10 Fun Things to Do in Chicago in August

Updated on August 6, 2018
Natalie Frank profile image

Natalie, a Ph.D. in Clinical Psychology, is a freelance writer who can write on anything she can research. Her interests span the globe.

The winter in Chicago can be brutal, with temperatures frequently dipping below zero and the wind coming in off of the lake making it feel even colder. It’s no wonder that when summer hits, the residents of this city are intent on coming out to play. There are plenty of activities and events that occur in the summertime, and many are concentrated in August to get that last bit of fun in before the weather starts to cool again and the kids go back to school.

So get out your calendars and your Chicago travel guides and mark down these events that are held annually each August in the Windy City. Whether you are a Chicago resident or a visitor, you are bound to find something on the list that you will enjoy.

1. Windy City Rubber Duck Derby

Usually held on the first Thursday of August (although it will be held on August 9th in 2018), a dump truck filled with more than 60,000 rubber ducks drops the huge flock of waterfowl into the Chicago River as spectators cheer their chosen yellow bird on towards the finish line. The event which has been followed by national news stations and magazines including USA Today, ABC News, and Fox News, and raises money for Special Olympics Illinois.

You can adopt one duck for $5, six for $25, two dozen for $100, or 240 ducks for $1,000. The owner of the duck that crosses the finish line first usually wins a vehicle. In 2017, the winner received an SUV. In 2018, the prize is a Chevy Equinox. Other prizes are also awarded such as $2,500 cash, NASCAR tickets, and all-inclusive vacations. Check out the race's website for more info.

2. Lollapalooza

Lollapalooza Music Festival, held annually during the first full week of August, is one of the more popular summer festivals occurring in Chicago. It now runs for four full days since a day was added in 2015 (the 25th Anniversary of the concert).

The concert boasts over 170 different popular bands, so it’s always a hit with the huge number of fans in attendance. Past headliners include Chance the Rapper, Arcade Fire, Blackberry Smoke, The xx, Run the Jewels, the Killers, Justice, Muse, DJ Snake, Lorde, JJ Grey and Mofro and Blink-182. There is food galore, an art market, and special mini-festival experience for the kids.

Tickets start at $120 for general admission with options to upgrade for special opportunities. Children 10 and under are admitted free and allowed to attend all Kidapalooza events. Tickets sell out quickly, so if interested, it’s best to get them early. If the concert is sold out, there are a number of re-sellers you can contact for seats. You can also become an Ambassador and get free admission in exchange for selling Thursday and Sunday tickets.

3. Evanston + Vicinity Biennial

Billed as one of the Midwest's largest and most prestigious juried art exhibitions, this free event usually occurs from August 5th through August 31st. Showcasing Chicago artists, the event is held at the Evanston Art Center. The show includes artworks from all mediums, and many pieces are for sale. The highlight of the event comes at the beginning of the month with an Artists’ Reception, where patrons can meet and talk to the various artists whose works are being shown. Awards are also presented at the reception, including Best of Show and Juror’s Merit.

Past artists have included Robin Dluzen, Riva Lehrer, Timothy McMullen, Ryan Thompson, and Rafael E. Vera. A notable highlight from the 2017 show was a sound installation by Riva Lehrer, Carrie Sandahl, and Christophe Preissing. Galleries are handicapped accessible, and all exhibitions are open to the public.

4. Edge Fest

This annual festival, held the first weekend of August, celebrates the popular Northside neighborhood of Edgewater. With a theme of an outdoor cafe setting, festival-goers can sit and sample the local flavorful cuisine while watching award-winning entertainment. There is also plenty of family fun at this free event. Local musicians play throughout the day, and vendors showcase their wares up and down the main street.

On Saturday, there is a pet parade and competition that has quickly become one of the favorite activities for the young and old. Humans can show off their pets by entering them into one or more of four competitions: best costume, best trick, smallest or biggest pet, and owner and pet look-alike contest. Winners get bragging rights.

Other popular entertainment in past years has included an ABBA Salute, performances by the Second City Outlaws, Boy Band Night, the Chicago Spirit Brigade, School of Rock, and a variety of cultural performances. Visit their site for further information.

Festival goers enjoy a concert at Edge Fest
Festival goers enjoy a concert at Edge Fest

5. Rogers Pork Barbecue Arts and Music Festival

A local Rogers Park festival, held the first Saturday of August rain or shine, this free event draws residents and tourists from all over Chicago. Having grown spectacularly since its beginning in 2013, the Rogers Park festival features art in all mediums, gifts for purchase, and a number of services offered by over 40 vendors. There are also two large stages, one at each end of the concourse where bands perform throughout the festival and, of course, different types of barbecue and numerous other food and beverage offerings. Some of the local establishments that have provided BBQ in the past include Amazing Aaron, R Public House, RIB1.com, BBQ Truck and Three Legged Tacos.

Visitors can choose to buy items from vendors offering pottery, paintings, sculpture, lighting designs, glasswork, jewelry, woodwork, photography and other fine arts, skin care and bath products, fiber designs, candles, and collages, among other types of items.

While the festival is free, a VIP ticket is available for $20, which will provide you with priority seating for concerts, a dedicated bartender providing you with Cava and rosé, and a complimentary glass of wine. Visit their site for more information.

6. Tastemaster Chicago

Touted as the culinary event of the year, Tastemaker Chicago is usually held on the third weekend in August. This is unique event pairs two different chefs together, each pair producing truly one-of-a-kind dishes. The open kitchen houses 8 unique chef collaborations allowing you to sample first time dishes and to talk to these culinary masters as they serve their creations to you personally.

There are four sessions with two collaborations per session. Each four-hour session costs $65, which is all-inclusive. Tickets include food and drink from over 40 restaurants, wineries, breweries, and artisan producers, as well as live entertainment and a variety of activities. Tastemasters is a 21 + event. For $250, Capital One cardholders can attend a pre-opening five-course collaborative tasting menu, which includes a welcome cocktail, full drinks flight, chef meet and greets, and a gift bag.

7. Chicago Air and Water Show

Usually held the third weekend of August, the Air and Water Show is always a big draw. Free to the public both days, this event, the largest free show of its kind in the U.S., viewers can experience daredevil thrills in the air and on the water. The show can be seen from a large area of the lakefront specifically from Fullerton Beach to Oak Street Beach, with North Avenue Beach as the primary viewing location.

The show has featured some of the best civilian and military pilots and most unique aircraft. Some of the repeat headliners have been the U.S. Navy Blue Angels, the U.S. Air Force Thunderbirds, the U.S. Army Parachute Team Golden Knights and the U.S. Navy Leap Frogs. There are also a number of civilian aerobatic teams that perform. Some of the planes that have been included in previous shows include the C-130 Hercules, the KC-135 Stratotanker, P-51 Mustang, and the supersonic T-38 Talon and the U. S. Navy F-18. Other types of crafts often included are the U.S. Coast Guard MH-65 Dolphin Helicopter, the U.S. Coast Guard Cutter and the F-35 Heritage Flight.

All stunts are performed over the water using the most up to date safety guidelines for both the pilots and the audience. With over two million viewers coming out to see the show over the course of the two days, organizers recommend getting there early. Many high-rise restaurants and bars in the area also offer specials during the show.

See all kinds of planes performing aerobatics at the Chicago Air and Water Show
See all kinds of planes performing aerobatics at the Chicago Air and Water Show

8. Windy City West Indian Carnival

This family-oriented cultural event features live entertainment, children’s activities, and authentic Caribbean cuisine. authentic steel pan music and traditional West Indies dance performances. Held the third Saturday of August, the festival explores the culture of the diverse populations of the West Indies and the Caribbean.

The venue is the historic Midway Plaisance on the campus of the University of Chicago. The biggest draw of this dawn til dusk Carnival is Parade of Bands Competition. Carnival goers crowd the streets to cheer for the mas bands as each competes to claim the title of “Windy City Carnival Midwest Band of the Year”. This coveted award is the highest honor that is awarded at West Indian Carnival and bands also compete for the prize money (1st Place $2,500, 2nd Place $1,000, 3rd Place $500). If you are a musician but don’t belong to a band you can join one of the bands already registered to compete.

Performers, along with many carnival goers, dress in elaborate, colorful, handmade costumes, and audience members are encouraged to join in the fun by dancing with the bands in the streets. Take a break from the excitement by visiting dozens of vendors or grabbing a bite to eat.

If you don’t want to fight traffic you can take the round trip Carnival bus for $45 which leaves from a convenient central location. Listen to music mixed by a professional music master, enjoy free food and cocktails, and get a chance to win a prize on each leg of the journey. The event is free, but donations are gratefully accepted.

9. Oak Park Microbrew Review

Held the third Saturday of August, this event features the best craft beers produced by microbreweries in Chicago with selections from others in the Midwest and national craft breweries as well. While sipping on your choice of more than 80 brews you can also sample local food provided by Oak Park restaurants and enjoy live music. This event is billed as one of the Midwest's top craft beer festivals of the summer and the largest zero-waste craft beer fest in the Midwest. Proceeds from the festival go to support Seven Generations Ahead which is an organization dedicated to promoting healthy and sustainable communities locally and nationwide.

General admissions tickets cost $45 ($65 at the gate). For an additional fee, you can buy VIP or Hop Challenge Tickets. Hop Challenge tickets allow you early access to the Hop Challenge area which is a contest for local brewers who are provided with specific instructions they must adhere to when creating their entry microbrew. In 2018 they were required to use a specific type of yeast to produce any type of beer they chose. Hop Challenge ticket holders can sample the entries to their hearts' content and then vote for their favorite with an award given to the winner. A VIP ticket will allow you special access to small venues scattered around the festival which offer special beers paired with small plates of food as well as the Hop Challenge.

The Oak Park Micro Brew Review lets you sample over 80 micro brews from local breweries and around the country
The Oak Park Micro Brew Review lets you sample over 80 micro brews from local breweries and around the country

10. Shakespeare in the Parks

A summer Chicago favorite, Shakespeare in the Parks is a traveling group of performers present 75 minute adaptations of classic Shakespeare tales. The versatile Chicago Shakespeare Theater Company, tours to neighborhood parks across the North, South and West sides of the city from the end of July through most of August. Each summer they mount a different play, which they put on for free, allowing people across the city to have the chance to see it. At each park, a large truck is brought in which houses a full stage with scenery and lighting. The show is intended for audiences of all ages. In the first seven years of the production, over 130,000 people have been able to attend the all free performances. The play for 2018 is A Midsummer Night’s Dream. More information about the schedule can be found at Chicagoshakes.com.

Annual August Festivals and Events Held In and Around Chicago

The list of Festivals here includes those that are thrown regularly each August. The dates given are for 2018, but they fall around the same time each August. Many are free, and some of the rest only ask for a suggested donation that isn't required to enter.

July 25 - Aug. 26 Shakespeare in the Parks (Various)

Aug. 2-5: Lollapalooza (Loop)

Aug. 2-5: Little Italy Fest-West (Addison)

Aug. 3-5: Jeff Fest (Jefferson Park)

Aug. 3-5: Destination Asia Festival (Lisle)

Aug. 4: Rogers Pork Barbecue, Arts & Music Festival

Aug. 4-5: Edge Fest (Edgewater)

Aug. 4-5: Art at the Glen (Glenview)

Aug. 4-5: Chicago Brewing District's Dancing in the Streets (West Town)

Aug. 4-30: Black Harvest Film Festival (Hyde Park)

Aug. 8-26: Chicago Tribune FOOD BOWL (Various locations)

Aug. 9: Windy City Rubber Duck Derby (Loop)

Aug. 10-12: Chicago Hot Dog Fest (Lincoln Park)

Aug. 10-12: Ginza Holiday Festival (Lincoln Park)

Aug. 10-12: Retro on Roscoe (Roscoe Village)

Aug. 10-12: Festival Cubano (Belmont Cragin)

Aug. 11: Bud Billiken Parade (Bronzeville)

Aug. 11-12: Northalsted Market Days (Lakeview)

Aug. 11-12: Lincolnshire Art Festival

Aug. 11-12: Near North Food Truck Social

Aug. 11-12: Thirsty Ears Festival (Ravenswood)

Aug. 11-12: My House Music Festival (Pilsen)

Aug. 12: Slow & Low Chicago Lowrider Festival (Pilsen)

Aug. 13: The Chicago Ice Cream Social (Near North Side)

Aug. 16: Clark After Dark (Near North Side)

Aug. 16-19: Little Italy Festa Taylor St.

Aug. 16-18: Tastemaker Chicago (West Town)

Aug. 17-19: Edison Park Fest

Aug. 17-19: Glenwood Avenue Arts Fest (Rogers Park)

Aug. 17-19: Evanston Art & Big Fork Festival

Aug. 18-19: Chicago Air and Water Show (Near North Side)

Aug. 18-19: Ukranian Days Festival (West Town)

Aug. 18: Windy City West Indian Carnival (Hyde Park)

Aug. 18: Oak Park Micro Brew Review

Aug. 18-19: Sangria Festival (West Town)

Aug. 18-19: Pilsen Fest

Aug. 18-19: Vintage Days (Long Grove)

Aug. 19: South Shore Summer Fest

Aug. 19: Summer Smash (Douglas Park)

Aug. 22-26: Will County Fair (Peotone)

Aug. 24-26: Taste of Greektown

Aug. 24-26: Logan Square Food Truck Social

Aug. 25-26: Port Clinton Art Festival (Highland Park)

Aug. 25-26: Bucktown Art Fest

Aug. 30-Sept. 2: Chicago Jazz Festival (Loop)

Aug. 31-Sept. 2: NorthCoast Music Festival (West Town)

Aug. 31-Sept. 2: Great American Lobster Fest (Near North Side)

Aug. 31-Sept. 3: African Festival of the Arts (Washington Park)

Aug. 31-Sept. 3: Taste of Polonia (Jefferson Park)

Questions & Answers

    © 2018 Natalie Frank

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      • Natalie Frank profile imageAUTHOR

        Natalie Frank 

        2 weeks ago from Chicago, IL

        You are welcome to visit any time, Flourish! Always lots to do especially when the weather warms up given it doesn't stay that way for long! Thanks for the comment.

      • Natalie Frank profile imageAUTHOR

        Natalie Frank 

        2 weeks ago from Chicago, IL

        Yes, Dora, it's amazing how many things there to do here in the summer and in particular, in August! Come by and visit some time!

      • FlourishAnyway profile image

        FlourishAnyway 

        2 weeks ago from USA

        There’s so much to do I don’t see how anyone in Chicago gets bored. Great events that make many of us jealous!

      • MsDora profile image

        Dora Weithers 

        2 weeks ago from The Caribbean

        Wow! There are enough activities in August to make memories for a year. Food and music would be the attraction for me. Thanks for this fun information.

      • Natalie Frank profile imageAUTHOR

        Natalie Frank 

        2 weeks ago from Chicago, IL

        I have to say, Bill, the Rubber Ducky Derby is one of my favorite events all year! I love watching all the ducks hit the water at once. There's something about a dump truck unloading 60,000 of the little buggers into the river at once that makes my heart feel light.

      • Natalie Frank profile imageAUTHOR

        Natalie Frank 

        2 weeks ago from Chicago, IL

        Yes Liz, it is a great place to be in August. I never fail to be stunned by the number of festivals held each summer with them heavily concentrated in August.

      • Eurofile profile image

        Liz Westwood 

        2 weeks ago from UK

        Sounds like a great place to be in August. There's so much going on.

      • billybuc profile image

        Bill Holland 

        2 weeks ago from Olympia, WA

        Very nice! We have a rubber duck race here as well on one of the local rivers...all monies go to charities. Always a fun event.

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