7 SPECTACULAR | Mid-Summer Events for All Ages in West Suburban Chicago
- Glancer Magazine
- Jul 1
- 3 min read
Don’t Miss Out On these Super Fun Events Promising Mid-Summer Fun
Summer is here, and it’s time to make the most of the season with unforgettable local experiences! From lively concerts under the stars to vibrant art fairs and family-friendly festivals, there’s something for everyone to enjoy. Whether you’re a music lover, nature enthusiast, or foodie, this list of 7 Spectacular Mid-Summer Fun for All Ages activities will inspire you to soak up the sunshine and create lasting memories. Here’s your ultimate guide to summer fun in your community....
1. Last Fling
CELEBRATING 60 YEARS!
NAPERVILLE–The Naperville Jaycees Last Fling is a FREE to attend family-friendly festival taking place August 29 through September 1, 2025 and is a fun way to say farewell to summer. Visit the Business Expo, Beer Garden, Food Vendors, Jackson Avenue Stage and Family Fun Zone! The Carnival area is open all weekend long; with exclusive access Special Needs Day on Sunday morning. The 2025 Labor Day Parade kicks off Monday at 10amfollowed by a Veterans’ Appreciation Lunch in the Sponsors’ Tent.
2. Naper Nights Summer Concert Series
NAPERVILLE–Naper Nights returns this summer with themed tribute concerts celebrating iconic musical milestones from the 1960s to today. Enjoy live music, great food, drinks, and dancing under the stars at Naper Settlement. A special highlight this year is WAR, performing July 19 to celebrate 50 years of their legendary 1975 album Why Can’t We Be Friends. Don’t miss the original street band's classic hits like “Low Rider,” “Spill the Wine,” and “The Cisco Kid.” Mark your calendar for unforgettable evenings with remaining dates July 18–19, and August 15–16. Rock out with friends and relive music history!
3. Naperville Ale Fest
JULY 12 • 12-5pm
NAPERVILLE–The 2025 Naperville Ale Fest – Summer Edition will take place on Saturday, July 12 from 12pm to 5pm, and will feature over 100 unique craft beers and some of the area’s favorite food trucks. Situated on the grounds of the Naper Settlement, with downtown Naperville as a backdrop, it's the ideal setting to experience craft beer. www.napervillealefest.com
4. CabCab [Cabernet Cabaret] + Wine Fest!
SATURDAY, JULY 19 • 6-11pm
OSWEGO–Grab your family, friends, and your favorite picnic setup—tables, chairs, blankets—and spread out on the polo field for an unforgettable night under the stars. Kids 13 and under are FREE because we believe everyone should be able to join in the fun. This year, summer concert meets wine festival with a ‘90s MIX TAPE twist. Expect all the throwback vibes with a live dream band playing the songs you forgot you loved.
Sip your way through a curated tasting of standout wines, with bottles available to enjoy or take home.
5. Montgomery Fest
MONTGOMERY–Montgomery Fest, held August 15–17, brings the community together for a weekend of classic summer fun. Enjoy live entertainment, a carnival, food vendors, a beer tent, and Family Fest activities. Highlights include a lively parade, a car show, and a carp fishing derby. The weekend wraps up with a dazzling fireworks display over the river. It’s the perfect way for neighbors, friends, and families to celebrate the season in true hometown style.
6. Summer Concert Series
ST. CHARLES–Get ready for some of the best summer fun with free concerts in Lincoln Park, downtown St. Charles! Bring your friends and family every Thursday at 7 p.m. to the gazebo on West Main Street between 4th and 5th Streets. Come early to grab tasty snacks from local restaurants, and don’t forget your blankets and chairs. June 5: Generation; June 12: Valius; June 19: Hillbilly Rockstarz; June 26: Vintage Swing Band; July 3: No Concer; July 10: Johnny Russler & The Beach Bum Band; July 17: The Chicago Experience; July 24: Totally Taylor; July 31: The Messengers; August 7: 7th Heaven. www.stcparks.org/summer-concerts/
7. Block Party-Taste of Batavia
BATAVIA–Celebrate Labor Day weekend at the Downtown Batavia Block Party & Taste of Batavia down at Peg Bond Center! The party comes complete with awesome live music, a Car Show, Pie Bake-off, and free kids area! Tickets are purchased onsite the day of the event. Kids are free and $5 admission for everyone 21 and older. Thank you to our presenting sponsors First State Bank, Prairie Gymnastics Club, and the Congregational Church of Batavia.
