JULY
July 8-11: Windy City Smokeout: It’s like a weekend-long tailgate at this popular country music festival, known for drawing in the industry’s top names.
July 7-11: Taste of Chicago To Go: Known as the biggest free-admission food fest in the country, Taste of Chicago will offer cuisine from restaurants across the city for carry-out and delivery.
July 7-10: Grant Park Music Festival: This 80-year tradition brings free classical music to Millennium Park all summer long.
House City: This new, nine-part series of free events will showcase the Chicago-born genre of house music through pop-up performances in various neighborhoods.
July 31 & August 1: Chinatown Summer Fair: Celebrate the start of summer at this annual fest with cultural demonstrations, traditional dances, and food from Chinatown restaurants.
July 23-25: Wicker Park Fest: This weekend fest celebrates the eclectic neighborhood it calls home with over 50 bands on four stages, local food, a kids’ area, and more.
Tuesdays on the Terrace: The Museum of Contemporary Art offers free live music each week in highlighting artists from Chicago’s internationally renowned jazz community.
Chicago Auto Show: Don’t miss this special summertime edition of the largest auto show in North America.
Chicago Latin Jazz Festival: The scenic Humboldt Park will host this drive-in concert series featuring a line-up of the hottest Latin jazz ensembles.
Millennium Art Festival: This juried art showcase also brings live music and food to Michigan Avenue in Chicago’s Loop.
Jazzin’ On the Steps: The South Side Jazz Coalition kicks off it’s summer series with a return to free jazz on the steps of St. Columbanus Catholic Church.
Music Box Garden Movies: Catch an outdoor film in the newly expanded garden space every night of the week at this beloved Lakeview theatre.
Summer workouts in Millennium Park: Throw on your workout gear and head to the Great Lawn, where you can join free yoga, Pilates, Zumba, and tai chi classes.
Southport Art & Music Fest: Southport Corridor comes to life with a fine art show, featuring jewelry, sculpture, photography, and more.
Bucktown Neighborhood & Garden Walk: Stroll through urban gardens while enjoying live music during this unique event showcasing the Bucktown neighborhood.
Fiesta Del Sol: A multi-day Mexican festival in the Pilsen neighborhood, this annual event is a family favorite.
Jeff Fest: Also known as the Jefferson Park Arts & Music Festival, this neighborhood park takes over idyllic Jefferson Memorial Park.
Lollapalooza: One of the largest and most iconic music festivals in the world, Lollapalooza brings top artists and local bands to lakefront Grant Park.
AUGUST
Lollapalooza: One of the largest and most iconic music festivals in the world, Lollapalooza brings top artists and local bands to lakefront Grant Park.
Northalsted Market Days: An iconic Pride event, Market Days boasts all-day lineups of live music on multiple stages, unique vendors, and DJs and dancing in a historic neighborhood.
Millennium Park Music Series: Grab a spot on the grass and enjoy free weekly concerts by local and national artists.
Chicago in Tune: This new music festival will feature free and ticketed events at venues around the city and iconic Millennium Park.
House City: This new, nine-part series of free events will showcase the Chicago-born genre of house music through pop-up performances in various neighborhoods.
Taste of Greektown: Get a taste of Chicago’s vibrant Greektown with lively bands, dance troupes, and tons of traditional food.
Jeff Fest: Also known as the Jefferson Park Arts & Music Festival, this neighborhood park takes over idyllic Jefferson Memorial Park.
Wells Street Art Festival: This juried art fest and sale draws artists from all over the world to the charming Old Town neighborhood.
Ruido Fest: Billed as Chicago’s only Latin alternative music festival, Ruido Fest offers a weekend of music in Union Park.
Summer Smash Festival: This outdoor multi-stage music festival is returning to Douglass Park with a new three-day format and some of the biggest names in hip hop.
Wine and Art Walk at Morton Arboretum: Just outside Chicago, this sprawling natural area hosts an art fair and wine tasting event on their lovely grounds.
Summer workouts in Millennium Park: Throw on your workout gear and head to the Great Lawn, where you can join free yoga, Pilates, Zumba, and tai chi classes.
Chicago Summerdance: Learn to salsa, waltz, swing, and more during these free open-air dance lessons.
Grant Park Music Festival: This 80-year tradition brings free classical music to Millennium Park all summer long.
Jazzin’ On the Steps: The South Side Jazz Coalition kicks off it’s summer series with a return to free jazz on the steps of St. Columbanus Catholic Church.
Tuesdays on the Terrace: The Museum of Contemporary Art offers free live music each week in highlighting artists from Chicago’s internationally renowned jazz community.
Sangria Festival: Sip sangria while enjoying Latin American food and music at this Humboldt Park festival.
Edison Park Fest This neighborhood tradition supports local businesses and raises funds for the community.
Glenwood Avenue Arts Fest: This arts-centric fest has taken over the streets of Rogers Park for the past 20 years, with artists, craftworkers, live music, and more.
Chicago Triathlon: Athletes from around the world come to compete in this sporting event, which includes a triathlon, super sprint, and kids’ event.
SEPTEMBER
Printers Row Lit Fest: The largest free outdoor literary showcase in the Midwest features speakers and exhibitors across genres.
Chicago in Tune: This new music festival will feature free and ticketed events at venues around the city and iconic Millennium Park.
Pitchfork Music Festival: This multi-genre music festival is known for it’s cutting-edge line-up and laidback vibe.
African/Caribbean International Festival Of Life: Reggae music is at the heart of this Washington Park festival, along with the lifestyle and culture of various African and Caribbean nations.
Roscoe Village Burger Fest: Find the best burger in the city at this local favorite, all while enjoying live music and cold drinks.
Riot Fest & Carnival: One of Chicago’s biggest music fests, Riot Fest brings rock, punk, and a full carnival to Douglass Park.
Hyde Park Jazz Festival: This free festival celebrates the rich tradition of jazz on Chicago’s south side, featuring a diverse group of musicians each year.
House City: This new, nine-part series of free events will showcase the Chicago-born genre of house music through pop-up performances in various neighborhoods.
Chicago Summerdance: Learn to salsa, waltz, swing, and more during these free open-air dance lessons.
¡Súbelo!: Head to the vibrant Pilsen neighborhood for this celebration of Latinx music and culture.
Hyde Park Summer Fest: Fest-goers can enjoy craft beer, food, and music on the historic Midway Plaisance.
ARC Music Festival: This new fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.
Puerto Rican Festival: In Humboldt Park, this vibrant street fest showcases Puerto Rican culture and history.
Millennium Park Music Series: Grab a spot on the grass and enjoy free weekly concerts by local and national artists.
Chicago Gourmet: This high-end food festival features tastings, demos, and intimate dinners with the country’s best chefs.
Wright Plus Architectural Housewalk: For one day only, tour the interiors of private residences and landmark buildings designed by Frank Lloyd Wright and his contemporaries.
North Coast Music Festival: This annual Labor Day weekend music festival includes electronic music, hip hop and rock acts, plus art installations and food vendors.
Sam Adams’ Lakeview Taco Fest: Enjoy the last few days of summer with tacos, margaritas, entertainment, and more at Southport Corridor.
Chicago International Latino Theater Festival: The city’s Latino theater community is on display during this month-long festival.
Global Peace Picnic: The scenic boathouse in Humboldt Park will be the backdrop for this afternoon of family-friendly activities and international music performances.
OCTOBER
Pride Fest & Parade: This annual LGBTQ+ celebration (typically held in June) draws people from all over the world to the streets of Northalsted for an over-the-top festival and parade.
Chicago Marathon: Runners from all over the world come to Chicago to run a scenic 26.2 miles through the city’s neighborhoods.
Chicago Beer Festival: Sip seasonal brews from more than 60 local breweries while wandering through the iconic Field Museum.
Chicago International Latino Theater Festival: Discover emerging voices in the local Latino theater community during this multi-faceted fest.
Chicago International Film Festival: After more than five decades, North America’s longest-running competitive film festival gets bigger and better each year.
Open House Chicago: This one-of-a-kind (free!) architecture festival takes you inside many of Chicago’s coolest buildings, skyscrapers, and more.
Historic Pullman House Tour: Tour the interiors of private homes, from workers cottages to landmark mansions, during this unique event in historic Pullman.
Inherit Chicago: This citywide, intercultural festival highlights the rick diversity of Chicago’s neighborhoods.
Lincoln Square Apple Fest: Celebrate the fall harvest with apple pie, apple cider, artisan goods, and more.
Lincoln Park Wine Festival: Sip wines while strolling through an open-air market of sommeliers, food tastings, and live music.
Columbus Day Parade: A celebration of Chicago’s Italian community, the festivities include a mass and wreath laying ceremony.
Latino Music Festival: With a mission to present Latino music in all its breadth and depth, this annual music fest features a wide array of performers.
Randolph Street Market Festival: This sprawling, lively antique market sets up shop in the trendy West Loop several times a year.
Arts in the Dark: Celebrate the artistic side of Halloween at this twilight parade, featuring puppets, performers, whimsical floats, and more.
Northalsted Halloween Parade: In the Northalsted neighborhood, this spooky spectacle includes a costume contest, trick or treat for dogs, dance performances, and more.
NOVEMBER
Magnificent Mile Lights Festival : A beloved tradition, this spectacular holiday event includes a parade and the official lighting of the tree
Christkindlmarket Chicago: Grab a mug of hot wine and stroll through this magical holiday bazaar, styled after traditional German Christmas markets.
Randolph Street Holiday Market: This sprawling, lively antique market sets up shop in the trendy West Loop several times a year.
Intersect Chicago: Held at Navy Pier, this long-running art fair focuses on three-dimensional artworks along with talks and events.
Festival of Barrel Aged Beers: Taste the rarest, most exclusive wood and barrel-aged beers from more than 100 brewers at this cult-favorite competition.
Caroling at Cloud Gate: Join in on this holiday sing-a-long held in front of “The Bean” in Millennium Park.
Christmas Tree Lighting Ceremony: A holiday favorite, the annual lighting of the towering tree in Millennium Park is always spectacular.
Zoolights at Lincoln Park Zoo: This over-the-top light display, which includes more than one million twinkling bulbs, is a beloved local tradition.
Lightscape at Chicago Botanic Garden: Be awed by this magical outdoor light show that takes over these sprawling Glencoe gardens.
Illumination: Tree Lights at The Morton Arboretum: Each winter, the trees at this Lisle nature attraction come to life with festive lights and music.
Thanksgiving Parade: Head to historic State Street to catch giant floats, dancers, horses, special guests, and more.
Ice skating in Millennium Park: Grab your skates and check out the two scenic (and free!) ice rinks that pop up in iconic Millennium Park each winter.
DECEMBER
One of a Kind Show and Sale: Find unique items, housewares, jewelry, gifts, and more handmade by local creators.
Winter Wonderfest at Navy Pier: This annual holiday celebration includes an indoor wonderland of rides and games.
Randolph Street Holiday Market: This sprawling, lively antique market sets up shop in the trendy West Loop several times a year.
Historic Pullman Candlelight House Walk: This magical neighborhood event includes tours of stunning historic homes decked out for the holidays.
Christkindlmarket Chicago: Grab a mug of hot wine and strol through this magical holiday bazaar, styled after traditional German Christmas markets.
Lightscape at Chicago Botanic Garden: Be awed by this magical outdoor light show that takes over these sprawling Glencoe gardens.
Zoolights at Lincoln Park Zoo: This over-the-top light display, which includes more than one million twinkling bulbs, is a beloved local tradition.
Illumination: Tree Lights at The Morton Arboretum: Each winter, the trees at this Lisle nature attraction come to life with festive lights and music.
Ice skating in Millennium Park: Grab your skates and check out the two scenic (and free!) ice rinks that pop up in iconic Millennium Park each winter.
New Year’s Eve Fireworks at Navy Pier: Ring in the New Year with a breathtaking fireworks display over Lake Michigan.
Please note that dates are subject to change. Visit individual event websites for details and the latest updates.