Haute & Cool Things to Do This Weekend in Chicago

This weekend embrace the cool temps and warm up with incredible things to do around the city of Chicago. Enjoy fall festivals in Lincoln Square or fabulous eats from local favorites in the West Loop. There is plenty to sip, explore, and enjoy this weekend in Chicago.

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

Apple Fest in Lincoln Square

Saturday, October 1st – October 2nd // 9:00 a.m. – 6:00 p.m.

Cost: Free Admission

Usher in the Fall with the Lincoln Square Ravenswood Chamber of Commerce’s 35th Annual Apple Fest! Apple Fest is a long-standing tradition in Lincoln Square, bringing the community together to celebrate the beginning of autumn. Sample sweet and savory options from over 20 local food vendors, activities, and more during this free family-friendly event in Chicago.

Taste of Fulton Market Things to do Chicago The Haute Seeker

Taste of Fulton Market

Thursday, September 29th // 5:00 p.m. – 9:00 p.m.

Cost: $75 – $105

Taste of Fulton Market is back again for a second year with the continued goal of providing community support to the IRAEF’s Restaurant Employee Relief Fund and Recipe for Change while celebrating the vast and exciting talent of the Fulton Market Dining District.

Tickets to this event include a cocktail and a sampling of food items from Fulton Market’s exemplary bevy of bars and restaurants. In addition to the great food and drinks, various local sponsors will be onsite providing fun, interactive activities like a photo booth, glass etching, and a silent auction.

Ragamala: A Celebration of Indian Classical Music – Celebrating 10 Years

Friday, September 30th – Saturday, October 1st // 6:00 p.m. – 7:30 a.m.

Cost: Free

As part of the 2022 World Music Festival Chicago, the Chicago Cultural Center will host Ragamala: A Celebration of Indian Classical Music – Celebrating 10 Years. The most extensive all-night-long presentation of live Indian classical music in the United States. Enjoy the rare opportunity to hear the ragas (traditional scales or modes) during the early morning and late-night hours as they were meant to be played. This event is free with no tickets or advanced registration.

Ragamala Things to do Chicago The Haute Seeker
pumpkin patch at Indian boundary park Chicago things to do weekend The Haute Seeker

Harvest Fest at Indian Boundary Park

Sunday, October 2nd // 10:00 a.m. – 2:00 p.m.

Cost: Free

Looking for fun things to do with the family this weekend? Find the perfect pumpkin at the Harvest Fest sponsored by the Chicago Park District. Pick and personalize your own personal pumpkin at the on-site pumpkin patch. Guests can also enjoy carnival-themed games, inflatables, a harvest photo station, and kid-friendly live entertainment.

There will be a $5 fee for the pumpkin. Everything else is free.

Giveon Chicago

Sunday, October 2nd // 8:00 p.m.

Catch R&B superstar artist Giveon this weekend in Chicago. The HEARTBREAK ANNIVERSARY singer will take the stage at the Byline Bank Aragon Ballroom for his 2022 Give Or Take Tour.

Giveon Chicago Things To Do Chicago The Haute Seeker

The Future is Black AF – Madison & Pulaski Redefined

Saturday, October 1st // 1:00 p.m. – 5:00 a.m.

Cost: Free

Join TRUdelta, Project Forward, the Black Culture Collective, and Trap House Chicago for informational and community discussion aboutThe K, a business incubation hub and cafe coming to the Madison & Pulaski Corridor in 2023.

Learn about local community groups organizing to create safe spaces for Black families through the long-term lens of entrepreneurship and how you can contribute to the overall social and financial wellness of the community on the West Side of Chicago.

Andersonville Arts Weekend

Friday, September 30th – Sunday, October 2nd // Time Varies

Cost: Free

Find something unique during Andersonville Arts Weekend. The fall festival showcases Andersonville’s strong connection to the arts community featuring over 40 local businesses and 100 artists participating across several genres. Attendees can enjoy a self-guided Art Walk during the day and parties at night while, exploring the neighborhood’s unique shops and restaurants and seeing how they have transformed into galleries.

Chicago WingOut

Saturday, October 1st – Sunday, October 2nd // 12:00 p.m. – 8:00 p.m.

Cost: $14 – $79

Sample some of the best wings the city has to offer during WingOut in Chicago. WingOut Chicago is an outdoor, chicken wing block party, offering all-you-can-eat wings from the top vendors in the city. Held in the St. Michael’s in Old Town parking lot, patrons can indulge in a variety of flavors, like Classic Buffalo to Asian Ginger, while also enjoying adult beverages and live music.

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

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