Bookworm? Architecture buff? Indie rocker? No matter how you roll, Chicago’s got a festival for you. Each festival season – which stretches roughly from the first suggestion of mild temps until the first threat of flurries – brings over 400 neighborhood shindigs alone, not to mention a host of multi-day events keyed to interests from hoppy brews to electric blues. Here, 11 of the best Chicago fests.
Beer Under Glass, part of Illinois Craft Beer Week, is a tasting event held at the lush Garfield Park Conservatory © Illinois Craft Brewers Guild
Find out what’s brewing during Illinois Craft Beer Week
Mid-May is heaven for hopheads around Illinois: for one intoxicating week, breweries, bars and restaurants around the state celebrate the sudsy stuff with hundreds of events like pairing dinners, rare beer tappings, and even booze-fueled performance art. Here in Chicago, the annual highlight is Beer Under Glass, when more than 100 area breweries convene to pour samples of their wares amidst the tropical greenery of the Garfield Park Conservatory’s soaring greenhouses.
Mole Fest in Pilsen is a music- and food-filled annual party © Troy Heinzeroth
Get sauced at Mole de Mayo
Of the hundreds of neighborhood fests that take over Chicago’s streets from spring through fall, this one, held in late May in the predominantly Mexican community of Pilsen, stands out for fantastic fare with a distinctly local flavor. Street eats like tacos and pambazos perfume the air with earthy smoke, but the star of the show is the complex, hearty sauce that gives the event its name. Over a dozen area restaurants serve up their take. Vote for your favorite, and then grab a michelada and check out the diverse entertainment, including traditional Chinelos dancers and high-flying lucha libre wrestling.
Rejoice in the written word at Printers Row Lit Fest
For two days in June, over 150,000 bibliophiles swarm S Dearborn St, aka Printers Row, for this literary event which features thousands of rare and not-so-rare books for sale and readings from big-name authors like Marilynne Robinson and Jonathan Safran Foer, plus kid-centric events like storytelling. Fill a bag as you browse the booths on the very street where printing companies used to cluster back in the day when Chicago was a publishing hub.
Huge crowds gather in Millennium Park's Pritzker Pavilion each summer for Blues Fest © City of Chicago
Boogie down to Chicago Blues Festival
When half a million people stream Downtown in early June with blankets and picnic baskets in tow, it's kickoff time for Blues Fest. Fans flock to hear guitar notes slide, bass lines roll and fret-bending bands work their mojo. It's the largest free blues gig in the world – a fitting legacy for the city that electrified the genre. Since its 1984 inception, the festival has welcomed no lesser lights than B.B. King, John Lee Hooker and Koko Taylor, and local axe-man Buddy Guy is a frequent flyer.
Dig into chef-created bites at Taste of Randolph
With apologies to Chicago’s other food-centric street festivals, it’s this weekend-long June shindig that boasts the real culinary bonafides, unfolding as it does in the buzzy West Loop, home to many of the city’s most celebrated kitchens. Expect creative takes on casual fare like meatballs and fried chicken from hot spots such as Grant Achatz’s Roister and Sarah Grueneberg’s Monteverde, plus a respectable music lineup that in years past has featured acts like Atlas Genius, Dawes and Dinosaur Jr.
Get down with the cool kids at Pitchfork
Bespectacled indie-rock fans get giddy for the taste-making line-up of alternative and emerging acts at the Pitchfork Music Festival. The young crowd – in thrift store sundresses and Converse high tops, tie-dyed shirts and jean shorts – roams between the three main stages in offbeat Union Park, with pit stops to buy vinyl, screenprints and Etsy-worthy handicrafts in between. Recent headliners include Chance the Rapper, Sufjan Stevens and LCD Soundsystem.
Phantogram takes a bow at Lollapalooza © Charles Reagan Hackleman / Lollapalooza 2017
Turn it up to 11 at Lollapalooza
The super-sized rock festival amps up Grant Park like no other bash, with 130+ bands getting loud on eight stages. For four full days guitars thrash, lights spin and the audience dances into a sweaty, arm-flailing frenzy. The likes of Paul McCartney, Radiohead, Lorde and Outkast have taken their turns as headline acts. Beyond rock and roll, Lolla has tents for video game playing, eco-friendly shopping and chowing down on lobster corndogs (tattooed TV chef Graham Elliot curates the food vendors).
Dance in the streets at Northalsted Market Days
Boystown lets loose when summer's heat peaks. For this six-block street party, revelers gay and straight alike prowl incense-wafting craft vendors along Halsted Street in the heart of Chicago's LGBTQ neighborhood. Drag queens in feather boas, Twister games played in the street and disco divas on the main stage (Gloria Gaynor! Olivia Newton-John!) are a sure bet.
Bid summer a swinging farewell at Chicago Jazz Festival
Jazz Fest anchors the city's Labor Day festivities. Devotees chill in chairs on Millennium Park's lawn or in the marble confines of the Chicago Cultural Center, and pretend the prominent musicians aren't blowing the last notes of summer on their horns. Well into its fourth decade, Jazz Fest has seen Miles Davis, Dave Brubeck, Charlie Haden and their like bebop into the night.
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
From gilded theaters to hyper-modern high rises, over 200 buildings citywide throw open their doors for free tours during this weekend-long October festival, coordinated by the Chicago Architecture Foundation. Because they’re tucked off the beaten path or usually off limits to the public, many of the sites on the roster would normally fly under the radar; consequently, they reveal a side of Chicago that visitors – or, for that matter, locals – don’t normally see.
Put on your smarty pants at the Chicago Humanities Festival
For two weeks each November, nearly 100 culture makers of all stripes (think prominent social critics such as Ta-Nehisi Coates and novelists like Margaret Atwood, politicians like Al Gore and musicians such as Elvis Costello) converge upon Chicago for this brainy festival, delivering lectures, performances, and exhibits keyed to the year’s appointed theme at venues across the city. The collective result is a prismatic view of topics as wide-ranging as journeys, America and laughter.
Get more travel inspiration, tips and exclusive offers sent straight to your inbox with our weekly newsletter.