CHICAGO — Whether you’re into tequila tastings, Swedish midsummer celebrations, or outdoor art fairs, there’s something for everyone in Chicago and the suburbs this weekend.
From June 13 through June 15, the city is packed with cultural festivals, culinary experiences, and free music events. Here’s your complete guide to what’s happening this weekend across the area:
Scottish Festival & Highland Games (Wheaton)
Location: DuPage County Fairgrounds, 2015 Manchester Rd., Wheaton
When: Friday, June 13 (1–10 p.m.) & Saturday, June 14 (9 a.m.–10 p.m.)
More info: chicagoscots.org
The 39th annual Scottish Festival & Highland Games will bring a weekend of Scottish traditions, live music, athletic competitions, and bagpiping to the western suburbs. Hosted by the Chicago Scots, this family-friendly event also offers whisky tastings and cultural exhibitions.
Zoo Uncorked: Tequila and Tails (Brookfield Zoo)
Location: Brookfield Zoo, East Mall & Pavilions
When: Saturday, June 14, 6–9 p.m.
Tickets: brookfieldzoo.org
This adults-only (21+) event features premium tequila pairings, Hispanic-inspired cuisine, and access to animal habitats like the Big Cat Walkway. Guests can sip and stroll under the stars while enjoying a lively summer vibe.
Andersonville Midsommarfest
Location: 5400 N. Clark St., Chicago
When: June 13–15
Details: andersonville.org
A Chicago staple, this Swedish-inspired street fest transforms Clark Street into a celebration of music, dance, and community spirit. Look for traditional costumes, folk dancing, and local vendors all weekend long.
Taste of Randolph (West Loop)
Location: Randolph St. between Peoria and Racine
When: June 13–15
Info: tasteofrandolph.org
The 28th annual Taste of Randolph returns with food from top West Loop restaurants and live performances across three stages. Expect a mix of local and national acts in one of Chicago’s most vibrant dining districts.
Old Town Art Fair
Location: 1763 N. North Park Ave., Chicago
When: June 14–15
Learn more: oldtownartfair.org
Now in its 75th year, this iconic fair features 200+ artists, a garden walk, live music, and family-friendly activities. A great stop for art lovers and anyone seeking a slower-paced outing.
Wells Street Art Festival
Location: Wells St. between North Ave. and Division St., Chicago
When: June 14–15
Details: chicagoevents.com
With 130 juried artists, this fair showcases unique fine arts, food vendors, and entertainment across two days. A perfect pairing with the nearby Old Town Art Fair.
Grant Park Music Festival – Opening Weekend
Location: Jay Pritzker Pavilion, Millennium Park
When: Kicks off this weekend; runs all summer
Festival info: grantparkmusicfestival.com
One of the nation’s only free outdoor classical music series, this festival opens its 10-week run. Bring a picnic and enjoy symphonic sounds under the skyline.
“The Terminator” in Concert (Auditorium Theatre)
Location: 50 E. Ida B. Wells Dr., Chicago
When: Friday, June 13, 7:30 p.m.
Tickets: auditoriumtheatre.org
The Chicago Philharmonic performs the original score live as the cult classic film plays on the big screen — a cinematic experience unlike any other.
Comedian Sandra Bernhard at Park West
Location: 322 W. Armitage Ave., Chicago
When: Saturday, June 14, 8 p.m.
Tickets: jamusa.com
After a recent heart surgery, actress and comedian Sandra Bernhard returns to the stage for her national tour — raw, hilarious, and unforgettable.
Oscar Peterson’s “Africa Suite” at Symphony Center
Location: 220 S. Michigan Ave., Chicago
When: Friday, June 13, 8 p.m.
Details: cso.org
A rare live performance of Peterson’s jazz tribute to Nelson Mandela and the anti-apartheid movement. Features an all-star jazz ensemble.
CTA Concerts This Weekend
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KEM – R&B Soul Artist
Country Club Hills Theater | Friday & Saturday, 7 p.m.
Info: cchtheater.com -
Counting Crows – Grammy-Nominated Rock Band
Ravinia Festival, Highland Park | Friday, 7 p.m.
Details: ravinia.org
Reminder for Weekend Travelers
Expect extra crowding and possible reroutes around major festival zones, including Randolph Street, Wells Street, and Millennium Park. Plan accordingly or use the CTA’s trip planner to map your route in advance.
Want More Weekend Ideas?
Whether you’re looking for something romantic, family-friendly, or just free — stay tuned for our upcoming Monday preview of next weekend’s Chicago events calendar.
What’s Your Favorite Chicago Summer Event?
Tell us your go-to festival, food stop, or concert venue in the comments at ChicagoSuburbanFamily.com or tag us on social.
