31 Best Things to Do in Chicago and the Suburbs in August 2023

Those sweet summer days we’ve waited for all year long are flying by. 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.

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All Month

No Man’s Land

After an evening of drink and laughter, the wealthy, aging Hirst and his acquaintance Spooner find themselves taken aback by the arrival of two “sinister” younger men. “A generational power struggle, a tug of war between expert wordsmiths, a maze of murky meaning. Or perhaps it’s just two old English sots waxing nostalgic and waiting for the sun to rise.” Catch this show while you can, performing at Steppenwolf July 13 – August 20, find more details at No Man’s Land.

1650 N. Halsted St.

Murder, Rewrote

This month, the Den Theatre is bringing an “affectionate musical parody of a certain well-known syndicated TV show” to the stage. When a widowed mystery writer and her nephew Grady visit a faded movie star’s mansion and uncover a crime, it’s up to them to find the murderer! This interactive, wickedly entertaining ​​show runs from August 10 – September 16. Grab your tickets now at the Den Theatre online.

1331 N. Milwaukee Ave.

Disney’s Beauty and the Beast

The tale as old as time comes to Chicago this summer, showing at Chicago Shakespeare Theater July 14 – August 20. Join Belle, the Beast and all their companions for this wondrous, 75-minute musical that has won the hearts of families for decades. Don’t miss your chance to swoon to the music and wonder of these beloved Disney songs — ticket reservations can be made at Chicago Shakespeare Theater.

800 E. Grand Ave.

The Empire Strips Back: A Burlesque Parody

Join in the sultry fun of this unique event — The Empire Strips Back: A Burlesque Parody — and let it “deliver you to the dark side.” Walking the line between humor and indulgence, the show promises to thrill its guests as beloved characters are given an exciting revamp that will leave you “laughing and swooning at the same time.” Tickets are on sale now for this 18+ show — which runs through August 13 at the Logan Square Auditorium  — find yours at The Empire Strips Back online.

2539 N. Kedzie Blvd.

Live @ Lighthouse

The immersive exhibits at Lighthouse Art Space have brought thousands flocking to see the interpretations of legendary artists the likes of Mozart, Frida Kahlo and Vincent van Gogh. In a new exploration, join them for a live concert series where rotating musical guests will entertain audiences to the backdrop of moving images. Indulge in the multi-sensory experience — running on Thursdays until the end of August — and buy your tickets while you still can, find them at Lighthouse Art Space.

August 3-6: Lollapalooza

Live music lovers from near and far know that summertime in Chicago also means Lollapalooza, the epic, 4-day festival that draws thousands to Grant Park every year. Headliners this year include Kendrick Lamar, Billie Eilish, Red Hot Chili Peppers and so many more talented acts. All ticket packages — from single day tickets to 4-day passes — are still available on the Lollapalooza website. What else can we even say to convince you? Secure your tickets now!

August 4: Festa Italiana Naperville

All things Italian are happening in Naperville this August as they celebrate the Festa Italiana. Authentic food — including a meatball eating contest — beautiful music, and Italian spirit will be alive at the fest that is welcome to all. Spend the day absorbing the culture and spend the night dancing away to tunes from the old country. Ticket prices vary, more information can be found on the Festa Italiana event page.

523 S. Webster St., Naperville

August 4-6: LeakyCon

LeakyCon is the home for all things fantastical and fandom-related. Fans of beloved characters from tales such as The Lord of the Rings or Harry Potter will want to jump at the chance to meet their idols, commune with fellow fans, attend a variety of programming and more. The opportunities are endless at this weekend-long celebration — head over to the LeakyCon site where you can get your tickets and marvel at what is to come.

McCormick Place, 2301 S. King Dr.

August 4-9: Dancing in the Streets

Over in West Town, the vast beer scene mixed with a little live music, dancing, food from local vendors and more has all combined to become “Dancing In The Streets.” The event is named after a popular Grateful Dead song, and was specifically hosted to coincide with the week dedicated to celebrating the memory of Jerry Garcia. While it is specifically suited for Dead Heads, lovers of good music and good beer will be just as pleased. Visit West Town’s site for entry specifics and updates.

Hubbard Street between Paulina and Wood

August 5: Bronzeville Neighborhood Jazz Fest

The Bronzeville Neighborhood Jazz Fest is bringing the power of music back to the community this summer. The fest is curated by music producer Frank Goss III and the will pay homage to the historical neighborhood of Bronzeville, which is known by locals and other music legends for its rich history and impact on jazz and blues music. For a full lineup of artists and what else to expect at this festival, visit the Bronzeville Neighborhood Jazz Fest online.

Martin Luther King Drive from 39th to 37th

August 5: GUAC

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After Manuel Oliver lost his son, Joaquin, to gun violence he went to work answering the question: What do you do when you lose a son? In this production — called a “one-man tour-de-force” — the story centers on a father turned activist, his undying love for his son and the story of an immigrant family “confronted by a uniquely American Nightmare.” You can catch GUAC for one night only at the Greenhouse Theatre; tickets can be found on their website.

2257 N. Lincoln Ave.

August 5-6: Thirsty Ears Festival

Can you believe Chicago only has one classical music street festival? And that title belongs to the Thirsty Ears Festival, held annually in Ravenswood, where attendees can expect two days of stellar music, craft beer, food trucks, community vendors and kid-friendly activities. Featured acts include ensembles and soloists performing music from Beethoven to Reich and more. Find all information at Access Contemporary Music online.

Wilson street between Hermitage and Ravenswood

August 7-12: Titan Walls Mural Festival

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Returning for its 5th year, the Titan Walls Mural Festival will wow attendees with a collection of murals from 17 globally renowned and emerging muralists. The fest, known as Chicago’s largest mural festival, will be held at District Brew Yards — presented by art activation agency Muros. But folks aren’t coming out for the art alone, enjoy music, food, drinks, sponsored events, giveaways, interactive family-friendly fun and way more while you’re there — and stay tuned for the launch of their immersive exhibit. Details and tickets can be found on the Titan Walls website.

August 9: Keep Stepping

Cinema/Chicago returns this month with the latest installment of their free Summer Screenings series. This month, the film “Keep Stepping” will be shown, which follow dancers as they train and compete in Australia’s largest street dance competition. Over the course of several years, the film details “the multicultural, passion-filled subculture and tells a moving story about love, obsession, and the transformative power of dance.” The 90-minute film will be shown at the Chicago Cultural Center, head over to Cinema/Chicago for more.

78 E. Washington St.

August 10: 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 11-13: Retro on Roscoe

What has been dubbed a “Generation X haven” will include a weekend of classic tunes from various bands; some great food and drink; a classic car and motorcycle show; art vendors; and so much more. Get groovy with your community at this fest that takes up six blocks of Roscoe Village with three concert stages. There is a $15 suggested donation fee, additional information can be found on the Retro on Roscoe event page.

2000 W. Roscoe St.

August 12: Boats and Brews

As part of their ongoing mission to get people out enjoying nature, Friends of the Chicago River is hosting a Boats and Brews event. Meet at the Little Calumet Boat Launch at 1 p.m. where paddling with a tour guide will commence until 3:30 p.m. where guests will then head over to the Blue Island Beer Company for a tour and tasters. All equipment is provided, however, space is limited so if you want to secure your spot, head over to Friends of the Chicago River online to register.

Jackson St. and Aulwurm Dr.

August 12: Bud Billiken Parade

For 94 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 Bud Billiken Parade online for event and route details.

August 12-13: Northalsted Market Days

Celebrating its 41st consecutive year in what is formerly Boystown, the Northalsted Market Days is a weekend filled with live music, drag performances, 250+ 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 13: Andersonville Vintage Market

If you fancy a vintage find, head to the Andersonville Vintage Market, which will include more than 20 vendor stalls showcasing their antique goods over the course of the weekend. Also featured at the market is live screen printing by Anchorfish and treats from Windy City Shaved Ice. There are only a few dates left this summer, so don’t miss your chance. See the lineup of participating stores on the Andersonville Chamber of Commerce website.

1500 W Catalpa, between Clark and Ashland

August 13: 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? Visit the festival yourself, but not before visiting the Bloody Mary Fest website for more details.

Everts Park, 111 North Ave.

August 18-20: Ribfest

Though barbeque may not originate from our Midwest city, that doesn’t mean we don’t know a thing or two about it. And for that reason, Ribfest returns to Chicago for its 23rd year this month. 3 days, 20+ vendors, an anticipated 60,000+ people and a whole heck of a lot of smoked meat goes into making this fest what it is. Held in the NorthCenter neighborhood, entry is only a suggested $10 donation. Want to more info? Visit Ribfest online to know before you go.

Lincoln Avenue between Irving Park Road and Berteau Avenue

August 18-20: Glenwood Avenue Arts Fest

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 19-20: Chicago Air & Water Show

The beauty of Chicago’s blue skies meeting the clear waters of Lake Michigan at the horizon creates a picturesque scene from the shore. 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 19-20: Bulls Fest

Once again, the Chicago Bulls are bringing their annual Bulls Fest back to the United Center for the youth of Chicago. Those who attend will be able to participate in youth clinics, 3v3 games, photo opportunities and more, not to mention meeting legends from the team and Benny the Bull himself. The fest’s schedule is jam packed with fun activities that kids will love — visit the Chicago Bulls website for event details and team registration.

United Center, 1901 W. Madison St.

August 19-20: The Great American Lobster Fest

A nice lobster roll and a cool beverage 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. 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 20: PorchFest Roscoe Village

Calling all music lovers, the Roscoe Village neighborhood is hosting a PorchFest concert series, wherein local musicians from different genres set up on the porches of some of the neighborhood’s favorite houses and play their tunes from 1-5pm. Be sure not to miss this unique, musical event where community connection meets artistic expression. Program specifics can be found on the Lakeview Roscoe Village website where tickets can also be purchased.

Between Addison to Wellington and Ravenswood Ave. to Western Ave.

August 25-27: Taste of Greektown

Greektown is hosting the city’s largest celebration of Hellenic culture by putting a spotlight on popular Greek restaurants during Taste of Greektown. Aside from feasting on Greek specialties, guests can also enjoy live music and entertainment, unique vendors, family friendly activities and more. Whether new or a Chicago favorite, these restaurants — many of which are family owned — would love your support. Visit the Greektown website to find participating vendors and event logistics; stay tuned for updates.

Halsted from Adams to Van Buren

August 25-27: 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 26-27: Lakeview Taco Fest

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Returning for its 10th delicious year, the Lakeview Taco Fest is in full swing this month ready to slay your cravings. This year, there are eight local eateries competing for “Chicago’s Best Taco” and the winner is decided by the attendees. Sample delicious classics like chicken, steak or chorizo tacos, or try something new like mushrooms, goat or duck. No matter what you choose, enjoy yourself with a cold beverage while perusing the other festival events — such as Mexican wrestling and a kids’ zone. Sounds far too good to pass up; get all the logistics on the Lakeview Roscoe Village site.

3500 N. Southport Ave.

August 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 four-day fest actually spills over into September, but real fans know the event 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.

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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.