Andersonville Midsommarfest
Location: Clark St between Foster & Catalpa
Dates: June 13–15
Description: A Swedish-inspired street festival with music, food, crafts, and dancing in one of Chicago’s most charming neighborhoods.

Old Town Art Fair
Location: Old Town Triangle Historic District
Dates: June 14–15
Description: A juried art fair featuring over 200 artists, garden walks, live music, and delicious food.

Puerto Rican Festival & People’s Parade
Location: Humboldt Park, Division St
Dates: June 12–15
Description: A celebration of Puerto Rican heritage with food, music, dancing, and a lively parade.

Make Music Chicago
Location: Citywide
Date: June 21
Description: A citywide music festival where anyone can perform, celebrating the global Fête de la Musique.

Vegandale Festival
Location: Grant Park, 337 E Randolph St
Dates: June 21–22
Description: A festival for vegans and the vegan-curious featuring plant-based food vendors, music, and art.

Wells Street Art Festival
Location: Wells St between North Ave & Division St
Dates: June 14–15
Description: A vibrant art festival with 250+ artists, live music, and food vendors in historic Old Town.

Swedish Days Festival
 Location: Downtown Geneva, IL

 Dates: June 18–22
 Description: A family-friendly suburban festival with Swedish culture, parades, music, food, and carnival rides.

Rotary GroveFest
Location: Downtown Downers Grove, IL

Dates: June 19–22
Description: Live music, carnival attractions, food trucks, and crafts in a welcoming suburban downtown.

Lindsey Stirling
Location: Ravinia Pavilion, 418 Sheridan Rd, Highland Park, IL
Date: June 26
Description: The acclaimed violinist-dancer brings her electric live performance to Ravinia’s outdoor stage.

Hauser
Location: The Chicago Theatre, 175 N State St

Date: June 10
Description: A classical crossover cello concert from the famed member of 2Cellos.

Queens of the Stone Age
Location: Huntington Bank Pavilion, 1300 S Linn White Dr
Date: June 21
Description: Rock out at Northerly Island with the iconic alternative rock band on their summer tour.

Billy Strings
Location: Allstate Arena, 6920 Mannheim Rd, Rosemont, IL
Date: June 7
Description: Grammy-winning guitarist brings modern bluegrass to a massive live crowd.

Architecture River Cruise
Location: Departures from various river docks (e.g., Michigan Ave)
Description: One of the top-rated ways to learn about Chicago’s architectural legacy from the water.

Grant Park Music Festival
Location: Jay Pritzker Pavilion, Millennium Park, 201 E Randolph St
Dates: June 12–August 17
Description: Free, open-air classical music performances by the Grant Park Orchestra.

Magnificent Mile Art Festival
Location: North Michigan Ave between E Pearson & E Huron
Dates: June 21–22
Description: A premier art show on Chicago’s most famous shopping boulevard.

Adler at Night
Location: Adler Planetarium, 1300 S Lake Shore Dr
Date: June 11
Description: Evening exploration with interactive exhibits, shows, and stargazing.

Skydeck Chicago (Willis Tower)
Location: 233 S Wacker Dr
Description: Step out onto The Ledge, a glass box 1,353 feet in the air, with stunning views of the city.

360 CHICAGO Observation Deck
Location: 875 N Michigan Ave (John Hancock Center)
Description: Panoramic views of the skyline and lakefront, plus the adrenaline-pumping TILT attraction.