It’s hard to believe that the beginning of a new month is already here, which means there are many new things to discover in Chicago in August.
Whether you’re a foodie in search of an undiscovered spot, an outdoorsy type craving fresh air, or a creative looking for new experiences, Secret Chicago has got you covered. From new restaurants and food festivals to must-see exhibitions and unique live performances, these ideas will definitely get the ball rolling. Take a look at this comprehensive list of the best things to do in Chicago in August, and start planning your month!
Attend Lollapalooza
Taking place July 31 – August 3, 2025, this year, Lollapalooza is one of Chicago’s beloved music festivals. The major headliners include Olivia Rodrigo, Sabrina Carpenter, Doechii, Gracie Abrams, and more. The annual music festival is one of the best things to do in chicago in August.
Sponsor a duck at the Chicago Ducky Derby
Every summer, tens of thousands of yellow ducks splash into the Chicago River in a lip-biting race for the Chicago Ducky Derby, all to raise money for Special Olympics. One of the best things to do in Chicago in August is to watch the spectacle from the downtown area, where Chicagoans flock and line up on bridges and along the riverwalk.
Many adopt a duck or five in the hope of winning big and supporting the Special Olympics in the process. Each year, the event raises over $300,000 for more than 20,000 athletes and nearly 10,000 young athletes.
Embark on a tranquil journey through thermal baths, steam rooms, and relaxing massages at AIRE Ancient Baths
Make the most of your summer with a guided experience through the soothing services offered in AIRE Ancient Baths. Located in a restored 1902 factory in River West, AIRE is offering a Summer Essential experience that provides access to thermal baths ranging from hot to cold temperatures.
The Summer Essential experience also features a body massage with AIRE’s Signature Orange Garden oil that’s been scientifically proven through Functional Magnetic Resonance Imaging (fMRI) to improve relaxation. Click here to learn more about the Summer Essential ritual and book your visit!
Watch the Chicago Air & Water Show
Of all Chicago’s exciting annual summer events, the beloved Air and Water Show is undoubtedly one of the headline acts. The largest free show of its kind in the entire country is coming back for another full-throttle experience above Lake Michigan, and this year, the U.S. Air Force Thunderbirds will be making their first appearance in Chicago since 2018.
Having once again returned to full-scale shows last year, the 2025 Chicago Air & Water Show is expected to attract over 2 million spectators who will flock to watch the aerial daredevil feats. Spectators can once again line up along North Avenue Beach and the Lakefront, from Fullerton to Oak Street, and enjoy a variety of military and civilian performances absolutely free from 10 am to 2 pm on August 16-17, 2025.
Eat lobster at Navy Pier’s Great American Lobster Fest
With Chicago’s Air & Water Show already providing reason enough to keep the third weekend in August free, another cherished annual event adds even more reason to spend that weekend on the lakefront.
Returning for its eighth year, the Midwest’s largest lobster and seafood festival, Great American Lobster Fest, will take place the same weekend as the air and water show on Saturday, August 16, and Sunday, August 17.
The family-friendly festival on Navy Pier features live music and, more importantly, a vast array of seafood, including lobsters flown in fresh from the cold waters of the East Coast.
Catch a weekly Navy Pier firework show
One of the best things to do in Chicago in August is the weekly Navy Pier fireworks display, which will light up Lake Michigan. The pier’s fireworks displays are completely free and will take place every Saturday at 10:00 p.m. and every Wednesday at 9:00 p.m. through Labor Day weekend.
Onlookers can find a spot anywhere on the pier to take in the dazzling display completely free of charge. According to the Navy Pier website, there will be accompanying soundtracks featuring dramatic and popular music.
Take in the fireworks from the water
Another option, if you want to make it a really special Wednesday or Saturday night, is to watch the fireworks from the waters of Lake Michigan with a Chicago Lakefront Fireworks Cruise. With the mesmerizing Chicago skyline in the backdrop, you’ll be spellbound as fireworks illuminate the night sky.
Alternatively, the Sunday Funday Party Cruise! provides the perfect remedy for the Sunday scaries, and Chicago Booze Cruises offer midweek plans throughout the week, featuring live DJs, unobstructed views of the skyline, and the chance to make memories as the sun sets over Lake Michigan.
Kayak down the Chicago river
Of course, if you’re not kicking back down at the lakefront, there is a good chance you’ll spend some of your summer enjoying the vibrancy of the Chicago Riverwalk. But rather than sit on the side, why not take it in from the river itself?
Thanks to Urban Kayaks, another unforgettable water activity can be enjoyed in the center of Chicago from the comfort of a kayak. Flanked on either side by Chicago’s famous high-rise architecture, you can venture through the city’s heart via skyscraper canyons and under historic bridges.
An evening kayak makes for a truly memorable night navigating the waters while the sun sets and the hustle and bustle of the riverwalk activity takes off around you.
Check out London House’s “Luminescence” experience
London House Chicago, a luxury hotel renowned for its unparalleled views of the Magnificent Mile and the Chicago River, has revived its summer “Luminescence” experience on its iconic 22nd-floor terrace.
The award-winning rooftop hosted its inaugural summer experience last year, featuring a never-before-seen vibrant array of multi-colored, floral-themed LED lights sprawled across walls and hanging over the iconic rooftop.
Guests can now enjoy a “kaleidoscope of colors” and “mesmerizing ambiance” every day of summer!
Read more about London House Chicago’s “Luminescence” experience.
Be captivated by a Candlelight Concert
Chicago’s sublime Candlelight Concert series is providing an array of breathtaking spectacles in the Windy City. Talented musicians will perform at extraordinary venues throughout Chicago, offering guests the chance to marvel at the enchanting combination of flickering candles and melodic sounds.
See the full list of candlelight concerts in Chicago here.
Shop until you drop
There is nothing better than opening the door to your local vintage store, sifting through a plethora of clothing, and finally coming across a beautiful jacket, a patent leather purse, or a set of antique painted plates—all at an affordable price.
Read more about all the vintage stores in Chicago here.
Check out your favorite artist at a concert
We firmly believe that Chicago has one of the greatest music scenes—the Smashing Pumpkins, Styx, Jennifer Hudson, Chance the Rapper, and many other artists were discovered here. Whether you’re into R&B, Rap, Indie Rock, or Pop, there is a stream of festivals and artists coming to perform in Chicago, from intimate dive bars to Wrigley Field.
Enjoy dinner with a show
Whether you like to twirl to country music while devouring barbecue or sip on a refreshing cocktail on center stage as a soul band, there’s no shortage of amazing bars and restaurants with live music in Chicago.
Read more about the restaurants with live music here.
Attend a Concert Under The Stars
Concerts Under the Stars is another terrific outdoor musical experience taking place this summer with concerts such as ABBA Under The Stars at AIRE on August 27. You’ll enjoy a night of ABBA accompanied by stunning views from the rooftop of the AIRE in Chicago.
Attend a Tuesday on the Terrace at MCA
Every Tuesday through summer, the Museum of Contemporary Art hosts Tuesdays on the Terrace—a free musical event series for Illinois residents. It offers Chicagoans a chance to turn a typical underwhelming Tuesday into a jubilant evening at the MCA’s Anne and John Kern Terrace Garden, where they can experience free music that highlights artists from Chicago’s internationally renowned jazz community.
Tuesdays on the Terrace have shows running from 5:30 pm until 8 pm every Tuesday through to the end of summer.
Revel in the Retro on Roscoe street party
Retro on Roscoe Street will be spread out across six blocks of Roscoe Village, featuring amazing local food, antique vendors, family-friendly activities, and, of course, live music across three stages guaranteed to keep the party moving.
Enjoy some of the extraordinary exhibitions taking place in Chicago this year
One of Chicago’s most impressive qualities is its collection of world-class museums and the array of exhibits they offer. This year a whole host of new extraordinary art exhibits are coming to the Windy City.
Art, science, and human connection have a truly transformative power, and now, after the tumultuous and unprecedented years that we’ve just endured, it’s time to remember that.
Read more about some of the most unique exhibitions taking place in Chicago this year.
Browse some of the world’s most famous artworks for free
One of the planet’s oldest and largest art museums, the Art Institute of Chicago is undoubtedly one of the city’s most renowned museums. Since its founding in 1879, it has flourished into one of the most recognized art museums in the world.
The museum is permanently home to over 300,000 works of art, including masterpieces such as Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday on La Grande Jatte, Vincent van Gogh’s The Bedroom, 1889, and Pablo Picasso’s The Old Guitarist.
Get free entry to Adler Planetarium on a Wednesday
Another of Chicago’s famed attractions, The Adler Planetarium, underwent a huge revamp during a two-year Covid-19-induced hiatus and now boasts a brand new telescope in the Doane Observatory, which holds the title of the largest public telescope in the state.
As well as a new observation park, the planetarium has a shiny new roof, giving the 80-year-old dome an iconic new glow. However, the best news is that upon its reopening, the planetarium announced that Illinois residents would be able to enter for free every Wednesday evening from 4-10 p.m. for the foreseeable future, provided they bring proof of residency.
Sample the best cocktails in Chicago
Whether you’re treating yourself to brunch in Chicago, kicking back on a Chicago patio, or enjoying drinks out at one of Chicago’s many bars and restaurants, you can be sure a finely-crafted cocktail is only seconds away.
Read our full list of the best places to buy cocktails in Chicago.
Kick back at a revered brewery
If craft beers are more your style than a fruity cocktail, worry not—Chicago has an abundance of internationally acclaimed breweries, and it’s one of the best things to do in Chicago in August.
Frequently recognized as one of the best beer cities in the country, our seasoned and inventive beer scene has produced so many fantastic breweries and taprooms in Chicago that we’re spoilt for choice.
There are now over 200 breweries, big and small, across Chicagoland, offering plenty of opportunities to enjoy a finely crafted beer in a range of different environments, regardless of the weather.
Buckel up for a Drunk Shakespeare show
On the topic of booze, another brilliant Chicago experience comes in the form of a live Drunk Shakespeare show.
On a stage in a hidden speakeasy located behind the Chicago Theater, guests will find a glamorous cocktail bar and library featuring over 10,000 books. Five classically trained actors meet as members of “The Drunk Shakespeare Society.” One of them has had at least five shots of whiskey, and then they (quite over-confidently) attempt to perform a major role in a Shakespearean play!
Grab tickets to a Drunk Shakespeare show.
Enjoy a pool at a rooftop
Although Lake Michigan is practically in everyone’s backyard, we sometimes need an escape from the unpredictable, boundless waves for something more serene, and that’s when we can look to higher ground.
From luxurious hotels to member-only clubs, one of the best things to do in Chicago in August is to lie out on a rooftop pool. Finding the right one can be tricky, but luckily, we’ve put together a guide to our favorite hotels with rooftop pools.