Things to Do in Chicago in August

By the time August rolls around, Chicagoans know their days of summer are numbered, and they act like it. The neighborhood street fest calendar thins out a little, but August has two of the biggest weekends of the year, a parade that's been running since 1929 and the last few weeks of beach season. Here are the highlights.

Dates move every year, so this page tells you roughly when things happen. For exact dates, check the city's festival dates page or each event's own site. If you're still working out when to come and what to pack, start with Chicago in August.

Lollapalooza (late July or early August)

Lollapalooza takes over Grant Park for four days, not the three we used to list, with more than 170 artists on eight stages. It's ticketed, and the fences go up days before, so if you're not going, plan your Buckingham Fountain visit for another week. The Red Line stops at Monroe, Jackson and Harrison, two blocks west of the park.

Northalsted Market Days (early August)

Market Days fills half a mile of Halsted Street between Belmont and Addison in Lakeview, and it's now three days long, starting Friday evening. Expect four music stages, more than 250 vendors, drag shows, dancing and a very big crowd of gay, lesbian and straight people all out to let loose in the street. The suggested donation at the gate is $20. Take the Red Line to Addison or the Red, Brown or Purple Line to Belmont. Our gay Chicago page has more on the neighborhood.

Bud Billiken Parade (second Saturday in August)

The Bud Billiken Parade is the city's back-to-school send-off, and it has marched every summer since 1929. Robert S. Abbott, publisher of the Chicago Defender, dreamed up Bud Billiken as a character for the paper's youth column. Today it's the largest African American parade in the country, with bands and floats heading south on Dr. Martin Luther King Jr. Drive from 35th Street through Bronzeville, and a picnic in Washington Park at the end. If you've only seen the city from the Loop, this is a great day to see the South Side.

Chicago Air and Water Show (mid-August)

The Air and Water Show has run since 1959, and the city bills it as the largest free show of its kind in the US. It's a Saturday and Sunday from late morning into mid-afternoon, and you can watch from anywhere on the lakefront between Fullerton Avenue and Oak Street, with North Avenue Beach at the center. The pilots also fly a rehearsal on the Friday, when the lakefront is a lot less packed. The 72 North bus runs to North Avenue Beach, and our tips for attending the Air and Water Show has more.

Taste of Greektown and House Music Fest (late August)

Taste of Greektown closes out the month with Greek food from the neighborhood's restaurants, live Greek music and dancing on Halsted Street between Adams and Van Buren in the West Loop. Admission is free.

Late August has also brought the city's Chicago House Music Festival and Conference, which in 2026 ran four days of free DJ sets, dance and talks at the Chicago Cultural Center, Grant Park, the Riverwalk and around town. House music was born here, and this is the city's party for it.

Free music in the parks

Summer's free outdoor series wind down during August, so catch them while you can. The Grant Park Music Festival plays free classical concerts at the Pritzker Pavilion in Millennium Park, and Chicago SummerDance runs free dance lessons followed by live music in July and August, including at the Spirit of Music Garden in Grant Park. Bring a blanket and a picnic. See free summer events in Millennium Park and Grant Park.

Outdoor things to do

August is the last full month for swimming. The beaches have lifeguards until Labor Day, and North Avenue and Oak Street are the busiest. The farmers markets are at their best now, with sweet corn, tomatoes and Michigan peaches. Catch the Cubs at Wrigley Field, take an architecture cruise on the river (see sightseeing tours), or find a patio from our list of outdoor dining spots. There's usually a neighborhood street fest somewhere on any given weekend.

When it's too hot

A 90-degree afternoon is a good excuse to go inside. The museums are cold and there are plenty of them. The National Museum of Mexican Art in Pilsen is always free, and the Museum of Contemporary Art is free for Illinois residents on Tuesday evenings. Our free museum days page tracks the rest. For more ideas, see ways to beat the heat, breweries and brewpubs and things to do on rainy days.

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Photo by akeg