There are so many great things to do this summer in Chicago. August brings a full schedule of summer block parties, major festivals (like the iconic Lollapalooza and the Chicago House Festival), concerts, sporting events, art exhibits, cultural celebrations, outdoor adventures — all culminating in a jam-packed Labor Day weekend. Check out these top picks for things to do in Chicago this month and beyond.
Check out these top picks for things to do in Chicago throughout August 2025.
Top events in Chicago this August
Lollapalooza (July 31 – Aug. 3): Four days of music, food, and fun take over Grant Park during this iconic summer festival, featuring headline acts like Olivia Rodrigo, Tyler, the Creator, Rüfüs du Sol, and more.
Northalsted Market Days (Aug. 8 – 10): This joyous celebration of LGBTQ+ culture and identity includes five stages of live music and 200+ vendors throughout the weekend in the historic Boystown neighborhood.
Artist’s Garden Flower Show at the Garfield Park Conservatory (through August): This exhibit will showcase Alfredo Ramos Martinez and his vivid celebrations of Mexican culture and beauty through the medium of flowers.
Argyle Night Market in Uptown (through August): Every Thursday evening, this annual night market showcases local restaurants, artisans, and more in the popular Asia on Argyle district.
Chicago Brewing District Dancing in the Streets (Aug. 8 – 10): The West Town neighborhood hosts this live music and beer festival to showcase its vibrant corridor of local breweries.
Bud Billiken Parade (Aug. 9): This year is the 96th annual edition of the world’s largest and oldest African American parade, featuring a procession of bands and floats marching down King Drive on the South Side.
Printers Row Art Fest (Aug. 9 – 10): The South Loop neighborhood holds this annual festival showcasing art, jewelry, sculptures, and more from a variety of local up-and-coming artists.
Maxwell Street Market (Aug. 10): A Chicago tradition dating back over a century, this historic open-air market is the place to score vintage finds, handmade crafts, and plenty of street food and drinks.
Glenwood Avenue Arts District Festival (Aug. 15 – 17): The Rogers Park neighborhood holds its annual summer festival showcasing over 100 artist booths, live music, art demonstrations, local restaurants, and much more.
Chicago Air and Water Show (Aug. 16 – 17): Watch daredevil jets roar overhead during the Chicago Air and Water Show, the oldest free admission event of its kind in the nation.
Chicago International Boat Show (Aug. 21 – 24): Set sail for the marina at Navy Pier, where the Chicago Boat Show docks with a showcase of luxury yachts, fishing boats, water toys, and family-friendly activities perfect for boat lovers of all ages.
Bucktown Arts Festival (Aug. 23 – 24): Local artists come together in the Bucktown neighborhood for the annual arts festival, featuring 100+ local artists showcasing their work.
Chicago House Music Festival and Conference (Aug. 23 – 24): Celebrate this Chicago-born genre with a day of live music from top DJs and dancing in Millennium Park.
Chicago Jazz Festival (Aug. 28 – 31): The free Chicago Jazz Festival wraps up summer in Chicago with a massive Labor Day Weekend festival in downtown Millennium Park.
Taste of Polonia (Aug. 29 – Sept. 1): This annual four-day festival brings Polish culture to the Jefferson Park neighborhood, including authentic food and drink, live music and dance performances, and much more.
AVP League Championship (Aug. 30 – 31): The best beach volleyball athletes in the world battle it out on Oak Street Beach at this iconic summer sports event.
More events in Chicago this August
Jeff Fest (Aug. 1 – 2): This year is the 24th annual edition of Jefferson’s Park’s laid-back neighborhood festival, featuring live music, local eats, and a craft beer garden.
Black Women’s Expo (Aug. 1 – 3): McCormick Place will host the annual Black Women’s Expo, a community celebration focused on engaging, connecting, and uplifting Black women throughout Chicago and beyond.
Millennium Park Summer Film Series (Aug. 5, 12, 19): Grab a spot on the Great Lawn and enjoy free movie screenings in the heart of downtown Chicago all summer long. This month, catch Wicked, Pride and Prejudice, and more.
Chicago Duck Derby (Aug. 7): Head to the Chicago River to watch hundreds of thousands of rubber ducks splash and race, all benefitting the Special Olympics.
Jazzin’ at the Shedd (through August): On Wednesday evenings, explore the Shedd Aquarium after hours while enjoying live music and evening fireworks.
Jazz in the Court (Aug. 8): Catch live jazz performances at alfresco Harper Court in Hyde Park. Local restaurants will be selling cocktails to enjoy with the show.
100 Free Acts of Theater (through August): The Goodman, one of Chicago’s acclaimed theatres, will celebrate its centennial season with free performances and events across the city.
Chicago Greeter Neighborhoods Pop-ups (through August): Dive into a new neighborhood during these free pop-up tours, covering Little Italy, Chinatown, Humboldt Park, and more.
2000s Night at Lincoln Park Zoo (Aug. 9): Relive your glory days at this adults-only night at Lincoln Park Zoo. The after-hours event will feature plenty of throwback tunes, dancing, food, drink, and access to the zoo’s exhibitions.
Taste of Chicago at Albany Park (Aug. 9): The Taste of Chicago visits the Albany Park neighborhood in Chicago, highlighting an array of Chicago food vendors and food trucks, alongside live music, dance, and more.
LatiNxt (Aug. 9 – 10): Hosted at Navy Pier, LatiNxt is a celebration of Latin culture and music that showcases a variety of local artists with a free lakefront music festival.
XL Fest (Aug. 14 – 23): XL Fest is an annual film fest and summit celebrating Black storytellers and industry professionals with panels, film screenings, actor workshops, film pitch competitions, and much more.
Bronzeville Arts District Trolley Tour (Aug. 16): Hop on a free trolley that traverses Bronzeville’s vibrant gallery scene, including the Bronzeville Artist Losts and Gallery Guichard.
Great American Lobster Fest (Aug. 16 – 17): Attendees at this Navy Pier festival can enjoy a variety of lobster-centric dishes, made with fresh Maine lobster flown in daily from the East Coast.
Andersonville Vintage Market (Aug. 17): The bustling Andersonville neighborhood hosts a variety of vendors showcasing their best vintage clothing, home goods, and homemade treasures.
Roscoe Village Porchfest (Aug. 17): Walk the charming blocks of Roscoe Village as residents’ front porches transform into stages for local musicians during this grassroots neighborhood music festival.
Lakeview Taco Fest (Aug. 22 – 24): Dig into inventive and classic tacos from dozens of Chicago vendors at this popular street fest. There will also be beer pairings and live lucha libre action.
Sangria Festival (Aug. 23 – 24): Head to Humboldt Park for a weekend of sipping and sampling all kinds of sangria, plus pop-up food stations, music, and more.
Noche Caribeña (Aug. 23): Spice up your summer with Caribbean rhythms, dancing, and cuisine at this festive night at Navy Pier that highlights Afro-Caribbean culture through music, food, and community.
Chicago Triathlon (Aug. 23 – 24): Cheer on elite athletes over two days as they swim, bike, and run along Chicago’s scenic lakefront.
EEEEEatscon (Aug. 23 – 24): This food festival at The Salt Shed brings together popular restaurants from Chicago and beyond, along with dynamic panel talks, musical performances, and a promise that you won’t leave hungry.
Thirsty Ears Festival (Aug. 23 – 24): This year is the 10th annual Thirsty Ears Festival, which brings classical music to Ravenswood for two days of performances, food trucks, family-friendly activities, and more.
Grant Park Music Fest (through August): This annual festival, held throughout the summer, is the nation’s only free, summer-long outdoor classical music series.
Fireworks at Navy Pier (through August): Catch this spectacular waterfront display on Wednesdays and Saturdays this month — don’t miss out, these are the last shows of the season!
African Festival of the Arts (Aug. 30 – Sept. 1): This immersive event recreates an African village in Washington Park, with live music, yoga, dancing, vendors, and culinary delights.
SummerDance in Chicago (through August): Dance your way through summer at these free outdoor dance lessons, featuring live music and professional instructors.
Movies at Gallagher Way (through August): Gallagher Way at Wrigley Field is offering free summer movie nights, complete with food and drink options and plenty of outdoor family fun.
Green City Market (through August): The buzzing Green City Market is held Saturday and Wednesday in Lincoln Park, bringing together dozens of vendors, from local farms to restaurants, bakeries, and more.
North Coast Music Festival (Aug. 29 – 31): The annual EDM festival returns to Chicago for Labor Day weekend, taking over SeatGeek Stadium in Bridgeview.
