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The Chicago Weekend Guide August 16-18

The Chicago Weekend Guide August 16-18

  • The SociaLifeChicago Weekend Guide is your blackbook for weekend fun in the city

From Friday through Sunday, we know you don’t even want to think about work but rather looking for a fun distraction to occupy your weekend in the city, help is here. Whether you want to explore new haunts in Chicago, relax, take in a festival, or have a night out on the town that’ll make your snapchat and insta stories get #FOMO, here’s what to get into this weekend. It’s #summertimeChi so there’s a lot taking place this weekend but these are the recommended ones for  you to go either solo or with a group for a good time. The Chicago Weekend Guide for August 16-18.


WHAT :: Happy Hour at Mata Traders

WHERE :: Mata Traders Headquarters | 5112 N. Ravenswood Avenue  
WHEN :: Friday, August 16 Drop in anytime between 4-8 pm
Stop by Mata Traders, the fair trade ethical clothing company this Friday to preview their spring ’20 collection! There will be snacks and drinks come out.

COST :: Free to attend. Click here for more inf

WHAT :: Eleven Madison Park’s Head Bartender, Matt Hunter @ CAA’s Cherry Circle Room

WHERE:: Chicago Athletic Hotel| 12 S Michigan Ave., Chicago 
WHEN :: Friday August 16 | Starting 5pm
WHY:: As part of Chicago Tribune’s Food Bowl, NYC’s Eleven Madison Park’s Head Bartender, Matt Hunter, will be taking over the bars in the James Beard award-winning Cherry Circle Room and Milk Room at the Chicago Athletic Association Hotel for two nights. Matt will be making signature Eleven Madison Park cocktails as well as a special menu of cocktails exclusive for the evenings. Guests will have the opportunity to talk with him about his cocktail philosophy, Eleven Madison Park, and his relationship with Chicago.
COST :: Attendance is free. Reservation highly encouraged Click Here for more info



WHAT :: Chicago Westside Music Festival

WHERE :: Douglas Park | 1401 South Sacramento Drive
WHEN :: Saturday Aug. 17 | 2:00 PM – 9:00 PM
WHY:: The 8th Annual Westside Music Festival will feature performances by Chicago native DaBrat and Crucial Conflict as well as Faith Evans and Monifah.
COST :: FREE to attend Click here for more info here.


WHAT :: Sangria Festival

photo credit:

WHERE :: 3021 W Division St
WHEN :: Saturday August 17 and Sunday August 18 | 8am
WHY:: Sip Sangria in the Park, while experiencing food bites from locals, live music stage and cultural entertainment that will take you on a tropical paradise journey. Enjoy ethnic live music, flamenco and samba dancers, much more with friends at Chicago’s 4th year of Sangria festival bringing together the art of Sangria paired with a variety of Chicago’s Favorite Eats.
COST :: $15 – $95 Click here  for more info 


WHAT:: White Out Scholarship Bash

WHERE :: SX Sky Bar | 808 South Michigan Avenue
WHEN :: Saturday August 17 | 3-8pm
WHY :: The 100 Black Men of Chicago, presents their 4th Annual Scholarship Fundraiser & White Party! It’s Chicago’s premier “White Party.” We’re taking it up a notch this year, as we host the 100’s very first day party. Live, laugh and dance all while investing in the future of Chicago’s young people.
COST :: $65.00+ | Click here for more info


WHAT :: Pilsen Fest

WHERE :: Pilsen | 18th Street and Blue Island Avenue, Chicago 
WHEN :: Saturday August 17- Sunday August 18 
WHY:: This outdoor festival drawing an attendance of 60,000, aims to expose the Latino community to the deep pool of cultural talent that exists in the Pilsen neighborhood and the Chicago metropolitan area, including musicians, chefs, mixologists, poets, muralists, painters, writers, documentarians, and photographers. The objective of the Festival is to celebrate and embrace diversity, solidarity and unity. 
COST ::  |  Click here  for more info 


WHAT:: Air & Water Show

Where to Watch Guide is right here

WHEN :: Saturday August 17 & Sunday August 18
WHY :: The guide to the fun and fab places to catch the Air & Water Show wether you want to be indoors in comfort or outdoor.
COST :: varies | Click here for more info


See Also

WHAT:: 1060 Block Party

WHERE :: Gallagher Way | 808 South Michigan Avenue
WHEN :: Saturday August 17 & Sunday August 18 | 1PM
WHY :: a Free, all-ages two-day community block party for lovers of music and outdoor grilling. (Re)discover music from Chicago bands curated by Metro Chicago and enjoy upscale eats and flame flavored meats from Gallagher Way eateries.e.
COST :: Free admission | Click here for more info



WHAT :: Roller Dance Fitness at CAA 

WHERE :: Chicago Athletic Hotel 
WHEN :: Sunday August 18 | 11:00AM & 2:00PM
WHY :: Roller Dance Fitness continues is still going with this month’s focus: Whirls and Twirls! Each 90-minute session covers proper skating and safety skills while zeroing in on classic roller dance techniques, inviting you to perform them with confidence and rhythm. All experience levels are welcome and encouraged.
COST ::  Click here for more information

WHAT :: South Shore Summer Festival 2019

WHERE :: South Shore Cultural Center 
WHEN :: Sunday August 18 | 2:00 PM – 8:00 PM
WHY :: The 71st Street/Stony Island Special Service Area (#42) through the support of 5th Ward Alderman Leslie Hairston, will host more than 15,000 residents of the South Shore Community at its annual celebration, the South Shore Summer Festival. This will be a day to enjoy the soulful sounds of local and national musical artists like Robin Thicke and the South Shore Drill team, the neighborhood’s favorite foods, and opportunities to shop with small businesses from both South Shore and surrounding communities.
COST :: Free admission  Click here for more information

Check out this video from a segment on The Jam TV talking about things to do for the weekend. Thank you so much for the opportunity to The Jam Team. Follow them on social and watch daily 6-8am.


Whatever you get into this weekend, tag us on Instagram @SociaLifeChicago with #MakeTheScene. If you’ll be outdoors for a long duration of time, remember sunscreen and hydration (water not just alcohol). Have a great weekend!

*featured image credit: Choose Chicago

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