Festivals in Chicago: A Comprehensive Guide

Whether you’re an architecture enthusiast, a music lover, or a foodie, Chicago’s festival scene has something for everyone. The festival season, lasting from the first hint of warm weather to the beginning of autumn, showcases over 400 neighborhood celebrations alongside numerous multi-day events. Below are some of the most exciting Chicago festivals.

Find out what’s brewing during Illinois Craft Beer Week

In mid-May, craft beer enthusiasts revel in a week-long celebration across Illinois. Breweries, bars, and restaurants partake in this exciting event, featuring hundreds of activities such as unique beer pairings, rare tappings, and spirited performances. One highlight in Chicago is Beer Under Glass, where over 100 breweries come together to share samples amid the lush greenery of the Garfield Park Conservatory.

Get sauced at Mole de Mayo

Among the myriad of street festivals that paint Chicago in color from spring to fall, Mole de Mayo, held in late May in Pilsen, truly shines. This festival celebrates local flavors, offering delectable street food like tacos and pambazos, while the star of the event is the rich mole sauce. Attendees can sample culinary creations from multiple neighborhood restaurants. After voting for their favorite, guests are treated to impressive entertainment, including traditional performances and lucha libre wrestling.

Rejoice in the written word at Printers Row Lit Fest

During a two-day event in June, more than 150,000 bibliophiles converge on S Dearborn St, also known as Printers Row. This literary festival features thousands of books for sale, readings by acclaimed authors such as Marilynne Robinson and Jonathan Safran Foer, along with entertaining activities for children, such as storytelling sessions.

2017 blues fest in Millennium Park — Huge crowds gather in Millennium Park’s Pritzker Pavilion each summer for Blues Fest © City of Chicago

Boogie down to Chicago Blues Festival

Every June, as the city inspires creativity, the Chicago Blues Festival attracts half a million music lovers to Downtown. Fans gather with their picnic baskets to enjoy sounds of iconic guitar riffs and blues melodies. This festival is recognized as the largest free blues festival in the world, celebrating the city’s rich musical legacy, which has featured legendary artists such as B.B. King and Buddy Guy.

Dig into chef-created bites at Taste of Randolph

June brings a culinary spectacle at this food festival in the West Loop, where chefs showcase their best creations. Expect innovative takes on classic comfort food items like meatballs and fried chicken, prepared by celebrated establishments such as Roister and Monteverde. This event not only showcases exceptional food but also hosts a lineup of live music, enhancing the overall experience for attendees.

Get down with the cool kids at Pitchfork

Indie-rock fans flock to the Pitchfork Music Festival for its eclectic mix of alternative and emerging talent. The event, held in Union Park, offers a vibrant ambiance where an artsy crowd can explore unique merch stalls while enjoying performances from popular acts such as Chance the Rapper and LCD Soundsystem.

woman performer at Lollapalooza — Phantogram takes a bow at Lollapalooza © Charles Reagan Hackleman / Lollapalooza 2017

Turn it up to 11 at Lollapalooza

The famed Lollapalooza is one of Chicago’s most anticipated events, featuring over 130 bands across eight stages for four exhilarating days. With renowned artists like Paul McCartney and Lorde taking the stage, attendees can rock out, enjoy diverse food options including gourmet street vendors, and participate in various exciting activities.

Dance in the streets at Northalsted Market Days

As summer sizzles, Chicago’s LGBTQ neighborhood bursts into life with the Northalsted Market Days. This six-block street festival welcomes revelers of all backgrounds to enjoy a day filled with music, craft vendors, and unforgettable performances by beloved artists such as Gloria Gaynor.

Bid summer a swinging farewell at Chicago Jazz Festival

Kicking off Labor Day weekend, the Chicago Jazz Festival allows enthusiasts to relax in Millennium Park while enjoying smooth tunes from esteemed musicians. With decades of tradition, this festival has showcased legends like Miles Davis, making it a pinnacle event for jazz lovers as summer winds down.

a man photographs the modernist organ in the Seventeenth Church of Christ, Scientist — Open House Chicago gives an insider’s view of buildings normally closed to the public, like the modernist Seventeenth Church of Christ, Scientist © Marcin Wichary

Get a new view of the city at Open House Chicago

In October, the Open House Chicago invites visitors to explore more than 200 unique buildings designed to inspire and engage. This free festival, coordinated by the Chicago Architecture Foundation, showcases stunning sites that typically remain inaccessible, revealing hidden gems throughout the city.

Put on your smarty pants at the Chicago Humanities Festival

For two enlightening weeks in November, the city hosts an eclectic mix of notable speakers at the Chicago Humanities Festival. Engaging discussions cover a wide range of topics from culture to social issues, featuring esteemed figures such as Ta-Nehisi Coates and Margaret Atwood. This event is not to be missed for those eager to deepen their understanding of contemporary themes.