5 Things to do this Weekend: September 27

The city is packed with exciting events and activities to enjoy as the leaves change and the weather cools. From outdoor festivals and farmers’ markets to cozy fall treats and pumpkin patches, there’s no shortage of ways to experience the season. Take a look at these five events to plan your weekend!

Groove at Hyde Park Jazz Festival 

Experience a day filled with jazz performances featuring renowned artists and local talents. Hosted at various venues, this event offers a range of styles and interpretations of jazz music. Attendees can enjoy food and drinks from local vendors while enjoying interactive activities and workshops for all ages.

Date: September 28-29 
Time: Sat 1:30PM-6:30PM; Sun 2PM-6PM 
Cost: $10 Suggested Donation 
Location: Various Locations 
More Info: hydeparkjazzfestival.org  

Get Bratty at St. Al’s Oktoberfest

St. Al’s Oktoberfest has plenty to offer, including face painting, games, and more. Enjoy traditional Oktoberfest fare such as beer, brats, and pretzels, along with the ceremonial keg-tapping of the legendary Golden Keg and a Stein Hoisting Competition. Top it all off with live music and beer tasting.

Date: September 27-29 
Time: Fri 5PM-10PM; Sat 12PM-10PM; Sun 12PM-7PM 
Cost: Free 
Location: St. Alphonsus Catholic Church, 1429 W Wellington Ave 
More Info: stalsoktoberfest.org

Have Fun at St. Helen Carnival 

Now in its 18th year, this three-day event offers a variety of rides, live music, and delicious food. Attendees can enjoy a selection of cold beers and a mix of family-friendly activities from live music to different carnival rides, offering something for everyone to enjoy.

Date: September 27-29 
Time: Fri 5PM-10PM; Sat 12PM-10PM; Sun 12PM-8PM 
Cost: Free 
Location: 2347 W Augusta Blvd 
More Info: sthelenchicago.org

Paint the Town at Beverly Art Walk

Celebrate art and music at this event that showcases local artists’ home studios and cultural work across Beverly and Morgan Park. This family-friendly event features nearly 150 artists in over 40 venues, along with the popular Uprising Craft Market. Enjoy live music, public art installations, and a painting festival too.

Date: September 28 
Time: 12PM-5PM 
Cost: Free  
Location: Various Locations 
More Info: beverlyarts.org

Find Treasure at Randolph Street Market Festival

Explore a wide array of art, antiques, vintage decor, fashion, and jewelry at this European-style flea market festival. This unique market includes bars, cabanas, and a beaux-arts building, along with live band performances each day. 

Date: September 28-29 
Time: 10AM-5PM 
Cost: $5+ 
Location: 1341 W Randolph St  
More Info: randolphstreetmarket.com

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