Chicago is a city that’s always bursting with fun, innovative, and often free things to do.  And August may just be the best month of summertime Chi yet. We want to make sure that you don’t miss the most essential events. Here are 10 Events we definitely think you should look out for. 

Soulful Chicago Book Fair- Saturday, August 3-  61st Street between Cottage Grove and King Drive 

Black literature gets its due at this annual festival featuring 1000s of titles from Black authors. Two stages of entertainment, international food, author talks, literary workshops and more await.  With 4 city blocks of books and entertainment, Soulful Chicago Book Fair will have something for everyone.  Admission: FREE

Black Ballerina, August 10-25, Fleetwood- Jourdain Theatre 927 Noyes St, Evanston

For some of us, the ride to Evanston can be quite the trek, but for this event-we think it’s worth the drive. According to its website, Black Ballerina is the story of “A stunning Black ballerina dreams of fulfilling her lifelong passion to dance the iconic roles in the world of classical ballet, but like the Black ballerinas of the past, she has to confront some profound realities while fighting for the right to dance.  Teeming with original music and beautifully choreographed ballet performances, Black Ballerina is a story that must be told and seen.” Evanston native and professional ballerina Kara Roseborough and Chicago actor Shariba Rivers will star.  For tickets, visit here.

Craft Cocktail Festival, Thursday August 15 2019, Westfield Old Orchard 4905 Old Orchard Su. 066 Skokie

Alright cocktail lovers- this is going to be the best 25 dollars you spend all week. Not only will it get you 10 craft cocktail samples, andgenerous food samples from participating retailers including: Nando’s PERi-PERi, Hampton Social, Roka Akor Old Orchard, and more, but 100% of the proceeds will go to Fight2Feed, an organization that’s “fighting hunger with rescued food and mobilizing to get it to hungry friends in need.”

Find more information and purchase tickets here

Bronzeville Art District Trolley Tour, Fri, August 16, Gallery Guichard 436 E. 47th Street

Love Black Chicago has attended the Trolley Tour and the experience was fantastic. If you attend you will be trollied to five different art galleries around Bronzeville with a tour guide who will tell you everything that you need to know about the galleries and their owners. You’ve heard of tours around downtown Chicago, so why not support one in one of the most historic and soulful neighborhoods of Chicago? The trolley tour will not disappoint. Expect food, drinks, and awesome music as well! It seriously makes for a fabulous night that celebrates and honors a great part of black Chicago. Oh and by the way, this event is free! 

Be sure to look out for our story on the 13th annual Bronzeville Art District Trolley Tour which runs every 3rd Friday through September.

Books, Bourbon, and Basquiat, August 16, Semicolon Bookstore 515 North Halsted Street

Enjoy specially curated bourbon-based cocktails. small bites, premium bourbon samples and conversations on art, literature and more.  Tickets are available at Eventbrite.

Westside Music Festival, August 17,  Douglas Park, Chicago

Since 2012, the Westside Cultural Foundation has brought us the Westside Music Festival, and this year is bigger than ever! Known for its 90s R&B/Hip Hop flavor, WMF returns with Monifah, Chicago’s own Da Brat and Crucial Conflict, and headliner Faith Evans.  Chicago native Sandy Redd of The Voice will also make an appearance. It is a free event (you know we’ve got you with the free events) and is open to all ages. Go for a day of music, food and entertainment.. We hope to see you there.

Chicago Caribbean Carnivale Parade & Festival, August 17, Midway Plaisance Park 1130 Midway Plaisance Park

Witnessing the beautiful Carnivale celebrations in the Caribbean is a dream for many. Well, get ready to save a lot of time on an airplane because Carnivale is coming to the Chi! This free event will celebrate tradition, culture, food, music, and unity. Don’t miss your chance to celebrate Carnivale in your own backyard! Find more information here.

South Shore Summer Festival 2019, August 18, the 71st Street/Stony Island Special Service Area

This is one that music lovers will not want to miss.  Chicago’s 7th Annual South Shore Summer Festival is a free event that will showcase local and national musical artists including headliner, Robin Thicke! This festival is not exclusive to music. There will be food, and small business vendors, giving you an opportunity to support the South Shore neighborhood. This event is going to huge and is expected to host more than 15,000 residents of South Shore and surrounding neighborhoods so don’t miss out! 

41st Annual Jazz Festival, August 23rd-September 1, MIllennium Park and Chicago Cultural Center.

For jazz lovers this is a 10-day festival where you can take advantage of free performances in neighborhood clubs and venues from August 23 to 29, leading up to the concerts beginning Thursday, August 29, at Millennium Park (201 E. Randolph St.), Chicago Cultural Center (78 E. Washington St.) and other citywide locations through Sunday, September 1.

To catch as much Jazz as you can— head over to their website for the schedule and locations of all of the awesome performances. 

PearlFest 2019, Saturday, August 24, Little Black Pearl Oakwood/39th Street Beach

I know what you’re thinking- there can’t be more free events on this list, can there? Yes there are, and this one is epic!  In celebration of Little Black Pearl’s 25thAnniversary, PearlFest returns with a bang.  The slew of heavyweight talent includes Robert Glasper, Avery Sunshine, Lizz Wright, Terri Lyne Carington and the legendary Nona Hendryx.  Food, fun and fabulous music is on deck at what will definitely be one of the hottest events of the summer.  And its FREE for lawn seating, or you can upgrade to VIP. 

Find out more at their website.

August is packed with fun events to take advantage of, show us how much fun you are having this summer by tagging us on Instagram or Facebook @loveblackchicago for a chance to be featured on our page! We love to hear from you and cannot wait for you to visit our top ten events of August. 

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