Haute & Cool Things to Do This Weekend in Chicago

This weekend is all about higher vibrations in Chicago. Join fellow music and art lovers at a series of events across the city. From Pilsen Art Fest and live performances by DVSN to the 40th Anniversary of Smartbar and an open house at Bridgeport Art Center, there is so much to explore this weekend.

Check out the full guide of Haute and Cool things to do in Chicago this weekend below.

Season Opening: Fall Festival at Sonny Acres Farm

Saturday, September 17th // 10:00 a.m. – 5:00 p.m.

Cost: Pricing Varies

Find the perfect pumpkin this Saturday at the opening of Sonny Acres Farms. The iconic family-friendly festival begins September 17th for a limited time through October 30. In addition to finding the perfect pumpkin, enjoy a variety of amusements and attractions including everything from the Wacky Worm Roller Coaster to a ride around the property on the Sonny Express Train. Take fun to new heights our giant jumping pillow, get back to nature and feed the farm animals, enjoy great food at our outdoor grill and much more! Stop in at our Farm Fresh Market for produce, sundries and one of a kind decorations.

Pilsen art fest things to do in chicago this weekend by The Haute Seeker

Pilsen Art Fest

Saturday, September 17th – Sunday, September 18th // 12:00 p.m. – 10:00 p.m.

Cost: Free

Celebrate community and culture at Pilsen Fest this weekend in Chicago. This outdoor festival will feature renowned musical acts drawing an attendance of over 50,000 people. The objective of the Festival is to celebrate and embrace diversity, solidarity, and unity. Pilsen Fest will make an incredible impact of putting together a musical lineup, as well as a production plan that is sure to impress attendees, ensuring their loyalty and return for years to come. The following are some bands we have worked with in the past

Women’s Artisan Market

Saturday, September 17th // 1:00 p.m. – 6:00 p.m.

Make this Saturday a fun day out with the girls, mom, daughter, family or friends, and swing by the Women’s Artisan Market in the Irving Park neighborhood of Chicago. Check out great handmade products made by talented women owned businesses. All of the products sold are handmade, unique and won’t see anywhere else. Enjoy some great food, music, conversation and much more. For a full participation of vendors, check out Chicago Handcrafted.

Women's Artisan Market things to do in chicago this weekend by The Haute Seeker
Culture of Curvesthings to do in chicago this weekend by The Haute Seeker

2022 Culture Of Curves Fashion Show

Saturday, September 17th // 3:00 p.m. – 6:00 p.m.

Cost: $65 – $85

Chicago fashion will be in full effect this weekend in the West Loop. Cultures Closet, Chicago’s premier Plus Size Boutique will host their annual “Culture of Curves” fashion show. Don’t miss out on this epic fashion show in Chicago.

Bridgeport Art Center(BAC) Open House

Friday, September 16th // 7:00 p.m. – 10:00 p.m.

Cost: Free

Visit Bridgeport for their monthly open house. There will be two new exhibitions, open studios from resident artists, and work from Project Onward studio.

A Smartbar 40th Anniversary Party

Saturday, September 17th // 10:00 p.m. – 5:00 a.m.

Cost: $25 – $35

Celebrate all things the 40th Anniversary of Chicago’s very own Smartbar with a mix of House, IDM, Breakbeat, and Tech House sets from global artists. Catch Bonobo, Garret David, and Michael Serafini playing hits all night long.

Englewood Music Festival 2022

Saturday, September 17th // 12:00 p.m. – 7:00 p.m.

Cost: Free

The Englewood Music Festival will feature live music, local vendors, back-to-school programming and prizes, community resource fair, art activations, and more.


Saturday, September 17th // 7:00 p.m.

Cost: $25 – $70

Experience the magic of Mykonos in Chicago with Avli Restaurant. The all-white party will feature fire dancers on the rooftop, silent disco, and a mesmerizing and electric musical experience to dance the night away.


Saturday, September 17th // 10:00 p.m.

Cost: $30 – $300

Experience a one-night only performance with Canadian R&B duo DVSN. Listen and party with your favorite artists during this unique music event in Chicago. You never know who or what can happen.

Discover more things to do in Chicago by checking out our events calendars.


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