45 Fun Things to Do in Chicago in August from a Local

If you like hot days packed with festivals and special events, then August is one of the best times of the year to visit Chicago. The city is buzzing with everyone cramming their bucket list activities into the last days of summer and maximizing their time in Chicago’s parks, beaches, and lakefront. Big events like Lollapalooza and the Air and Water Show attract visitors, and it is one of the busiest times of the year in the city. Now is the time to enjoy a rooftop cocktail, swim in Lake Michigan, and eat grilled food at a street festival.

I’ve lived in Chicago for nearly two decades, and I’ve written two books about Chicago. I find that August is one of the liveliest times in the city. Whether you’re visiting Chicago in August or you live in Chicagoland, here are 45 fun things to do in Chicago in summer.

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Fun Things to Do in Chicago in August

1. See a Show in a Historic Speakeasy

The Drifter is no Prohibition-themed bar, it is a hidden room that actually served as a speakeasy in Prohibition-era Chicago! Learn the history of Chicago’s authentic speakeasy and how to find the entrance to the Drifter.

2. Raise a Glass on a Booze Cruise

There’s no feeling like raising a glass from the water as you sail past downtown Chicago’s iconic architecture. Choose from a classy meal on the Premier Brunch Cruise or more of a Sunday Funday atmosphere on a tiki boat Bloody Mary Party Cruise.

3. Rock Out at Lollapalooza – July 30-August 2, 2026

Lollapalooza is one of the biggest events of summer in Chicago. The four-day festival books more than 120 artists in genres including indie, pop, hip-hop, and electronic. Don’t miss my Lolla tips to have the best fest experience!

4. Italian Beef Fest – July 31-August 2, 2026

The first annual Italian Beef Fest replaces Jeff Fest as the premier summer party in Jefferson Park. Head to the Northwest Side for food and fun all weekend in Jefferson Memorial Park.

5. Bronzeville Smooth Jazz Fest – August 1, 2026

Park n Ride, Reggie Foster, Willie Fultz, and more play the free Bronzeville Smooth Jazz Festival. The family-friendly event features food trucks and artists at Mariano’s Bronzeville.

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

6. See the World of Devil in the White City

You’ve read the book, now step into the past with the Chicago Architecture and True Crime History Tour inspired by Devil in the White City. The 90-minute tour will guide you through the city’s architectural highlights and darkest true crime stories.

7. Free Fitness at Navy Pier

Get your sweat on every Tuesday night at Navy Pier with free fitness sessions all summer. Pier Fitness encourages you to feel the burn with classes ranging from Zumba to sunset yoga.

8. Tour the Chicago River with Geoffrey Baer – August 2, 2026

Join Chicago’s favorite history buff for the Chicago River Tour with Geoffrey Baer. Learn about Chicago’s architecture, history, and waterfront while you cruise. Check out my appearance on his Chicago Mysteries special!

9. Summer Screenings – Through August 22, 2026

Enjoy free films all summer, programmed by the Chicago International Film Festival. Summer Screenings spotlights a film from a different nation each week throughout the summer at the Chicago Cultural Center and the Chicago History Museum. In honor of the Route 66 centennial, this year’s theme is the “road movie.”

10. Windy City Comedy Fest – August 6-9, 2026

Chicago’s comedy scene is legendary, but the Windy City Comedy Fest features comedians from across the country. The four-day festival takes place at several venues around town and features hilarious talent like Isabel Hagen, Bob Keen, and 50 more comedians.

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11. Chicago Ducky Derby – August 6, 2026

Thousands of rubber ducks will take to the Chicago River on the Columbus Drive Bridge at 1 p.m. at the Chicago Ducky Derby. Spectators will adopt around 100,000 rubber ducks to raise money for Special Olympics Illinois in a thrilling spectacle for a great cause.

12. Set Sail on a Tall Ship

There are a lot of boats on Lake Michigan, but only one Tall Ship Windy. Raise the sails and feel the wind in your hair on this 90-minute cruise.

13. Market Days – August 7-9, 2026

Celebrate Chicago’s LGBTQ+ community at Northalsted Market Days street fest. Five stages feature drag, dance, and live music performances from artists like Keri Hilson, Dawn Richard, and Frankie Grande.

14. Ravenswood Feel Good Fest – August 8, 2026

Feel good and do good with the community at Ravenswood Feel Good Fest. This new block party highlights wellness, sustainability, arts, and community organizations for all ages and abilities. Join the fun starting at 11 a.m. near the Black Ensemble Theater on Sunnyside Ave. west of Clark Street.

15. Bud Billiken Parade – August 8, 2026

The largest African American parade in the nation steps off in Washington Park from 10 a.m. to 4 p.m. before a festival in the park. The 97th Annual Bud Billiken Parade & Back to School Festival’s theme is “Road to 100 Years,” honoring cultural pride.

16. Visit Chicago’s Oldest Monument

Take a drive down to the Southeast Side of Chicago and admire the city’s oldest monument. The little-known marker on the Illinois and Indiana border dates back nearly two centuries to 1833. Learn more about Chicago’s oldest monument and watch me give Geoffrey Baer a tour of it..

17. LatiNxt Festival – August 8-9, 2026

Latin culture is in the spotlight at this vibrant festival at Navy Pier. The free LatiNxt Festival features contemporary Latin music, art, and food.

18. World’s Largest Karaoke – August 15, 2026

Sing your heart out at the World’s Largest Karaoke at Salt Shed. Attendees will attempt to break the reigning world record and gather 5,000 singers to take the stage. The free event goes down from 4 to 10 p.m.

19. Printers Row Art Fest – August 15-16, 2026

Charming Printer’s Row is the perfect setting for the Printer’s Row Art Fest. Admire work from 95 artists around the country, get a personalized poem, and stroll to neighborhood restaurants.

20. Get Spellbound at a Trickery Chicago Magic Show

Bored of barhopping? Prepare to be amazed by a Trickery Chicago Magic Show. The theater is BYOB, but they provide cups and bottle openers if you bring a beverage to enjoy. The hour-long show is a fun way to kick off your night, and you’ll be wondering how they did that for days!

21. Take a Dip at a Rooftop Pool

Pool access is a great excuse to book a staycation. In the Gold Coast, the Viceroy Hotel delivers skyline views while the Hoxton Hotel offers them from a West Loop vantage. If you want to sit poolside while still admiring Lake Michigan book a room at the Radisson Blu Aqua Hotel in the Loop. The Robey Hotel’s sixth-floor pool may be tiny, but it is open to the public. For a more affordable staycation, the DoubleTree MagMile boasts a Streeterville pool at approachable rates.

22. Glenwood Avenue Arts Fest – August 14-16, 2026

Home to a creative community with art lining the streets and two theater companies, the Glenwood Avenue Arts District hosts the Glenwood Avenue Arts Fest. Enjoy artists, food vendors, and two stages of performers in Rogers Park.

23. Air and Water Show – August 15-16, 2026

U.S. Air Force Thunderbirds zoom overhead, and U.S. Army Parachute Team Golden Knights drop from the sky at the free Chicago Air and Water Show. The action is centered around North Avenue Beach from 10:30 a.m. to  3 p.m. on Saturday and Sunday, with rehearsal on Friday. Don’t miss my Chicago Air and Water Show Tips for a High-Flying Weekend!

24. Morton Wine & Art Walk – August 15-16, 2026

Spend a lovely summer day strolling the Morton Arboretum, sipping wine, and admiring nature-themed artwork. Peruse arts like woodwork, photography, ceramics, jewelry, and more artworks created by Midwest artists at the Wine and Art Walk.

25. StoryBoard Writers Fest – August 15, 2026

StoryStudio Chicago presents the 9th annual StoryBoard Festival at the Newberry Library. Writers can develop their craft, learn about publishing, and take classes at this festival.

26. Galewoodstock – August 22, 2026

Ready to get groovy? Head to the Galewoodstock Music Festival on the city’s west side! The sixth annual neighborhood festival delivers live music, arts vendors, and kids’ activities to its diverse community at Bloomingdale and Sayre from 12-9 p.m.

27. Evanston Art & Big Fork Festival – August 22-23, 2026

Get artsy in nearby Evanston at the free Evanston Art & Big Fork Festival. Browse works from150 juried artists ranging from paintings to sculpture to jewelry, get a personalized poem written, and get creative with the little ones at the Kids Art Zone before chowing down on fare from local food trucks.

28. Visit Northerly Island’s Secret Beach

With skyline views and lakefront walking trails, Northerly Island Park is one of the most beautiful parks in Chicago in summer or winter. It’s also home to a little-known beach at 12th Street Beach where you can enjoy the blue waters of Lake Michigan without the crowds.

29. Cool Off with Ice Cream Classics

There are delicious ice cream shops across Chicago, but only a couple have lasted more than a century. The Original Rainbow Cone began serving a colorful combination of sliced ice cream in Beverly way back in 1926. While it has expanded to more locations and ice cream trucks around town, I like to visit the original Western Avenue location once a summer. In Logan Square, you’ll find a line stretching outside of Margie’s Candies. Even the Beatles loved this Chicago classic. Read more about it: Margie’s Candies: Chicago’s Sweet Spot.

30. Lakeview Taco Fest – August 21-23, 2026

The Southport Corridor transforms into the Lakeview Taco Fest, featuring more than 10 local restaurants competing for the title of best taco. Vote for your favorite taco, enjoy live music, and cheer on a lucha libre match.

31. Taste of Greektown – August 28-30, 2026

Greek culture and cuisine take center stage at the 36th Annual Taste of Greektown. Greek dishes from Athena Restaurant, Mr. Greek Gyros, and 9 Muses Bar & Grill will have you saying “Opa!”

32. Chicago House Music Festival and Conference – August 27-30, 2026

Celebrate a Chicago original in the city that invented House Music. The free Chicago House Festival features DJs playing the revolutionary dance music in Millennium Park.

33. Edison Park Fest – August 28-30, 2026

Edison Park Fest brings the street festival to the Northwest Side. Bring the family and enjoy live music, bingo, a bike parade, and a carnival for classic summer fun.

34. Sangria Festival – August 15-16, 2026

Sangria takes center stage at the Sangria Festival Chicago. Raise a glass in Humboldt Park where sangria is paired with Latin-inspired cuisine, dancing, and live music.

35. West Loop Art Fest – August 22-23, 2026

Stroll four art-filled blocks on Fulton Street at the free West Loop Art Fest. More than 100 artists from around the country will be exhibiting their work in a variety of mediums.

36. Chalk Howard Street Fest – August 22, 2026

Get creative at Chicago’s only chalk art festival! Rogers Park hosts the Chalk Howard Street Fest featuring professional chalk artists, family-friendly entertainment, live music, and a kids’ chalk area.

37. Tour Frank Lloyd Wright Architecture in Oak Park

Oak Park boasts more Frank Lloyd Wright homes than any other city in the world and visiting them is a must for any architecture fans. This Frank Lloyd Wright Oak Park Architecture Tour will pick you up in Chicago and take you on a half-day, private tour that is personalized to your interests. Learn about Wright’s life in Oak Park, his early career, and his influential designs. You’ll visit the Frank Lloyd Wright Home & Studio, Unity Temple, and more from the father of the Prairie style.

38. Chicago Triathlon – August 22-23, 2026

Enjoy the unique experience of competing in a triathlon that takes place in and along Lake Michigan. Even if you’re not competing, cheer on contestants at the Chicago Triathlon starting at Lake Michigan and ending in Grant Park

39. Argyle Night Market – August 27, 2026

Don’t miss the last Argyle Night Market of the summer. Taste your way through Uptown’s restaurants at this free street festival highlighting Asian street food while watching live music and cultural performances. The party goes down on Argyle Street between Kenmore and Sheridan from 5-9 p.m.

40. Edgewater Music Fest – Aug 28-30, 2026

New music fest alert! The first Edgewater Music Fest features more than 30 artists, including Ted Leo and the Pharmacists, Maps & Atlases, and Lowdown Brass Band. Browse more than 80 local vendors on Broadway between Thorndale & Ardmore.

41. Summer Block Party at Navy Pier – August 26, 2026

Cap off the season with Navy Pier’s Summer Block Party. Be amazed as breakdancers face off in a competition, groove to live music, and join in on family-friendly activities. The free event ends with a dazzling fireworks display on Lake Michigan.

42. Panda Fest – August 28-30, 2026

Celebrate the diversity of Asian cuisine at Panda Fest in Grant Park. Get a ticket for this outdoor festival to experience more than 200 Asian street food vendors, Asian cultural performances, Asian merchandise vendors, and plenty of panda-themed activities.

43. Big Grill Fest Chicago – August 29-30, 2026

Barbecue is taking over Wrightwood Park for Big Grill Fest Chicago. Grab a ticket and head to Lincoln Park to chow down on live-fire dishes by chefs from around the U.S. and as far as Brazil and London. I can already smell the grilled meats!

44. GoodWaves Festival – August 30, 2026

Who doesn’t love a free music festival? Goodwaves Music Festival is an all-ages event that goes down outdoors at the Salt Shed Fairgrounds. Seeing Killer Mike, Snow Tha Product and more on a summer day is the perfect way to cap off the season.

45. Light it Up at London House’s “Luminescence”

Reserve a table for a front-row view of colorful, floral LED installations on the London House Hotel rooftop. In addition to the blooming lights of Luminescence, London House has one of the best rooftop views in Chicago.

Visiting Chicago in August FAQ

Is August a good time to visit Chicago?

August is the busiest month for visitors in Chicago. With hot weather, long days, hot weather, and big-name events, August is a fun month to visit Chicago. If you plan on visiting iconic attractions like the Field Museum, Art Institute, and Skydeck Chicago I recommend booking tickets in advance. Due to the elevated number of visitors in the city, you should book flights and hotel deals ahead of time as well as reservations at top restaurants. Whether you’re attending big events like Lollapalooza or the Air and Water Show or simply enjoying the lakefront, it doesn’t get better than August in Chicago.

What is Chicago weather like in August?

August in Chicago is typically hot and humid. According to the National Weather Service, the average temperatures in Chicago in August range from a high of 82 degrees to a low of 65 degrees. Expect sunshine with humid conditions and occasional rain showers. Chicago is known for its rapidly shifting weather, so check the forecast before you visit Chicago in the summer.

What should I wear to Chicago in August?

If you’re wondering what clothes to wear to Chicago in August, pack for hot, sunny weather. I recommend packing shorts, dresses, and comfortable shoes. Rain is always a possibility during summer in Chicago. Check the weather forecast before you visit Chicago in August so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the summer.

• I love a linen dress in hot weather. Here’s a linen dress that you can dress up or down and one with short sleeves and pockets (of course!). This set is super versatile too!
• My warm-weather uniform is comfy linen shorts and a Merino wool t-shirt that wicks sweat to keep you dry on hot days.
• Chicago is a walking town, so pack comfortable shoes like sneakers, or sandals. 
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped shirt that I didn’t like.
• It doesn’t hurt to pack a windproof travel umbrella for rainy days.

Where to Stay in Chicago in August

Wondering where to stay overnight in Chicago in the summer My favorite hotel views are from the Chicago Athletic Association overlooking Millennium Park and the boats on Lake Michigan and the LondonHouse with jaw-dropping views of the Chicago River from the rooftop bar. I love the views of Grant Park from the Blackstone Hotel and the Hilton Chicago. Some of my favorite hotels stays in Chicago are at the luxurious Four Seasons Chicago and Waldorf Astoria Chicago located near the best shopping and dining in the Gold Coast area.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you plan your trip to visit Chicago in August!

Find out what to do in Chicago all year. Click on any month to plan your perfect day in the Windy City.
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