Chicago’s Most Distinctive Summer Festivals and Events

Street festivals are an integral part of Chicago summers. The basic premise is that a neighborhood closes a few blocks of its major street to traffic for a weekend and fills it with food and merchandise vendors, two or three stages for live music, and activities for children. They’re a great opportunity to spend the day exploring other neighborhoods and supporting local businesses while enjoying the outdoors.

By Dave Lifton (@daveeatschicago)

As fun as they are, many of them are indistinguishable from each other, with near-identical food options and musical lineups. These, however, all have something different about them. If you’re coming to Chicago during any of these weekends and are looking for something distinctly Chicago, check them out.

The West Central Association hosts its inaugural West Loop Wine Walk on June 6^th from 4 – 7 p.m. Participants can sample wine with small bites at 14 businesses on Madison St., including Crosstown Fitness and Madison Street Books. A $55 ticket includes a tasting glass, plus discounts at the stops, raffles, and other gifts. Starting locations will be staggered to ensure that the afternoon flows as smoothly as possible.

Since 2004, the Full Moon Jam has filled various Chicago parks throughout the summer with evenings devoted to drumming and fire-spinning. This year’s schedule starts at Foster Beach on June 11^th before moving to Evanston’s Arrington Lagoon (June 20), Winnemac Park (July 4), Foster Beach (July 10^th), Rainbow Beach (Aug. 8^th) and Palmisano Park (Sep. 8^th). Each jam starts at sunset and goes until 10 p.m. There is no admission fee.

Full Moon Fire Jam

From June 12^th-15^th, several locations throughout downtown will host the Windy City Paranormal Festival. In addition to presentations by leading paranormal researchers and live podcast recordings, events include happy hours in the Spookeasy, the BOO!-lesque show, Paranormal Pictionary, and the Haunted ‘80s Prom. As an add-on, visitors can tour Graceland Cemetery on Sunday morning.

Vegandale, North America’s touring celebration of an animal-free lifestyle reaches Grant Park’s Butler Field on June 21^st-22^nd. Attendees will be able to buy food and drinks from roughly 100 vendors from around the world, including London’s famous Temple of Seitan. Enjoy live music and DJs, and visit the interactive art gallery for Instagram-friendly photo opportunities.

The Chicago Naked Bike Ride isn’t a festival, but it is an annual event that draws media attention. It’s exactly what it claims to be, a clothing-optional trek through city streets designed to promote body positivity and independence from fossil fuels. This year’s version takes place on July 12^th. Full details, including the route, are typically not revealed until the day before. However, the 2024 version was a 14-mile ride that took place from 8 p.m. – midnight.

The craft beer scene on the North Side gets its own festival on July 19^th-20^th. Held in Malt Row, a former industrial corridor that now houses eight brewers and one distillery, Ravenswood on Tap allows you to sample their products with 5 oz. tasting pours or 12 oz. full pours. In addition to the beer, enjoy local original bands, demonstrations of swordplay, and axe-throwing.

The city’s Far East community takes the spotlight from July 26^th-27^th with the Chinatown Summer Fair. It kicks off with a lion dance procession, after which the stage at Chinatown Square will be filled with performances of Asian music and dance, kung fu demonstrations, and other examples of Chinese culture. And, of course, plenty of food from local restaurants.

If you’re in town for Labor Day Weekend (Aug. 29^th–Sept. 1^st), be sure to visit Jefferson Park for Taste of Polonia It’s the largest celebration of Polish culture in the U.S., with more than 30 food vendors selling Polish classics like pierogi, kielbasa, and potato pancakes, plus polka bands and dancing.

The city’s book-loving community will come together Sept. 6^th-7^th for the Printers Row Lit Fest. More than 100 booksellers will line the streets of Printers Row, and 100 authors will take part in discussions and panels. This year’s headlining speaker is Sandra Cisneros, an award-winning Chicago-based poet and novelist.

Lastly, Chicagoans’ fascination with St. Patrick’s Day is well-documented. We love it so much that we celebrate it twice. Manny’s, the city’s famous Jewish deli in the South Loop, will go green on Sept. 20^th-21^st for the Halfway to St. Patrick’s Day Corned Beef Festival. The Chicago River won’t be dyed, but Manny’s will serve its much-loved corned beef and other Irish dishes, with traditional Irish music and dance, plus plenty of activities for the children.

The author of this article will not be taking part in the Naked Bike Ride, but will go to any Chicago street festival where Dancing Queen: An ABBA Salute performs.