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Hey friends! Summer in Chicago is busy as ever, and I know that it can get overwhelming trying to keep up with all of the incredible local events. Here’s a handy guide to all the hot tickets of this month, in case you need some inspiration!

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Music

• Lollapalooza | 8/1-8/4
  • Annual four-day music festival located in Grant Park, showcasing more than 150 artists and band across eight stages. Headliners this year include Megan Thee Stallion, SZA, The Killers and Blink-182!
• Bronzeville Neighborhood Jazz Festival | 8/5
  • From 10am-9pm, head to King Drive in Bronzeville for hours of live jazz and blues performances – entry is free.
• Chicago Brewing District’s ‘Dancing in the Streets’ | 8/2-8/4
  • This weekend event showcases West Town’s beer scene while providing days of live music, local food, and dancing – and also honoring Jerry Garcia of the Grateful Dead! Located on Hubbard St. with event times varying by day.
• North Coast Music Festival | 8/30-9/1
  • EDM lovers will find themselves at home during this annual music festival, which takes place in Union Park over Labor Day Weekend.
• Chicago Jazz Festival | 8/29-9/1
  • Honor the Windy City’s rich jazz history at Millennium Park with performances from both up-and-coming artists and major players alike. Admission is free. 

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Windy City Fun

• Chicago Air and Water Show | 8/10-8/11
  • North Avenue Beach is the best spot to view the oldest, largest free air and water show in the country. 
• Chicago Triathlon | 8/24-8/25
  • The biggest short-course triathlon in the country, consisting of a swim in the lake, biking through the streets of Chicago, and a run that ends in Grant Park. Register online or attend to support someone you know!
• Chicago Ducky Derby | 8/7
  • This unique event raises money for Special Olympics Illinois – thousands of rubber ducks will be released into the river, with ‘adoptees’ having a chance to win prizes if their duck finishes first. Participate by adopting a duck, or attend to watch the river turn rubber yellow!

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Neighborhood Events

• Bud Billiken Parade | 8/10
  • 2024 marks the 95th anniversary of this celebration, which is the largest African-American parade in the United States (and the second-largest overall parade, second only to the Rose Bowl). After watching it all from Martin Luther King Jr. Drive, head to Washington Park for additional festivities. 
• Chalk Howard Street | 8/24
  • Whether you’re participating in the creation or want to see professional chalk art take over the streets, Chalk Howard Street in Rogers Park is sure to be a colorful time. Taking place between 11 am and 8 pm.
• Retro on Roscoe | 8/9-8/11
  • If you’re feeling nostalgic, this Roscoe Village festival will send you on a blast to the past with a weekend full of live throwbacks! Shop among local merchant stands, enjoy the oldies, and stop by the Antique Car Show to top it all off.  
• Northalsted Market Days | 8/10-8/11
  • The vibrant neighborhood of Northalsted is rich in LGBTQ+ culture, shown off during this award-winning festival (2023 Best of GayCities Winner for Travel Worthy Festival). This year’s street fest will host performers across five stages. 
• Edison Park Fest | 8/2-8/4
  • Bands! Bike parades! Inflatables! Bingo! This one offers something for everyone, and proceeds go right back to the community. $10 donation requested.

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Art Fests and Markets

• Glenwood Avenue Arts Fest | 8/16-8/18
  • Activities include the Cobblestone Jam on Friday night and art markets on Saturday and Sunday, all taking place in Rogers Park’s arts and entertainment district. Some art installations even request audience participation! 
• Printer’s Row Art Fest | 8/10-8/11
  • About 100 artists/artisans will be displaying their works along Dearborn St. for this event. Check out the Kids Art Zone for face-painting or visit the live art demo area to interact with artists.
• West Loop Arts Fest | 8/30-9/1
  • Fulton Market’s festival is on the larger side – six blocks of art and amassing an average of 25,000 visitors annually. Free to the public!
• Andersonville Vintage Markets | 8/18
  • The Andersonville Vintage Markets take place one weekend/month during the summer, with variations in performances and vendors for each iteration.  

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Food

• Great American Lobster Fest | 8/10-8/11
  • Hungry after watching the Air & Water Show? Craving seafood? Navy Pier is the place to be! If you’re not a crustacean fan, don’t worry; there are non-seafood options available too – and desserts! 
• Sangria Festival | 8/17-8/18
  • Humboldt Park is serving up delicious food and drink, both day and night. Attendants can compete in a picnic table competition, sip multiple flavors of delicious sangria and join in the dancing. Performances will include a variety of music and dancers showcasing styles such as flamenco and samba!
• West Chicago Food Festival | 8/24
  • Bring your friends and your folding chairs to downtown West Chicago to enjoy an afternoon of cuisine from more than twenty local vendors, along with other entertainment for children and adults alike.  

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Whether you’re new to the city, local, or hosting visitors, August is full of adventures sure to excite everyone. Try something new this month and experience the joys of Chicago’s thriving communities!