45 Fun Things to Do in Chicago in August

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 name events like Lollapalooza and the Air and Water Show attract visitors, and it is one of the busiest times of 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.

Please note that this post contains affiliate links. I may earn a small commission for my honest recommendations, at no additional cost to you.

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 31-August 3, 2025

Lollapalooza is one of the biggest events of summer in Chicago. The four-day festival books more than 170 artists in genres including indie, pop, hip-hop, and electronic. Don’t miss my Lolla tips to have the best fest experience!

4. Jeff Fest  – August 1-2, 2025

Head to the Northwest Side for food and fun at Jeff Fest in Jefferson Park. Rock out with Lucky Boys Confusion, Rearview: Pearl Jam Tribute, and more.

5. Bronzeville Smooth Jazz Fest – August 2, 2025

Corey Wilkes, Harlan Jefferson, 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. Bears Family Fest – August 3, 2025

Storm Soldier Field with the whole family for Chicago Bears Family Fest. Watch the Bears practice, play family friendly activities, and get your photo with Staley Da Bear from 10 a.m. to 2:30 p.m.

8. Touring Chicago’s Lakefront with Geoffrey Baer – August 6, 2025

Join Chicago’s favorite history buff for an outdoor screening of Touring Chicago’s Lakefront with Geoffrey Baer at Navy Pier. Learn about Chicago’s beaches, harbors, and waterfront and ask him your questions during a Q&A. Check out my appearance on his Chicago Mysteries special!

9. Margarita Fest on the Beach – August 7, 2025

Soak up every minute of summer with a salty marg in your hand at the Margarita Fest on the Beach. Shore Club at North Avenue Beach hosts three hours of margarita and giveaways on the shore of Lake Michigan.

10. Windy City Comedy Fest – August 7, 2025

Chicago’s comedy scene is legendary, the Windy City Comedy Fest features comedians from across the country. The three-day festival takes place at iO Chicago in Lincoln Park and features hilarious talent like host Rebecca Joey Schwab, Chris Cyr, Christine Ferrera, and Queeny Bitch.

11. Chicago Ducky Derby – August 7, 2025

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’s 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 8-10, 2025

Celebrate Chicago’s LGBTQ+ community at Northalsted Market Days street fest. Five stages feature drag, dance, and live music performances from artists like Keke Palmer and Saucy Santana.

14. Dancing In The Streets – August 8-10, 2025

How many beers until you start dancing? Dancing in the Street highlights West Town’s beer scene in the Chicago Brewing District. Enjoy dancing, live music, and beer from like On Tour Brewing Company, Midwest Coast Brewing Company, and more local brewers.

15. Sabor Taco Y Tequila Festival –  August 8-10, 2025

If you want to sample some of the best tacos in Chicago, Pilsen should be your first stop. Sabor Taco y Tequila Fest features varieties like carnitas, al pastor and vegan options. Add live music and tequila cocktails and you’ve got a vibrant street festival!

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 here.

17. Bud Billiken Parade – August 9, 2025

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 96th Annual Bud Billiken Parade & Back to School Festival’s theme is “Road to 100 Years,” honoring cultural pride.

18. Taste Of Chicago Albany Park – August 9, 2025

The iconic Taste of Chicago comes to Albany Park for one day of free, family-friendly entertainment throughout the weekend. Stop by from 12-8 p.m. with performances including American Indian Center Drum & Dance and the Chicago Immigrant Orchestra. Sample more than 15 food vendors like Arepa George and Star of Siam.

19. Printers Row Art Fest – August 9-10, 2025

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. LatiNxt Festival – August 9-10, 2025

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

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 15-17, 2025

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 two stages of performers including The O’My’s, Pictoria Vark, and Smut.

23. Air and Water Show – August 16-17, 2025

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 August 16-17 with rehearsal on August 15.

24. Chicago Mural Fest – August 16, 2025

Watch art in action at the Chicago Mural Festival in the South Loop. More than 18 artists will paint live-action murals while DJs play music transforming public spaces into a canvas.

25. Great American Lobster Fest – August 16-17, 2025

What’s better than the Air and Water Show? The Air and Water Show with lobster! Put on your lobster bib and head to Navy Pier for the Great American Lobster Fest. Crack open fresh Maine lobster and listen to live music as the Thunderbirds zoom overhead.

26. Morton Wine & Art Walk – August 16-17, 2025

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

27. StoryBoard Writers Fest – August 16-17, 2025

StoryStudio Chicago presents the 8th annual StoryBoard Festival at the Newberry Library. Writers can develop their craft, learn about publishing, and take classes at this two-day festival.

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. Wine Fest on the Beach – August 21, 2025

Sip some wine with your toes in the sand at Shore Club on North Avenue Beach. Wine Fest on the Beach offers three hours tasting several varieties of wine.

30. Lakeview Taco Fest – August 22, 2025

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 22, 2025

Greek culture and cuisine take center stage at the 35th Annual Taste of Greektown
Celebrate 35 Years of Hellenic Pride at 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 22-23, 2025

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 22-24, 2025

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. Noche Caribeña – August 23, 2025

Dance to Puerto Rican music on the shore of Lake Michigan at Noche Caribeña. The free concert at Navy Pier blends Puerto Rican, Afro-Caribbean, Latin American, salsa, bomba, and plena performances.

35. West Loop Art Fest – August 23, 2025

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 23, 2025

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. Sangria Festival – August 23-24, 2025

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.

38. Chicago Triathlon – August 23-24, 2025

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 ends in Grant Park

39. Chicago Jazz Fest – August 28-31, 2025

Chicago is a renowned jazz city, and the Chicago Jazz Fest celebrates this legacy. The free festival in Millennium Park highlights local and international talent like Monty Alexander, Patricia Barber, and Patricia Barber.

40. North Coast Music Fest – Aug 29-31, 2025

North Coast Music Festival celebrates its 15th anniversary with electronic music talent like Kaskade, Sofi Tukker, and Zeds Dead. The beat drops at SeatGeek Stadium in Bridgeview, IL during Labor Day Weekend.

41. ARC Music Festival – August 29-Sept 1, 2025

House and techno music fans pack Union Park in the West Loop for ARC Music Festival. The three-day festival includes performances by Eric Prydz, Jamie xx, and Amelie Lens.

42. Taste Of Polonia Festival – August 29-Sept 1, 2025

You don’t need to be a member of Chicago’s proud Polish community to enjoy the Taste of Polonia Festival at the Copernicus Center. Stop by Jefferson Park for Polish cuisine, beer, and performances along with a Kids Zone.

43. African Festival of the Arts – August 30-Sept 1, 2025

Ring in Labor Day weekend with Labor Day weekend, with the African Festival of the Arts at the DuSable Museum. More than 100 curated vendors offer art, food, crafts, and live music from across the Diaspora.

44. Bike the Drive – August 31, 2025

Once a year, Chicagoans have the unique opportunity to ride their bikes on DuSable Lake Shore Drive. Bike the Drive allows you to ride as much of the 30-mile course as you like with views of Lake Michigan and the Chicago skyline.

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 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 in 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 wearing a breezy linen dress in hot weather. Here’s a sleeveless linen dress that you can dress up or down and one with short sleeves and pockets (of course!).
• My warm-weather uniform is comfy linen shorts and a Merino wool t-shirt or tank top 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.
• 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 throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May
• What to Do in Chicago in June
• Fun Things to Do in Chicago in July
• What to Do in Chicago in September
• What to Do in Chicago in October
• Fun Things to Do in Chicago in November
• What to do in Chicago in December