Windy City Boat & Yacht Show

June 12–14  |  Burnham Harbor, South Loop (459 E 18th Dr)

Set against the backdrop of Lake Michigan and Chicago's skyline, this is the Great Lakes' premier in-water celebration of boating. Expect over 100 boats up to 75 feet, shoreside exhibits, and the latest in marine technology and gear — from new debuts to premium brokerage listings.

Andersonville Midsommarfest

June 12–14  |  Clark Street from Foster to Gregory

Rooted in Swedish tradition, this three-day neighborhood celebration features 50 musical acts across four stages and more than 200 vendors. Food, art, shopping, and community — all in one of Chicago's most beloved neighborhoods.

Wells Street Art Festival

June 13–14  |  Old Town (Wells Street from North Ave to Division St)

127 talented artists, live music, and festival food fill the streets of Old Town for a full art-filled weekend. Check out the music lineup and hands-on activities for the whole family.

Family Fun Fur-Iday

June 12  |  7:00 PM  |  Lincoln Park Zoo (2001 N Clark St)

End the week on the wild side. This family-friendly after-hours zoo experience includes a live DJ, animal chats, games, and more — a perfect summer evening with the kids.

Puerto Rican People's Parade

June 13  |  12:00 PM  |  Humboldt Park (Division & Clark)

Bomba y Plena performances, vibrant celebrations, and Parrandas flowing right into the park. A powerful community tradition in the heart of Humboldt Park.

Jeremy Piven — Stand-Up Comedy

June 12–14  |  IMPROV Chicago, Schaumburg (5 Woodfield Mall)

The 2x Golden Globe and 3x Emmy Award winner best known for Entourage brings his touring stand-up show to Schaumburg. A rare chance to see a household name flex a different kind of comedic muscle live.

Sonny Acres Pro Rodeo & Stampede

June 12–14  |  Sonny Acres Farm, West Chicago (29W310 North Ave)

World-class rodeo competition meets classic farm fun — bull riding, bucking horses, amusement rides, pony rides, a petting zoo, live music, and great food all in one lively country setting.

Woodstock Pride Fest

June 12–14  |  Woodstock Square & Beyond (121 Van Buren St)

This year's theme is "Love Is Always in Focus." An expanded weekend of celebration, music, and community, with the beloved Pride Parade closing out the weekend on Sunday, June 14.

Skokie's Juneteenth Celebration

June 14  |  12:00 PM–4:00 PM  |  Oakton Park, Skokie (4701 Oakton St)

This year's theme: "Lift as We Climb." Opening ceremony, speakers, performances, vendors, and a DJ close out the afternoon in a celebration of community and culture.

Glenview Summer Fest

June 13  |  9:00 AM–10:00 PM  |  Lehigh Avenue & Jackman Park, Glenview

Over 100 local businesses, a kids' area with balloon artists and face painting by day — and live music, local eats, and cold drinks after sunset. One of the North Shore's best summer traditions.

Concerts in Your Park

June 14  |  7:00 PM–8:30 PM  |  Three Meadows Park, Naperville (1320 Brittany Ave)

Bring your lawn chairs and blankets for a free evening of live outdoor music. A perfect Sunday wind-down with friends, family, and neighbors.