August 15th – 18th: Sangria Festival, Chicago Caribbean Carnivale, and More Fun Things to Do this Weekend

This weekend, meet some of the most influential women in fashion at the Dream Big Curvy Conference. Sip over 20 different Sangria’s at the Sangria Festival. Walk/Run for a good cause with My Block, My Hood, My City 1st Annual Community Run. Experience Caribbean culture at the Chicago Caribbean Carnival 2019. Check out these events, plus more fun things to do in Chicago this weekend below.


Dream Big Curvy Conference

Saturday | August 17th | 6:00 p.m.

Venue Six10 | 610 S Michigan Ave.| $25

Dream Big Curvy Fun Things to Do this Weekend in Chicago
Image | Dream Big Curvy Conference

Meet some of the most influential women in the fashion and lifestyle space at this weekend at the DREAM BIG Midwest Conference. This conference is where curvy fashion and beauty enthusiasts are paving their way through the industry while empowering a culture of confident curvy women. Tickets include parties, workshops, panels, networking, and more. Grab specially priced tickets from The Haute Seeker by following this link. For more details on this curvy-focused conference, visit the website here.

Spring Collection Preview & Shop Mata

Friday | August 16th | 4:00 p.m. – 8:00 p.m.

Mata HQ | 5112 Ravenswood Ave. | Free

Mata Traders Things to Do this Weekend in Chicago
Image | Mata Traders

Make your Friday night a very fashion-forward one at Mata HQ. The fair-trade shop, offering an array of handmade women’s clothing, previews their spring collection this weekend in Chicago. Shop the racks and survey the new items at the headquarters in Ravenswood. For more details, visit the Facebook page.

Food + Drink: 

Sangria Festival Chicago

Saturday – Sunday | August 17th – 18th | 12:00 p.m. – 10:00 p.m.

3021 W Division St | $15 – $95

Sangria Festival Fun Things to Do this Weekend in Chicago
Image | Sangria Festival

Sip Sangria and enjoy sweet tunes at the 4th Annual Sangria Festival this weekend in Chicago. “Salud!” With friends over food bites from locals, live music stage and cultural entertainment that will take you on a tropical paradise journey. Enjoy live ethnic music, flamenco, and samba dancers, much more. Tickets to the fun event include a variety of over 20 flavors of Sangria plus a complimentary souvenir sangria glass (while supplies last) and two drink tickets. To purchase tickets, visit the Event page.

Taste of Diversity 2019 at Center on Halsted

Thursday | August 15th | 11:00 a.m.

Center on Halsted | 3656 N. Halsted Ave. | $30

Taste of Diversity Center on Halsted Fun Things to Do this Weekend in Chicago
Image | Center on Halsted

Experience foods from different culinary landscapes at the Taste of Diversity this weekend in Chicago. Join the chefs, alumni and students of the Center on Halsted’s Silver Fork culinary arts and job readiness program as they present tasting samples from a diverse cultural landscape as well as tasty bites from community partner restaurants. Tickets include food tastings, complimentary wine, beer, and soda. To purchase your tickets to the event, visit the website.


My Block, My Hood, My City 1st Annual Community Run

Sunday | August 18th | 8:00 a.m. – 12:00 p.m.

Marquette Park | 6743 S Kedzie Ave. | Free

My Block, My Hood, My City 1st Annual Community Run featured in August Events Guide 2019 on The Haute Seeker
Image My Block, My Hood, My City

Run or walk for a good cause with other Chicagoans during the first annual My Block My Hood My City 5K. As featured in the August Event Guide, the 5K takes place at Marquette Park and includes a view of 323 scenic acres on the city’s South West Side. Experience a race day featuring live music, a history hunt, and prizes for top runners and top fundraising teams. To participate as a volunteer or as a runner/walker during the race, visit the event page here.

Arts + Culture:

Chicago Caribbean Carnivale 2019

Saturday | August 17th | 10:00 a.m. – 9:00 p.m.

Midway Plaisance | 60th and Ellis| Free

Chicago Caribbean Carnivale Fun Things to Do this Weekend in Chicago
Image | Chicago Caribbean Carnivale

While the Caribbean may be over 1,500 miles away from Chicago, this weekend it gets just a little bit closer. The Chicago Caribbean Carnivale is fun, family friendly, all day festival featuring authentic Caribbean food, arts & crafts, vendors, and most importantly, a road parade. Experience the global celebration right here in the Midwest. For more details on the parade and other events celebrating Caribbean culture this weekend, visit the event page.

Chicago Air and Water Show

Saturday – Sunday | August 17th – 18th | 10:00 a.m. – 3:00 p.m.

Fullerton to Oak Street | Free

61st Annual Chicago Air and Water Show  featured in August Events Guide 2019 on The Haute Seeker
Image | Chicago DCASE

Enjoy the largest free show on land and sea this weekend. The Air and Water show is a free non-stop event full of action on North Avenue Beach. The event features military and civilian flight aerobatics, historic aircraft, simulated water rescues, and parachute teams. Be sure to catch this fun event taking place this weekend by visiting the website here.

What I’m Seeking:

Hi Fellow Seekers! This weekend I will be in Las Vegas for work! See what I am seeking while I am out of town by following me @The Haute Seeker on Instagram.

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