Spring has sprung across Chicagoland and there many exciting events to fill your calendar! From family events to date night activities, there’s something for everyone—here are a few of our top picks to check out this weekend.
Keep it Smooth at June Jazz
Settle in for a summer evening on the lawn at Elmhurst University’s June Jazz concert, now in its 29th year. This free, outdoor performance features acclaimed musicians Byron Stripling, Bobby Floyd, Sydney McSweeney, and Jim Rupp. Held on the university’s scenic arboretum campus, the show invites guests to bring lawn chairs, picnic baskets, and blankets to soak in the music.
Date: June 14
Time: 6:30PM
Cost: Free
Location: Elmhurst University, 190 Prospect Ave, Elmhurst
More Info: elmhurst.edu
Sip and Stroll at Tequila & Tails
This beloved event returns for a 21+ after-hours experience that mixes cocktails with conservation. Alongside signature drinks, guests can join animal chats, meet surprise ambassadors, and explore exhibits by moonlight—plus enjoy live music, photo booths, and lawn games. Different ticket tiers offer à la carte or all-inclusive drinks, including a mocktail option. Food add-ons feature curated pairings like brisket tacos, mango ceviche, and key lime parfaits. Whether you’re here for the tails or the tequila, it’s a wild night out with a cause.
Date: June 14
Time: 6PM-9PM
Cost: $40+
Location: Brookfield Zoo, 3300 Gold Rd, Brookfield
More Info: brookfieldzoo.org
Connect and Reflect at the Juneteenth Community Cookout
Oak Park’s Juneteenth Community Cookout blends music, culture, and community with a lineup of performances, family activities, and local Black-owned food vendors. Enjoy soul, funk, and dance music from J Grant Experience and DJ Camo, or watch the Jesse White Tumblers and Kuumba Kids Cultural Showcase in action. From BBQ and vegan bites to ice cream and face painting, there’s something for everyone.
Date: June 14
Time: 11AM-3PM
Cost: Free
Location: Village Hall, 123 Madison St, Oak Park
More Info: oak-park.us
Celebrate Puerto Rican Pride at Fiestas Patronales Puertorriqueñas
This festival brings the sounds, flavors, and energy of Puerto Rico to Humboldt Park for a four-day cultural takeover. The weekend kicks off with the annual Puerto Rican People’s Parade, followed by a sprawling festival with more than 25 carnival rides, 150 vendors, and live music all day. Expect classic Latin food, drink tastings, giveaways, and a full-on Ferris Wheel with a view.
Date: June 13-15
Time: Fri 3PM-10PM; Sat & Sun 12PM-10PM
Cost: $17.50+
Location: Humboldt Park, 2800 W Division St
More Info: puertoricanfest.com
Go All Out at Midsommar Fest
Midsommarfest is Andersonville’s beloved street festival and a can’t-miss for anyone who loves summer crowds, live music, and Scandinavian spirit. Along with food and drinks from local vendors, the weekend is stacked with multiple performance stages, drag shows, craft booths, and a dedicated kids’ zone.
Date: June 13-15
Time: Fri 5PM-10PM; Sat 12PM-10PM; Sun 12PM-9PM
Cost: $10 Suggested Donation
Location: Clark St from Foster Ave to Gregory St
More Info: andersonville.org
Have a Feast at the Taste of Randolph
Taste of Randolph is back in the West Loop, pairing its restaurant row roots with a full slate of music and local flavor. Expect curated bites from some of the neighborhood’s most popular spots, plus three stages of live acts that make the fest feel like a block party-meets-concert. It’s one of the city’s tastiest events of the season.
Date: June 13-15
Time: Fri 5PM-10PM; Sat & Sun 12PM-10PM
Cost: $10 Suggested Donation
Location: Randolph St from Peoria St to Racine Ave
More Info: tasteofrandolph.org
Find Your Favorite Piece at the Old Town Art Fair
This art fair turns the neighborhood into an open-air gallery with more than 200 artists from across the country. Beyond paintings and prints, visitors can take a self-guided Garden Walk, browse handmade goods, catch live tunes, or swing by the food court and family zone. A portion of proceeds supports community nonprofits.
Date: June 14-15
Time: Sat 10AM-7PM; Sun 10AM-7PM
Cost: $10 Suggested Donation
Location: Old Town Triangle Center, 1763 N Park Ave
More Info: oldtownartfair.org
Head to the Wells Street Art Festival
Wells Street Art Festival celebrates its 50th anniversary with a lineup of over 130 juried artists, local eats, and music in the heart of Old Town. The historic stretch between North Avenue and Division will also feature interactive booths, pop-up vendors, and family-friendly activities throughout the weekend.
Date: June 14-15
Time: Sat 10AM-10PM’ Sun 10AM-9PM
Cost: $10 Suggested Donation
Location: Wells St from North Ave to Division St
More Info: wellsstreetartfest.us
