There’s so much going on in Chicago this summer, from concerts and festivals to parties and fairs! Read on for some of the best things to do and see around Chicago this summer!


  • Enjoy the Grant Park Music Festival, with multiple performances per week from June 13th to August 18th! Treat your ears to the finest in classical and symphonic music.
  • Enjoy art and entertainment related to area history in Rockport at the Old Canal Days Craft and Art Fair, going June 16th - 17th! Enjoy a carnival, parade, and wide variety of food vendors.
  • Kick it and rock out at the World’s Largest Block Party at the West Loop Gate from June 22nd - 23rd! Enjoy a weekend of fantastic music, food and fun.
  • Sate your sweet tooth at the Strawberry Festival in Long Grove, from June 22nd - 24th! Enjoy all things strawberry, from strawberry BBQ to a pie-eating contest.
  • Celebrate human sexuality and freedom at the Chicago Pride Parade on June 24th! The parade will wind through Uptown, Lakeview and Lincoln Park.
  • Get your sizzle on at the Chi-Town Hot Sauce Expo in Bridgeview from June 23rd - 24th! Sample a variety of zesty and tangy hot sauces dipped in your favorite festival foods.
  • Check out the Art Fair at the Chicago Botanic Gardens from June 30th through July 1st! Stroll and shop among 100 top artists along the Esplanade.
  • Bop to the performances of top hip-hop acts and rappers on Oakwood Beach at Mamby on the Beach from June 23rd - 24th! Headliners include Russ, Common and The Cold War Kids.


  • Check out the African and Caribbean International Festival of Life from July 6th - 8th in West Town! Enjoy music, food, entertainment and more geared towards promoting togetherness and equality.
  • Gorge on beer and BBQ at the Windy City Smokeout from July 13th - 15th in the Fulton River District! Enjoy performances from top country bands while you feast on BBQ and beer from the world’s best pitmasters.
  • Get your green on at the Irish-American Heritage Festival from July 6th - 8th in Mayfair! Enjoy traditional Irish food, music and entertainment.
  • Check out the Southport Art and Music Festival from July 14th - 15th in Lakeview! Check out art and music created by some of the region’s most up-and-coming artists.
  • Take your tastebuds south of the border... and then south some more at Colombian Fest from July 20-22 in Hermosa! Enjoy Colombian food, music and entertainment.
  • Have fun at the Square Roots Festival from July 13th - 15th in Lincoln Square! Enjoy food, music and entertainment that harkens back to Chicago’s classic days.
  • Embrace Chinese culture and check out the Chinatown Summer Fair in Chicago’s Chinatown! On July 15th, enjoy Chinese food, music and entertainment.
  • Take your tastebuds on a trip at the Taste of Lincoln Avenue from July 28th - 29th on Lincoln Avenue! food, music, entertainment, craft and retail vendors and more!
  • Chow down on your favorite Mexican food from July 20th - 22nd at the Tacos Y Tamales Festival in Pilsen! Enjoy a variety of mouthwatering Mexican food, art, and a beer garden.


  • Dance, dance, dance at the biggest musical festival of the year, Lollapalooza, from August 2nd - 5th in Grant Park. Headliners this year include The Arctic Monkeys, The Weeknd, Jack White and Bruno Mars. This is your best chance all year to catch your favorite bands!
  • Have a a-spicy meat-a-ball at the Little Italy Festa, August 2nd - 5th in Addison! Enjoy Italian food, music and entertainment and browse a variety of cultural displays and shops.
  • Free your inner Cuban at Festival Cubano, August 11th - 12th in Belmont Cragin! Enjoy Cuban food, music and entertainment, including performances by world-renowned Cuban bands!
  • Sample a variety of delectable foods, chat and make new friends, and have fun at the Near North Food Truck Social from August 11th - 12th! Sample food from hundreds of the Midwest’s finest food trucks in a fun social environment.
  • Enjoy perhaps the biggest collection of entertainment of any festival at Northalsted Market Days, August 11th - 12th in Lakeview! Enjoy the largest variety of food, music and entertainment of any street fair in the Midwest! This event is MASSIVE - good luck exploring it all!
  • Get down at the Slow&Low: Chicago Lowrider Festival, August 12th in Pilsen! Check out the illest of these classic cars on display.
  • Celebrate the best of Ukrainian culture at the Ukrainian Days Festival, August 25th - 26th in West Town! Enjoy the best in Ukrainian food, music and entertainment.
  • Get reaaaal cool at the Chicago Jazz Festival, August 30th through September 2nd in The Loop. Enjoy performances by the baddest of the famous Chicago jazz scene.