# Things to do in Chicago this weekend (Oct 23–25, 2026)

100 events around Chicago, picked by Thursday Drop. Updated 2026-10-23T17:55:54.848Z. Web version: https://thursday.kandr.io/email/chicago

## Forecast

- Fri: 65°F, Cloudy
- Sat: 68°F, Cloudy
- Sun: 70°F, Cloudy

## Pick of the week

- **IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago**: Sat, Oct 24 · 12pm · Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk), Chicago · See tickets. Tix Start at $5! Enjoy Hayrides on the River, Photo Ops, Live Music, a Pumpkin Patch, Fall Beer, Cocktails & Food, Games & More! [Details](https://thursday.kandr.io/r/70e50187156bfad8?m=chicago&c=seo)

## Live Music

- **Saturday Night Live Chicago!**: Sat, Oct 24 · 10pm · Y Bar, Chicago · See tickets. When the sun goes down, Chicago comes alive. [Details](https://thursday.kandr.io/r/24a6cf9f6890ad4a?m=chicago&c=seo)
- **SATURDAYZ @ MASADA: Afrobeats, Amapiano, Dancehall, R&B**: Sat, Oct 24 · 10pm · Masada, Chicago · See tickets. Voted #1 Afrobeats Dance Party in Chicago [Details](https://thursday.kandr.io/r/7d377c9910eee4f8?m=chicago&c=seo)
- **The Inn Crowd at Hubbard**: Sat, Oct 24 · 10pm · Hubbard Inn, Chicago · See tickets. Come hang out on Saturdays and enjoy drinks, music, and good company for just a dime! [Details](https://thursday.kandr.io/r/d41349bb66b04ca5?m=chicago&c=seo)

## Eat & Drink

- **River North Halloween Bar Crawl 2026**: Sat, Oct 24 · 5pm · Joy District, Chicago · Free. Chicago Halloween Bar Crawl | River NorthSaturday, October 24 | Doors from 5:00pm, bars to 11:30pm | Chicago | 21+ One wristband, every bar on the River North route, and no cover… [Details](https://thursday.kandr.io/r/8eff4ee94bee2eda?m=chicago&c=seo)
- **Chicago Official Halloween Bar Crawl - Lincoln Park - Sat, Oct 24**: Sat, Oct 24 · 5pm · Brando's Lincoln Park, Chicago · Free. Chicago Halloween Bar Crawl | Lincoln ParkSaturday, October 24 | Doors from 5:00pm, bars to 11:30pm | Chicago | 21+ One wristband, every bar on the Lincoln Park route, and no… [Details](https://thursday.kandr.io/r/1c3f2480c578e7b3?m=chicago&c=seo)
- **Lanterns and Legends: AAPI Market**: Sun, Oct 25 · 3pm · 1132 W Argyle St, Chicago · Free. Step into a magical autumn market celebrating Asian folklore, mythology & legends. [Details](https://thursday.kandr.io/r/890d2583d0ed7df3?m=chicago&c=seo)

## Family & Kids

- **Trick or Tunes: A FREE Sensory & Family- Friendly Concert**: Sat, Oct 24 · 10:30am · Merit School of Music, Chicago · See tickets. A Halloween concert featuring Merit's Wind Symphony designed for families and those with sensory processing sensitivities [Details](https://thursday.kandr.io/r/f9f9a78e7437d2b2?m=chicago&c=seo)
- **Costume Parade at \*play**: Sun, Oct 25 · 11am · \*play Hyde Park, Chicago · See tickets. \*play Hyde Park is hosting a children’s costume parade on Oct 25 from 11am to 12pm. Prizes for creative and DIY costumes. Open to all ages. [Details](https://thursday.kandr.io/r/86bc89f4a773ee09?m=chicago&c=seo)
- **Martina Jackson Erin Meets the School Counselor Book Signing and Talk**: Sat, Oct 24 · 6pm · Da Book Joint, Chicago · See tickets. Join Martina Jackson Erin for a fun in-person book signing and chat all about her newest book about Erin! [Details](https://thursday.kandr.io/r/84fd96c34a8cda57?m=chicago&c=seo)

## Outdoors & Sports

- **5k Fun Run x Spiteful Brewing | 2026 IL Brewery Running Series**: Sun, Oct 25 · 11am · Spiteful Brewing Tap Room, Chicago · See tickets. Join us for a 5k Fun Run on October 25 at Spiteful Brewing. Run, walk or jog a 5k course, then celebrate at the finish line! [Details](https://thursday.kandr.io/r/c6fe67e7c6f64ac7?m=chicago&c=seo)
- **ZUMBANDA**: Sun, Oct 25 · 1pm · DESTINO Event Space, Berwyn · See tickets. Chicago’s live banda workout experience bringing together movement, culture & connection! [Details](https://thursday.kandr.io/r/6398147473f797e7?m=chicago&c=seo)
- **ElPartidazo watch party: FC Barcelona vs Real Madrid - CHICAGO**: Sun, Oct 25 · 1pm · Moe's Cantina - River North, Chicago · Free. JOIN LALIGA and MICHEL SALGADO AT MOE'S CANTINA AND CATCH THE MOST EXCITING MATCH OF THE SEASON: FC BARCELONA vs REAL MADRID [Details](https://thursday.kandr.io/r/34bc976a4dc2864a?m=chicago&c=seo)

## Arts & Nightlife

- **Chicago Official Halloween Bar Crawl LIVE! River North and West Loop 2026**: Sat, Oct 24 · 4pm · Esco, Chicago · See tickets. Chicago's biggest Halloween Pub Crawl returns! Get tickets now for the best Halloween bar event in River North and West Loop Chicago. [Details](https://thursday.kandr.io/r/49264df4fb2cd2e2?m=chicago&c=seo)
- **Wild and Sublime LIVE in Chicago - EIGHTH ANNIVERSARY SHOW 10/25/26**: Sun, Oct 25 · 6pm · The Lincoln Lodge, Chicago · See tickets. Eight years running, sex-positive Wild & Sublime features steamy sexperts, standups, burlesque & storytellers bringing spicy laughs and more [Details](https://thursday.kandr.io/r/100df374234b284a?m=chicago&c=seo)
- **Trick or Drink: Chicago Halloween Bar Crawl (3 Days)**: Sat, Oct 24 · 4pm · Headquarters Beercade, Chicago · See tickets. Barcrawlerz is taking over Chicago this Halloween! [Details](https://thursday.kandr.io/r/8999d65231d6e1ea?m=chicago&c=seo)

## Free This Weekend

- **Chicago's Largest Playdate - Washington Park**: Sat, Oct 24 · 10am · Washington Park, Chicago · Free. Fall is officially here, and we are kicking it off with a celebration like no other. You’re Invited to Chicago’s Largest Playdate! [Details](https://thursday.kandr.io/r/8b3ff9c905fb9ff9?m=chicago&c=seo)
- **Arts in the Dark 2026 After Party**: Sat, Oct 24 · 7pm · 754 S Wabash Ave, Chicago · Free. Come party with us at the Columbia College student center after the Arts in the Dark parade! [Details](https://thursday.kandr.io/r/19a61eb3863c1bb5?m=chicago&c=seo)
- **Dorothy Pop! x Strapped!**: Sat, Oct 24 · 9pm · Dorothy, Chicago · Free. Dorothy Pop is a pop-focused dance party at Chicago's Lesbian Bar. Don't miss music, performances & a night of fun. [Details](https://thursday.kandr.io/r/bda581efb1f4cf90?m=chicago&c=seo)
- **Arts in the Dark**: Sat, Oct 24 · 6pm · North Columbus Drive, Chicago · Free. Join MoCP, Filter Photo, Latitude Chicago, and others as part of Arts in the Dark’s Photography Guild and parade. [Details](https://thursday.kandr.io/r/9c538ca452c9519d?m=chicago&c=seo)
- **Opening Reception: What Shall I Do With My Dead?**: Sat, Oct 24 · 5pm · Blanc, Chicago · Free. An exhibition on memory, archives, and honoring family legacy by Raja'Nee & Jalen Hamilton [Details](https://thursday.kandr.io/r/cbb3f796ea50cfa4?m=chicago&c=seo)

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