Taste of Chicago
This five-day food festival in Grant Park draws hordes for a smorgasbord of ethnic, meaty, sweet and local edibles – much of it served on a stick. Several stages host free live music, including big-name bands.
Illinois Craft Beer Week
In late May, hundreds of breweries, restaurants and bars around Chicago and further afield get in on this week-long celebration of the sudsy stuff, putting on events such as rare beer tappings and pairing dinners. Among the highlights is Beer Under Glass, a tasting extravaganza staged amid the tropical greenery of the Garfield Park Conservatory.
Chicago Architecture Biennial
Chicago has long been an architecture innovator (inventor of the skyscraper et al). This three-and-a-half-month event brings together designers from around the world for free exhibitions, tours and public programs.
Mole de Mayo
The food’s the star at this Pilsen street festival, especially the mole sauce, which is simmered slowly by local restaurant chefs. At the end of the weekend-long event, a panel of chef judges awards top honors to the chefs.
Open House Chicago
Design geeks, take note: for one weekend in mid-October the Chicago Architecture Center coordinates free tours of more than 200 architectural gems around the city, many of them normally off-limits to the public.
Chicago Marathon
More than 45,000 runners compete on the 26-mile course through the city’s heart, cheered on by a million spectators. Held on a Sunday in October (when the weather can be pleasant or freezing), it’s considered one of the world’s top five marathons.
Northalsted Market Days
Boystown lets loose during a mid-August weekend. Revelers gay and straight alike prowl the incense-wafting vendors along Halsted St. Drag queens in feather boas, Twister games played in the street and disco divas on the main stage are a sure bet.
Pride Parade
On the last Sunday in June, colorful floats and risqué revelers pack Halsted St in Boystown. It’s the LGBT community’s main event, and more than 800,000 people come to the party.
Jazz Festival
Top names on the national jazz scene play for free over Labor Day weekend. Performances are held in Millennium Park and the Chicago Cultural Center.
St Patrick’s Day Parade
The local plumbers union dyes the Chicago River shamrock-green; a big parade follows downtown in Grant Park. Held the Saturday before March 17.
Chicago Blues Festival
The biggest free blues fest in the world, with three days of the music that made Chicago famous. Held in Millennium Park.
Pitchfork Music Festival
Taste-making alternative and emerging bands strum for three days in Union Park in mid-July.
Lollapalooza
Up to 170 bands spill off eight stages at Grant Park’s four-day mega-gig.
West Fest
The Empty Bottle lines up ubercool indie bands and DJs for this three-day East Village street fair, which also features food and crafts from neighborhood businesses. It’s usually held the weekend before Pitchfork and is considered the warm up for the tastemaking music fest. The party takes place on Chicago Ave between Damen Ave and Wood St.
Midsommarfest
For over 50 years Andersonville has been celebrating summer with a Swedish twist with this weekend-long neighborhood party along Clark St. Over three nights and two days, live bands and DJs play on five different stages, while street stalls from local restaurants and shops offer up their food and wares. There are Swedish cultural activities and kid-centric programs, too.
Chiditarod
This crazy-costume, Burning Man–esque version of the Iditarod (the famed Alaskan sled-dog race) swaps humans for huskies and shopping carts for sleds. Teams haul canned food for local pantries along a route that starts in front of 235 N Ashland Ave and goes through Wicker Park and Ukrainian Village. Held on the first Saturday in March.
World Music Festival
Musicians and bands from around the world tote their bouzoukis, ouds and other exotic instruments to Chicago for two weeks’ worth of performances in mid-September. Shows take place at venues throughout town, with the Chicago Cultural Center anchoring it.
Chicago Humanities Festival
Put on your thinking cap: for two weeks in late October and early November, a citywide series of chin-stroking talks, panels, readings, performances, exhibits and screenings take place, all focusing on a single academic topic (it was ‘graphic’ in 2018). Ticket prices range from free to $40.
Magnificent Mile Lights Festival
The Saturday before Thanksgiving, Mickey Mouse and a posse of family friendly musicians kick off the holiday season with a free parade that runs along the Magnificent Mile (aka N Michigan Ave). It culminates when they turn on the Mag Mile’s one million lights, which twinkle on into January.
Chicago International Film Festival
This is the city’s main film event. It typically shows a few big-name flicks among myriad not-so-big-name flicks, and brings some big-name Hollywood stars to town to add a glamorous sheen to the proceedings. It unspools over two weeks, starting in mid-October, at varying venues.
Bud Billiken Parade
Held on the second Saturday of August, this huge parade (the USA’s largest African American one) features drill teams, dancers and floats. It runs along Martin Luther King Jr Dr, from 39th St to 55th St, and wraps up with a picnic in Washington Park afterwards.
Taste of Randolph
No wonder this summer fest is a foodie favorite: it unfurls along the main drag of the West Loop, stomping ground of many of the city’s hottest chefs. Expect inventive takes on street fare, plus two stages of indie- and rock-centric live entertainment.
Square Roots
Square Roots is a three-day neighborhood bash in mid-July with suds from local breweries and music stages curated by the Old Town School. It takes place on Lincoln Ave between Montrose and Wilson Aves.
EXPO Chicago
Top galleries from around the globe show off their contemporary and modern art in Navy Pier’s Festival Hall during a long weekend in mid-September. Local galleries get in on the action by offering special tours and programs concurrently.
Printers Row Lit Fest
This popular free event, sponsored by the Chicago Tribune, features thousands of rare and not-so-rare books for sale, plus author readings. The browsable booths line the 500 to 700 blocks of S Dearborn St in early June.
International Mr Leather
The International Mr Leather contest brings out lots of men in, well, leather for a long weekend in late May. Workshops and parties take place around town, with the main event happening at a downtown hotel or theater.
Bike the Drive
The last Sunday in May cars are banned from Lake Shore Dr, and 20,000 cyclists take to the road. Riding 30 miles along the lakefront as the sun bursts out is a thrill. Pancakes and live music follow in Grant Park.
German-American Oktoberfest
Break out the lederhosen and grab a seat in the beer tent at this three-day party in mid-September. The highlight is the big parade – the same one in which Ferris Bueller sang ‘Danke Schoen’ in the famed film.
Chicago Air & Water Show
The third weekend in August, windows rattle as the latest military planes buzz the lakefront from Fullerton Ave south to Oak St. North Ave Beach is the epicenter. Two million people attend the free event.
African Festival of the Arts
Soulful music and global eats bring crowds to Washington Park for this annual event, usually held over the Labor Day weekend in September.
Mayfest
The beer sloshes in steins and everyone dances around the maypole at Mayfest, held over four days in early June to celebrate the community’s German heritage.
Riot Fest
Big-name punk and rock bands scream in Douglas Park near Pilsen for three days in mid-September.
