Those sweet summer days we’ve waited for all year long are flying by faster than a Thunderbird jet, which you can spot at the Chicago Air & Water Show later this month. In the spirit of squeezing all we can from Chicago’s most spectacular season, we’ve compiled the best things to do in Chicago and the suburbs this August 2025.
Tag us in your summer adventures on Instagram @makeitbetter_foundation — we’d love to see where the month takes you.
All Month
July 18-August 10: Billie Jean at Chicago Shakespeare Theater
Chicago Shakespeare Theater, a Make it Better Foundation grant content partner, presents the world premiere of an electrifying new play about Billie Jean King. Following her path to becoming a sports icon, from her record-breaking victories to her relentless fight for equal rights, Billie Jean brings us closer than ever to a woman whose battle for equality has inspired generations.
Gustave Caillebotte: Painting His World
Impressionist artist Gustave Caillebotte (1848–1894) — known and beloved by many Art Institute visitors for his monumental painting Paris Street; Rainy Day — takes center stage in this major exhibition exploring the very personal interests and relationships that shaped his world. Catch it through October 5, details at the Art Institute online.
BOOK UP! In partnership with Chicago Parks District
A traveling librarian rolls into town with their magical book cart, ready to spark big imaginations everywhere through juggling, tumbling, clowning and aerial acrobatics! This wonderous outdoor circus spectacle invites children ages 0-5 (and their grown-ups!) to move, play, and discover the magic of reading. All performances are free.
Jazzin’ at the Shedd
On Wednesdays through August 27, live jazz fills Shedd Aquarium. Join them for the 30th anniversary of the popular midweek Jazzin’ at the Shedd series with unforgettable evenings of music, mingling and marine life. Stroll through the aquarium to the soundtrack of jazz styles from around the world as you encounter animals from every corner of the map.
Free Summer Screenings
Summer Screenings return with “Summer of Love,” featuring 21 free films from 21 countries about the ways love manifests in our lives. Held at the Chicago Cultural Center on Mondays and the Chicago History Museum on Wednesdays, each film will spotlight a different country’s national cinema all summer long. Catch this series through August 20.
Contemporary Drawings from the Stenn Family Collection
Voraciously curious and contagiously enthusiastic about art, Chicagoan Irving Stenn Jr. has across five decades assembled a spectacular collection of 20th-century art from various movements and across the world.
Chicago SummerDance
Enjoy live music and dancing on an open-air dance floor during the annual Chicago SummerDance festival. This summer-long event series brings people together in the city’s scenic parks for evenings filled with music, dance, community, and celebration. Each event features lessons from a professional dance instructor, featuring more than 30 unique dance styles from around the globe.
Tuesdays on the Terrace
Enjoy free music on the MCA’s Anne and John Kern Terrace Garden with the annual summer concert series — now in its 26th year. Tuesdays on the Terrace continues to offer an expansive lineup of diverse musical acts, with genres like pop, soul, R&B, jazz and more. Plus light fare and refreshments from the bar, while relaxing on the terrace. Find more details online at Tuesdays on the Terrace — now through August 26.
Paddle and Plant
Join Friends of the Chicago River and Shedd Aquarium to paddle, explore and volunteer to improve the health of the Chicago-Calumet river system this summer. Volunteer for one of the Paddle and Plant events to put in aquatic plants along the river’s edge, a unique opportunity to put on waders, head out in canoes, park along the banks of the waterway, and install native plants. These plants improve habitat and water quality, in addition to improving our resiliency to climate change.
Movies at the Parks
The beautiful Chicago Parks system returns with the Movies in the Parks series, a part of the larger Night Out in the Parks initiative. Enjoy family-friendly movies that range from newer releases to kid favorites, all while reclining on the lawn of your local park. Head over to the Chicago Park District online for dates, locations and movie lineups — catch it anytime before August 27.
Pouring Park: A Global Cocktail Journey
From now through the new year, celebrate Park Hyatt’s 45th anniversary with a global cocktail journey—no passport needed. Enjoy iconic drinks from nine destinations, each crafted to reflect its culture. Every 45 days, two new cocktails debut at participating locations, offering a taste of the world, one sip at a time.
July 31-Aug. 3: Lollapalooza
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Live music lovers from near and far know that summertime in Chicago also means Lollapalooza, the epic, 4-day festival that brings thousands to Grant Park — this year through August 3. Headliners this year include Tyler, The Creator, Sabrina Carpenter, and so many more talented acts. Some ticket packages — from single day tickets to 4-day passes — are still available on the Lollapalooza website.
August 1-3: Fiesta del Sol
For over 50 years, Fiesta del Sol has proudly been the “largest Latino festival of its kind in the country.” Held in Pilsen, and known for its stages full of talented artists, Fiesta del Sol is meant for anyone who loves live music, authentic food and the embrace of a community. The Fiesta del Sol website features a recap of last year’s event for anyone curious before they buy their ticket — though we are pretty sure you’re going to enjoy yourself either way! This fest runs until August 3.
August 7: Chicago Ducky Derby
Locals and tourists alike can agree that an adorably yellow addition to the Chicago River is an annual treat for all to see. We’re talking about the Chicago Ducky Derby, of course! Every year, the city dumps thousands of toy duckies into the river — and with the sponsorship of Special Olympics Illinois, proceeds go to their organization. Want to get involved? Besides heading downtown to watch the event, guests can also purchase and donate their own ducks to be set free during the event — helping them get all the closer to their goal of 100,000 ducks. Head over to Chicago Ducky Derby online to be part of the fun!
Pioneer Court, 401 N. Michigan Ave.
August 8-10: Northalsted Days
Celebrating for over 40 years in what is formerly Boystown, the Northalsted Market Days is a weekend filled with live music, drag performances, endless vendors, food and drinks. In Chicago’s most queer-friendly neighborhood, don’t miss the chance to publicly celebrate your Pride outside of June. All ages are welcome to this event. There is a suggested $20 donation fee for entry, more information can be found on the Northalsted Market Days website.
On Halsted, from Addison to Belmont
August 10: 96th Annual Bud Billiken Parade
For 96 incredible years, the Bud Billiken Parade has proudly marched down King Drive as “a commemoration of our past and a celebration of our future.” Since 1929, the parade has served as a space for Black Chicagoans to “openly and emphatically praise the historic roots that plant us into the South Side of Chicago.” The community-focused event will also include music, dance, food and more! Visit the Bud Billiken Parade online for event and route details.
August 10-11: The Great American Lobster Fest
A nice lobster roll and a cool drink on a summer day, doesn’t that sound wonderful? Well it can be your reality this month at The Great American Lobster Fest held at Navy Pier. This two-day, day-long fest devoted to the delicacy that is lobster will have shell-fish fans ecstatic and may even convert new-comers. A meal ticket gets you quite the spread, all of which includes access to live music and purchasable crafts from vendors, as well as fireworks on Saturday. This event is 21+ and perfect for a group outing. Visit The Great American Lobster Fest to save your spot.
800 E. Grand Ave.
August 13: 14th Annual Garlic Fest
Celebrate Highwood’s 13th annual Garlic Fest is back on Wednesday, August 14th from 4:30-9:30 PM in Everts Park (111 North Avenue). Held in conjunction with Highwood’s Evening Gourmet Market, this foodie fest showcases a plethora of garlic dishes, garlic trivia contest, live music and plenty of family-friendly activities.
August 15-17: 47th Annual Mid-America Bonsai Exhibition
Join the Midwest Bonsai Society’s 47th August Exhibition at the Chicago Botanic Garden. Featuring over 150 world-class bonsai trees, vendors, workshops, and family activities!
August 15-17: Glenwood Avenue Arts District
Annually for more than 20 years, over a hundred artists, studios and makers gather for the weekend-long Glenwood Avenue Arts Fest. During the fest, attendees can view and purchase handmade artwork, jam out to free live music and art demonstrations, as well as sample street food and craft beer from local vendors in the historic Rogers Park neighborhood. Sure sounds like a can’t-fail outing to us! Check out the Glenwood Avenue Arts Fest website for more.
Glenwood Ave. and Morse Ave.
August 16-17: Wine and Art Walk at Morton Arboretum
Visit The Morton Arboretum to sip wine and other beverages while you take in gorgeous summertime views of Meadow Lake and browse nature-themed artworks. The Wine and Art Walk is a juried art show featuring photography, woodturning, jewelry, painting, ceramics, fused glass, fiber arts, and more artworks created by artists in the Midwest and beyond. Find details at Wine and Art Walk at Morton Arboretum
August 16-17: Chicago Air and Water Show
Hundreds flock every year to share in the beauty of our city, even if just as a backdrop to the excitement of the annual Air & Water Show. While there, expect air crafts and water-bound vessels to display their majesty to the crowds gathered on the shore. Well-known for being a beloved family outing, the Air & Water Show is a spectacular, free way to spend the weekend outdoors. Event details can be located on the Chicago Air & Water Show page.
Fullerton to Oak Street
August 17: Bloody Mary Fest
Do you like your Bloody Mary spicy or mild? How about piled high with endless garnishes? No matter how you take it, you’ll find something worth sipping on at the Bloody Mary Fest in Highwood. This year’s participants are planning all kinds of twists to the classic tomato cocktail, and a contest for the most-voted, fan-favorite vendor will take place as well. Want to have a say in who takes home the hardware? Head to the Bloody Mary Fest website for more details.
Everts Park, 111 North Ave.
Aug. 20: 3rd Annual Taste of Ravinia Farmers Market
the Taste of Ravinia Farmers Market returns for its third year — offering a full day of food, music, and community spirit in Highland Park. Presented by the Ravinia Farmers Market and the Ravinia Neighbors Association, the day kicks off at Jens Jensen Park (450 Roger Williams Ave.) from 7 a.m. to 1 p.m. with the weekly Ravinia Farmers Market, where more than 20 vendors will offer fresh produce, handmade goods, and ready-to-eat bites. From 4 to 9 p.m., the celebration continues at the Ravinia Festival Grounds (200 Ravinia Park Rd.) with additional vendors and a ticketed concert on the Carousel Stage featuring Henhouse Prowlers with Almond & Olive, The Lucky Pickers, and Noah’s Jam Jam Bourrée.
Looking for a market closer to home? Check out our complete 2025 guide to Chicago and North Shore Farmers Markets to find one near you.
August 22-24: Skokie’s Backlot Bash
A carnival, 5K race, live music, bingo, plenty of refreshing food and drinks — this and more attendees can expect from Skokie’s Backlot Bash. The bash is meant as a celebration of all things uniquely Skokie, and therefore highlights local musicians and community-based vendors. Want to get your groove on alongside your community? Check out Skokie’s Backlot Bash for details.
Downtown Skokie
August 22-24: Taste of Greektown
The popular Taste of Greektown festival returns for its 35th year with the city’s largest celebration of Hellenic cuisine and culture, along Halsted Street from Adams to Van Buren. The neighborhood’s acclaimed Greek restaurants are the stars of the show, including well-loved restaurants young and old. Taste of Greektown will also offer live music and entertainment, Greek dancing, unique shopping and retail, and family activities. For more information, visit GreektownChicago.org.
August 23: Unbound: Shattered Frames, Endless Visions
A groundbreaking premiere, the Chicago Black Dance Legacy Project’s performance spotlights ten of Chicago’s most compelling dance companies across diverse artistic genres — including contemporary, jazz, tap, and much more.
August 23-24: 2025 Chicago Triathlon
Voted the Best Sprint Triathlon in the USA, the Chi Tri is one of the world’s largest and most accessible triathlons. From first-timers to seasoned veterans, kids to grandparents, age-group competitors to paratriathletes, the Chicago Triathlon has an experience for everyone on the shores of Lake Michigan. Find out more about spectating at 2025 Chicago Triathlon.
August 28-31: Chicago Jazz Festival
All throughout Chicago, the city is flowing over with talented musicians. Countless outdoor festivals cater to a plethora of genres, but few do justice to jazz music like the Chicago Jazz Festival held at Millennium Park and the Chicago Cultural Center every summer. This multi-day fest kicks off at the end of this month. If you fancy jazz music and want to feel one with your community, there is no better place than the Chicago Jazz Festival — visit their website for entry details.
August 31: Bike The Drive
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Whether you’re new to biking or a seasoned veteran, biking with your family or with friends — Bike the Drive is an event to remember. With sweeping views of the lake and skyline, you’ll enjoy fresh air and the wind on your face! Ride as little or as much of the 30-mile course as you’d like, and then enjoy a post-ride festival in Grant Park. No bike? No problem! Rentals are available. Get the details at bikethedrive.org.
More from Better:
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- A Silent Crisis Is Undermining Global Food Security — These Scientists Have a Solution
- 14 of the Best Things to Do on Chicago’s North Shore This Summer 2025
Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.
