Chicago Blues Festival | Millennium Park (6/8-11)
Take advantage of this free, three-day soulful festival this June. Although the line-up has yet to announce, the Chicago Blues Festival never fails to fill Millennium Park. Both top-tier and up-and-coming blues musicians are to perform, so join the rest of the city in attending the largest free blues festival in the world!
Windy City Smokeout | West Loop (7/13-16)
This renowned Chicago festival is coming back with a bang! There is simply no better combination than good music and barbecue, which this event has proved time and time again. This year, though, they are outdoing themselves. Windy City Smokeout’s 2023 lineup has led Chicagoans to sell out all the 4-day passes in a matter of weeks. There is no need to fret, though! Single-day passes are still available, so your chance to see electrifying performances by Zach Bryan, Darius Rucker, and Zac Brown Band remains intact! Don’t wait to get your hands on tickets, as the demand is vigorous.
Heatwave Music Festival | Northerly Island (6/10-11)
Spend your second weekend of June losing yourself to the music at Heatwave Music Festival. GRYFFIN, Loud Luxury, Malaa, GRiZ, Kx5, and Tiësto are only a handful of highlights on the lineup. Their fabulous melodies will pair well with the picturesque view at Northerly Island, so grab your tickets here!
Chicago Jazz Festival | Millennium Park (8/31-9/3)
Pay homage to one of the city’s most cherished art forms at The Chicago Jazz Festival. This event is a Labor Day weekend tradition that shows local talent alongside national and international artists. Musicians such as Henry Threadgill and Zooid, Bill Frisell, William Parker and his quintet, Miguel Zenón, and Linda May Han Oh have performed in recent years. Waltz into Millennium Park for free at the end of August and listen in on the magic!
World Music Festival Chicago | Chicago Cultural Center (9/22-10/1)
The presence of music is among cultures across the world. At the World Music Festival, this shared attraction is present through showcasing award-winning artists from around the globe. This festival creates a stirring patchwork of diverse instruments, voices, melodies, and dances for audiences, and it’s all for free!
Lollapalooza | Grant Park (8/3-6)
The best way to end a Chicago summer is with Lollapalooza. One last booming celebration under the blistering Chicago sun is essential, especially this year. Artists such as Billie Eilish, Kendrick Lamar, The 1975, Lana Del Ray, Maggie Rogers, and Odesza will be performing throughout the fantastical weekend. Check out the schedule here.
Food & Drink Festivals
Lincoln Park Greek Fest | Lincoln Park (6/2-4)
The St. George Greek Orthodox Church and Lincoln Park Greek Community are hosting the Lincoln Park Greek Fest. This festival offers everything a summer event should: food, music, drinks, and inviting culture. Regardless of your heritage, the fest promises that all attendees will be proudly Hellenic for one day as they experience the open arms of Greek culture.
Chicago Food Truck Festival | South Loop (7/29-30)
Head over to the South Loop during your last week of June to witness the glorious Food Truck Festival. This is the event’s 10th year, so the vendors are essentially seasoned professionals. Over the years, patrons have fallen weak for this cooking, so get your tickets here! Support local businesses, discover new restaurants, and devour delicious food!
Sangria Fest | East Village (8/19-20)
Quench your thirst under the blistering August sun at Sangria Fest! Thousands of glasses will fill with diverse, fruity flavors created by local mixologists. There will be a Paint & Sip lounge, as well as live music and food stations! This event is beloved by many and the perfect place for a final cheers to summer!
Taste of Chicago Grant Park (9/8-10) | Humboldt Park (6/24) | Pullman Park (7/15)
This list would not be complete without the biggest outdoor food festival in the world. The Taste of Chicago has been a summertime tradition for more than 40 years, and it is no wonder why. The “tastes” of this event do not end at the Chicago border, but instead are heavily influenced by the international nature the city hosts. All kinds of cuisines will be present at Taste of Chicago, so mark your calendars today to try them all out!
Art & Film Festivals
57th Street Art Fair | Hyde Park (6/3-4)
This June, attend the oldest juried fair in the Midwest! This event houses artists of glass, jewelry, photography, leather, painting, wood, sculptures, printmaking, and more. You’re guaranteed to find one-of-a-kind materials for yourself or loved ones, so mark your calendars today!
Wells Street Art Festival | Old Town (6/10-11)
This highly-anticipated neighborhood tradition is returning in June! International artists, live entertainment, kid-friendly areas, and delectable food and drinks will be offered. From woodworking and jewel-crafting to painting and sculpting, Wells Street will fill with various creations that both inspire and attract visitors!
Art Festival | Lake Street and Michigan Avenue (7/14-16)
Take a walk down to Michigan Avenue to experience the 15th Annual Millennium Art Festival! This event has a tendency to attract all those who pass, for it hosts all sorts of art! Ceramics, paintings, furniture, food, music and more will be at this patchwork festival. Get inspired by amateur artists and support the nature of creativity by entering, for free!
Indie Horror Film Festival | Chatham (8/26)
Horror in August? The answer is yes. There is never an unfitting time to experience independent film festivals, regardless of the genre! This event has consistently impressed audiences over the last decade, and it will continue to do so this year with vibrant, international screenings! Ink your calendars and experience the wonders of independent filmmaking at Cinema Chatman.
Written by Bridget McGann