Every weekend during the summer, Chicago comes alive with festivals, ranging from neighborhood celebrations to huge events that spotlight the city’s ethnic and cultural diversity. We’ve combed through the listings and found these 11 festivals. Admission to all, except for the Windy City Smokeout, is free, although some have a suggested donation.
Maifest
Spring’s counterpart to Oktoberfest, Maifest fills Lincoln Square with German culture from May 29 – June 1. Enjoy two stages of traditional music and dance while feasting on bratwurst, leberkaese and beer. The festival is at 4521 N. Lincoln Avenue in Lincoln Square, across from the Old Town School of Folk Music. Take the Brown Line to Western and follow the aroma of grilled sausages.
Chicago Blues Festival
The 41st Chicago Blues Festival celebrates the Windy City’s musical heritage from June 5 – 8. It begins at Bridgeport’s historic Ramova Theatre with panel discussions and a headlining set by 91-year-old legend Bobby Rush. The festival then moves to Millennium Park, with three stages of local and national blues stars. Highlights include a tribute to B.B. King, C.J. Chenier and the Red Hot Louisiana Blue Band, and performances saluting women in blues and Chess Records. Chicago’s living legend and civil rights icon Mavis Staples, closes out the festival on June 8.
Magnificent Mile Art Festival
The area surrounding the former John Hancock Center transforms into a free art gallery at the juried Magnificent Mile Art Festival. Featuring work from over 60 artists in numerous disciplines, the event will take place June 21 – 22 from 10 a.m. to 5 p.m. Returning award-winning artists include jewelry-maker David Alvarado and painter Val Fischer.
Chicago Pride Fest
The weekend before the Pride Parade (June 21 – 22), Pride Fest fills Halsted St. from Addison St. to Grace St. with a celebration of LGBTQ+ culture. Its three stages will feature live music, drag performances, DJs and dancing, with more than 150 food and merchandise vendors lining the street. A suggested donation of $20 supports the performers, workers and Northalsted organizations.
Windy City Smokeout
Get all the country vibes you need without ever leaving Chicago at the Windy City Smokeout. Taking place outside the United Center from July 10 – 13, the days will be full of country music and barbecue from the best local and national pitmasters. Headliners include Old Dominion, Megan Moroney and Kane Brown. Wristbands can be purchased online with different level options and even a Saturday BBQ brunch.
Lincoln Park Summer Wine Fest
Enjoy all the wonderful views of a Chicago summer at the Lincoln Park Summer Wine Fest. Held at the Lincoln Park Zoo on the evening of July 25, guests can enjoy 20 tastings from various winemaking regions and participating wineries including Kim Crawford Wines and Benziger. Also included with the purchase of a ticket is a guided tour with horticulture experts and live music.
Chinatown Summer Fair
Take the Red or Green Line to Cermak Rd. for the Chinatown Summer Fair. Put on by the Chicago Chinatown Community Foundation, the annual tradition brings more than 40,000 people to a celebration of Asian culture. Chinatown Square’s main stage will be filled with traditional music, dance and kung fu demonstrations, and you’ll be able to sample food from Chinatown’s many restaurants. The two-day festival kicks off on July 26 with a lion dance procession up Wentworth Ave.
Printer’s Row Art Fest
The Printer’s Row Art Fest is returning for its sixth year to bring more creativity and inspiration to Printer’s Row Park in the South Loop. From Aug. 9 – 10, more than 90 artists will showcase and sell their works. Find a new piece of handcrafted jewelry or a painting or photograph for your home.
Chicago Air & Water Show
Head to the lakefront from Aug. 16 – 17 for the 64th Air & Water Show. An annual summer highlight, the weekend showcase of the death-defying stunts of civilian and military pilots, including the Blue Angels, over Lake Michigan. The best location to view the excitement is at North Avenue Beach, but anywhere along the lake from Navy Pier to Fullerton Pkwy. will provide exceptional views, and you can reserve spots at many rooftop restaurants. But if you’re going to the beach, be sure to get there well in advance of the 10:30 a.m. start time. More than 1 million people attend the Air & Water Show annually.
Chicago Jazz Festival
The world’s largest free jazz festival, the Chicago Jazz Festival takes over Millennium Park over Labor Day Weekend. Three stages in the park will showcase local, national and international jazz musicians starting on Aug. 28. Headliners at Pritzker Pavilion include Grammy-winner esperanza spaulding, New Orleans trumpet great Kermit Ruffins and Buena Vista Social Club guitarist Eliades Ochoa.
Taste of Chicago
Get all the flavors of the city in one place at Taste of Chicago. Founded in 1980, this foodie festival takes over Grant Park from Sept. 5 – 7. Restaurants range from local institutions like Lou Malnati’s Pizzeria, the Original Rainbow Cone and Harold’s Fried Chicken to neighborhood ethnic spots from the North, South and West Sides.
