Galena. This open tram ride winds through the town square, exposing travelers to notable landmarks, such as the architecturally pleasing Ulysses S. Grant Home.

Makanda

Makanda entices summer vacationers with a low-key experience in the isolated countryside of southern Illinois. This modest village is a gateway to Giant City State Park, which spans approximately 4,000 acres within the expansive Shawnee National Forest. The reserve is a dream come true for ardent adventurers and provides numerous opportunities for hikers, hunters, and bird watchers. But if you want to up the ante, you can launch skywards for a heart-stopping aerial adventure courtesy of Shawnee Bluff Canopy Tour.

This zipline tour stretches 1,100 feet above the dense canopy of the Shawnee National Forest. Makanda is also known for its wine production, and oenophiles interested in sampling local offerings can visit Blue Sky Vineyard.

Grayslake

This waterfront community, situated about 14 miles from Lake Michigan, is an excellent small-town option for a summer getaway. It is home to Grayslake, a 78-acre recreational reservoir where newcomers indulge in entertaining aquatic activities like paddling, boating, and swimming. Several nature areas allow guests to isolate themselves and enjoy their own company. Prominent among these is the Rollins Savanna Forest Preserve, which provides at least 1,200 uninterrupted acres of massive oaks, prairies, and open fields.

Also, Central Park offers a family-friendly option with picnic areas, walking trails, and a kids' playground. Finally, the annual Grayslake Arts Festival and Wine Tasting is planned for June 7, 2025, and invites art enthusiasts and wine lovers to join the locals in marking a popular spectacle in an upbeat atmosphere.

Danville

Rich history meets thriving arts in this charismatic community of Vermilion County. Danville hosts multiple museums that promise historians an interesting journey into the past. The Vermilion County War Museum displays at least 5,000 war artifacts about different American conflicts, including the Revolutionary War, Civil War, Cold War, and World Wars. Meanwhile, the Vermilion County Museum focuses on the history of the region. It is housed inside a beautiful Italianate building constructed in the mid-19th century.

Art lovers in Danville find a common course at the Fisher Theatre. The 1884 venue hosts thought-provoking live performances that remind the audience of its glory days. Danville's art scene comes to a head during Arts in the Park, which will play out on June 21 & 22, 2025, at Lincoln Park.

Crystal Lake

Crystal Lake encourages tourists to make the most of the hot summer conditions by indulging in its amazing water-based adventures. The lovely community is home to the famous Three Oaks Recreation Area, which provides access to the calm waters of a 330-acre lake, accommodating fishermen, paddleboarders, sailors, kayakers, and canoeists. Vacationers with kids are in for an unforgettable experience at the Urban Air Trampoline and Adventure Park. The facility offers all-around fun featuring open jumping, dodgeball, fitness classes, and parties.

Crystal Lake has a lively arts culture and provides worthwhile viewing opportunities inside the Raue Center for the Arts. The rustic venue dates back to the 1920s and stages a lineup of theatrical productions to entertain all ages, including kids' shows, dramas, concerts, and more.

Although Illinois is special any time of the year, the warm summer temperatures provide the perfect conditions to indulge in all its attractions. Whether you are an outdoor thrill seeker, festival goer, culinary enthusiast, or wine lover, there is no limit to the fun that awaits in the Land of Lincoln. Tourists can select from a long list of options to have fun in these coolest Illinois towns for a summer vacation in 2025, from swimming in Highland Park to hiking in Makanda.