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!
1. Attend Lollapalooza
Taking place August 1st–4th, 2024 this year, Lollapalooza is one of Chicago’s beloved music festivals. The major headliners include SZA, Tyler, The Creator, Blink-182, The Killers, Hozier, Skrillex, and more. The annual music festival is one of the best things to do in chicago in August.
2. 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, Chicagoans flock to the downtown area and line up on bridges and along the riverwalk to watch the spectacle. 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 upwards of $300,000 for over 20,000 athletes and more than 10,000 young athletes.
Read more about the Chicago Ducky Derby here.
3. 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 2024 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 until 2 pm on August 10 – 11, 2024.
Read more about the Chicago Air & Water Show.
4. 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 19, and Sunday, August 20.
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.
5. 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 pm and every Wednesday at 9 pm 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.
Read more about the weekly Navy Pier fireworks shows.
6. 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 throughout the week offer midweek plans featuring live DJs, unobstructed views of the skyline, and the chance to make memories as the sun sets on Lake Michigan.
7. 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 highrise 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.
Read more about Chicago kayaking.
9. The ‘World’s Largest Karaoke’ at the Salt Shed
The ‘World’s Largest Karaoke’ will take place on August 8, 2024, at The Salt Shed Outdoors (Fairgrounds). The event will be from 5:00 PM to 10:00 PM, with doors opening at 5:00 PM. To sing, you must sign up for the event. Those who sign up will be entered into a random selection.
10. Check out London House’s “Luminescence” experience
London House Chicago, a luxury hotel known for its unmatched sweeping views of the Magnificent Mile and the Chicago River, has revived its summer “Luminescence” experience on its famed 22nd-floor terrace.
The award-winning rooftop hosted its inaugural edition of the 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.
11. See the world-famous umbrella sky project
London House Chicago is far from the only place to find a kaleidoscope of color this month. One of the best things to do in Chicago though is not strictly in Chicago. The Umbrella Sky Project art installation has taken over Elmhurst, filling the sky with bright floating umbrellas.
The prismatic art installations are only staying up for summer, so it is worth getting out there when you can and taking in the canopy of color!
Read more about the Umbrella Sky Project.12. Wander Morton Arboretum’s new range of sculptures
A new exhibition at the Morton Arboretum has opened, featuring a collection of towering arbor-inspired sculptures. Titled “Of the Earth,” the exhibition features five exclusive new works from Polish-American artist Olga Ziemska and replaced those on display for Human + Nature.
The largest exhibition of artist Olga Ziemska’s work to date, “Of the Earth,” has been created exclusively for Arboretum visitors. According to an official Morton Arboretum release, Ziemska’s sculptures have been predominantly created from reclaimed tree branches and other natural materials gathered from various locations throughout the Arboretum’s grounds.
Read more about the arboretum’s ‘Of the Earth’ exhibition.
13. 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 be performing at extraordinary venues all over 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.
14. Get rowdy at a festival
Chicago summers get pretty busy—between concerts, food, and neighborhood festivals, it’s almost impossible to keep up with what’s happening in the city. One of the best things to do in Chicago is heading to a festival! We’ve created this list, so you’ll never miss out on whatever you are drawn to—country music, house music, vintage shopping…it goes on.
Read more about all the festivals happening in Chicago this August.
15. 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.
16. 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.
See all the concerts happening in Chicago in August.
17. 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.
18. 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.
19. 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 the average underwhelming Tuesday into a jubilant evening at the MCA’s Anne and John Kern Terrace Garden, experiencing 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.
Read more about Tuesdays on the Terrace.
20. 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.
Retro on Roscoe takes place from Friday, August 11 until Sunday, August 13. Admission is a $15 suggested donation.
Read more about Retro on Roscoe.
25. 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.
26. 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.
According to the Art Institute of Chicago website, admission will be free for Illinois residents on Thursday evenings, 5–8 pm until August 31, 2023.
27. 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.
28. Spend a Sunday at Maxwell Street Market
Maxwell Street Market, Chicago’s longest-running open-air market, first debuted in 1912 and has returned for its 111th summer stretch with handmade crafts and undetected treasures.
Open every Sunday at 800 South Des Plaines Street from 9 am to 3 pm through to Sunday, October 29; shoppers can expect a Sunday of spirited live music and sensational street food as well as an eclectic array of bric-à-brac.
Read more about Maxwell Street Market.
29. Dine at lovely weekend brunch
If you’re in need of an instant mood boost, searching for a group Sunday Funday activity, or looking to cure a hangover from the night before, brunch is the solution to all problems.
Luckily Chicago has an abundance of seriously good morning eats, and here we’ve compiled the best of the bunch!
Read our full list of the best brunch spots in Chicago.
30. 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.
From top-notch margaritas to more innovative cocktail concoctions and everything in between, the Windy City and its abundance of revered mixologists have the answers to whatever it is you’re after.
We’ve recently filtered through the noise to round up the best cocktail bars in Chicago based on our experiences at Secret Chicago, our reader’s most popular choices, and a scrupulous assessment of settings and drink quality.
Read our full list of the best places to buy cocktails in Chicago.
31. 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 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, meaning there are plenty of opportunities to enjoy a finely crafted beer in a range of different environments, whatever the weather.
To ensure you’re checking out the best of the best, we’ve rounded up the 10 best breweries, brewpubs, and taprooms in Chicago. Cheers!
32. 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 behind the Chicago Theater, guests will find a glam cocktail bar and library with 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!
Hilarity and mayhem ensue while the four sober actors try and keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
Grab tickets to a Drunk Shakespeare show.
33. Peruse the magnificent street art murals of Chicago
Chicago’s street art and graffiti scene has continued to thrive in Chicago over the last decade. New pieces pop up all over the city every week, some of which are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now part and parcel of the Windy City’s identity.
Today murals do more than provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for racial equality, celebrate different heritages, and honor the essential workers of our societies during turbulent times. Hunting down the must-see street art murals in Chicago is a rewarding experience any time of the year.
We’ve rounded up our top 25 most amazing murals in Chicago so you can navigate your way around the best of the best and learn about its history and the inspiration behind some of Chicago’s famous murals.
Alternatively, you can also jump on an Offbeat Street Art Tour of Chicago and be guided by a seasoned street art enthusiast!
34. 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 lay 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.
Read our guide on Chicago’s best rooftop pools.
35. Head out of the city and see Illinois’ natural spectacles
One of the best things to do in Chicago in August is to see stunning natural spectacles in Illinois. If you enjoy being surrounded by nature, then heading out to the quiet of Illinois’ natural beauty is a great year-round experience.
Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible spectacles this time of the year. From monolithic marvels to cascading waterfalls, here are seven natural wonders of Illinois that you can visit while they’re about to peak:
- Garden Of The Gods: Saline County
- Wildcat Canyon In Starved Rock State Park: La Salle County
- Cache River State Natural Area: Johnson County
- Cave-In-Rock: Hardin County
- The Pomona Natural Bridge: Jackson County
- Cascade Falls In Matthiessen State Park: La Salle County
- Bork Falls In Ferne Clyffe State Park: Johnson County
Read more about the natural wonders near Chicago.
36. Watch the Art on TheMART projections
One of the truly uniques one of the best things to do in Chicago in August is combining kayaking with the Art on the MART projections.
Holding the title of the largest permanent digital art projection in the world, Art on theMART attracts thousands to the Riverwalk every week by firing up 34 digital projectors and showcasing work from both renowned artists and local talent on the 2.5-acre river façade of the Merchandise Mart.
The summer program began in July and features mesmerizing projections by the Chicago Black Dance Legacy Project as well as the continued Building Light projections every night through mid-September.