With long days and warm nights, summer weekends are made for exploring. Whether you’re staying local or venturing out, here are a few events worth adding to your calendar.
Go Back in Time at Retro on Roscoe
Roscoe Village celebrates summer with three stages of live music, vintage vibes, and endless neighborhood fun. Cover bands keep the crowd dancing to hits from every era, while a classic car show lines the streets with chrome and nostalgia. Families will find a kids’ zone with inflatables and games, and food vendors dish up everything from festival favorites to local bites.
Date: September 5-7
Time: Fri 5PM-10PM; Sat 12PM-10PM; Sun 12PM-8PM
Cost: $15 Suggested Donation
Location: 2000 W. Roscoe St.
More Info: roscoevillage.org
Get a Taste of Chicago
The city’s signature food fest returns with a lineup as sprawling as ever. More than 40 local restaurants and food trucks-from Harold’s Chicken to Connie’s Pizza to Soul & Smoke-serve up Chicago staples and global bites, while stages across Grant Park showcase live music, including Lupe Fiasco, JoJo, and Elvis Crespo. Festivalgoers can also join Chicago SummerDance for lessons in everything from salsa to swing, or belt it out at karaoke for a shot at $500.
Date: September 5-7
Time: 11AM-9PM
Cost: Free
Location: Grant Park, 235 S. Columbus Dr.
More Info: chicago.gov
Give Back at the ALS Compassionate Care Fundraiser
Support a good cause while savoring good food at this benefit for the ALS Compassionate Care Fund. The evening features a ticketed spread of food and drinks, plus live classical guitar to set the mood. Guests can also bid on silent auction items, with proceeds going to CCALS programs that provide care and resources for people living with ALS. It’s an intimate way to give back and enjoy yourself in the process.
Date: September 7
Time: 4PM-7PM
Cost: $35
Location: Taste Food & Wine, 1506 W. Jarvis Ave.
More Info: taste-food-wine.square.site
Stories Come Alive at Printers Row Lit Fest
Book lovers, rejoice: the Printers Row Lit Fest is back for its 40th year. The Midwest’s largest outdoor literary showcase draws more than 100,000 visitors and 150 exhibitors to the historic South Loop. Visitors can browse works from indie presses, established publishers, and rare book dealers, or sit in on author panels and signings. Whether you’re after a first edition, the latest release, or just a full day of literary buzz, this is the place to be.
Date: September 6-7
Time: 10AM-6PM
Cost: Free
Location: S. Dearborn from Ida B Wells Dr. to Polk St.
More Info: printersrowlitfest.org
Feel Nostalgic at Throwback Music Fest
Gladstone Park throws it back with a weekend packed with live music, contests, and family fun. Sing along with bands like Todd & the Ten Pins, 7th Heaven, and Magnetic Wave, while the fest also hosts a Miss Throwback pin-up contest, a pet costume parade, and a classic car show. Kids can hit the carnival rides, adults can browse arts and crafts vendors, and everyone can join in honoring first responders at the Heroes Celebration. It’s part block party, part time machine, and all about community.
Date: September 5-7
Time: Fri 4PM-10:30PM; Sat 10AM-10:30PM; Sun 11AM-8PM
Cost: $5
Location: Gladstone Park, 6030 N. Milwaukee Ave.
More Info: throwbackmusicfest.com
