8 Fun Things To Do In Chicago This Weekend: Sept 23–24, 2023

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Chicago, a vibrant metropolis known for its rich history, stunning architecture, and diverse culture, offers a plethora of exciting activities to make your weekend a memorable one. Whether you’re a foodie, an art enthusiast, a nature lover, or simply looking for some family-friendly fun, Chicago has something special in store for you. In this guide, Let us take you through a handpicked selection of fun things to do in Chicago this weekend, ensuring that your visit to this iconic city is nothing short of spectacular. So, pack your bags and get ready to dive into the heart of the Midwest’s cultural gem!

Check Out The Exciting Things To Do In Chicago This Weekend



Get ready for a gastronomic extravaganza like no other as Chicago Gourmet 2023 returns to the iconic Millennium Park from September 21 to 24. This annual culinary celebration is a food lover’s paradise, showcasing the very best of Chicago’s vibrant culinary scene and welcoming renowned chefs, sommeliers, and food enthusiasts from all over. Indulge in a gourmet weekend filled with delicious tastings, cooking demonstrations, wine seminars, and so much more.
When:- Thu Sep 21 2023 at 07:00 pm to Sun Sep 24 2023 at 05:00 pm (GMT-05:00)
Where:- Various locations across Chicago — 205 E Randolph, Chicago, United States
More Info:- https://allevents.in/chicago/chicago-gourmet-2023/10000558296739577


Dust off your lederhosen and prepare for a barrel of fun because Oktoberfest Chicago is back, bringing the lively spirit of Germany’s most famous festival to the heart of the Windy City. Get ready to raise your steins, dance to lively music, savor delicious German cuisine, and immerse yourself in a celebration like no other.

When:- Fri Sep 22 2023 at 05:00 pm to 10:00 pm (GMT-05:00)
Where:- 1429 W Wellington Ave, Chicago, IL 60657–4121, United States
More Info:- https://allevents.in/chicago/oktoberfest-chicago/200024882888146


When:- Fri Sep 22 2023 at 09:00 pm to Sat Sep 23 2023 at 03:00 am (GMT-05:00)
Where:- V Live Restaurant & Live Music Entertainment, 2501 South Kedzie Avenue, Chicago, United States
More Info:- https://allevents.in/chicago/los-monstruos-del-rock-mexicano-fest-chicago-il/10000684395464257


Chicago Latina Expo 2023 focuses on providing Latinas with the tools to break down the systemic barriers that prevent them from achieving social and economic mobility. This Expo will explore health wealth business systemic racism and equality, aiming to create more opportunities for Latinas to succeed in the boardroom and in their lifestyles.

When:- Fri Sep 22 2023 at 10:00 am to Sat Sep 23 2023 at 04:00 pm (GMT-05:00)
Where:- Malcolm X College, 1900 W Jackson Blvd., Chicago, United States
More Info:- https://allevents.in/chicago/chicago-latina-expo-2023/80001547072527


Get ready to dive into an autumn wonderland at Sonny Acres Farm for our highly anticipated Fall Festival in West Chicago! Prepare yourself for non-stop family fun as you explore a thrilling array of attractions and amusements. From the adrenaline-pumping Wacky Worm Roller Coaster to the delightful Sonny Express Train to picking the perfect pumpkin in our West Chicago Pumpkin Patch — there’s something to enchant everyone in the family.

When:- Fri Sep 22 2023 at 10:00 am to 06:00 pm (GMT-05:00)
Where:- Sonny Acres Farm, 29W310 North Ave., West Chicago, United States
More Info:- https://allevents.in/west%20chicago/fall-festival-event-at-sonny-acres-farm-west-chicago-il/80003414586258


Get ready to shake it off and sing along to your favorite Taylor Swift hits at the Taylor Swift Drag Brunch Chicago — the ultimate fusion of fabulous drag performances and a delectable brunch experience that’s bound to leave you enchanted. This one-of-a-kind event invites you to step into a world of glitz, glamour, and all things Taylor Swift.

When:- Sat Sep 23 2023 at 11:00 am to 04:00 pm (GMT-05:00)
Where:- The Walnut Room Chicago, Chicago, United States
More Info:- https://allevents.in/chicago/taylor-swift-drag-brunch-chicago/200025163966602


Join Small Business Expo and Networking Event as companies showcase and/or sell their products, provide demonstrations with informational handouts, offer free samples, or provide discounted deals. Mix & mingle with other business professionals that are serious about growing their network. Develop professional relationships in a professional environment.

When:- Sat Sep 23 2023 at 11:00 am to 03:00 pm (GMT-05:00)
Where:- Chicago, United States
More Info:- https://allevents.in/chicago/small-business-expo-and-networking-event-chipopup/10000527945849247


Welcome to the 17th Annual Hyde Park Jazz Festival. Enjoy this free two-day celebration of jazz, creativity, and community on the South Side of Chicago. This Festival was created in late 2006 when cultural leaders on the South Side met with the Hyde Park Jazz Society to develop an annual event that would bring new audiences into the many arts and culture venues in Hyde Park and celebrate jazz’s great legacy and bright future on Chicago’s South Side.
When:- Sat Sep 23 2023 at 12:00 am to Sun Sep 24 2023 at 12:00 am (GMT-05:00)
Where:- Hyde Park, Chicago, IL, United States
More Info:- https://allevents.in/chicago/17th-annual-hyde-park-jazz-festival-%7C-music-in-chicago/2200025422222702

 Also Read: Explore Best of Events in Chicago this Weekend 2023
Location: Chicago, IL, USA

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